In the entire, brief history of hip-hop, a few moments have gone—as the saying goes—deeper than rap.
These are not the scenes and headlines that made hip-hop “relevant” as much as the moments where hip-hop characters, ideals, and narratives ended up on the front pages of national papers, shifting the American news cycle and making the sounds, lyrics, and faces of the genre as much a story as any great world leader or event. Sometimes, like Bill Clinton calling out Sister Soulja, the moments were gasoline on fire. Other times, they were just a spark on a fuse waiting to be lit, like Dr. Dre making headphones everybody’s most essential personal style accessory.
These are moments of protest, of struggle, and of shame. These are moments of pride and of power. These are moments that define the music we so often take for granted, whether it’s Kanye saying some shit about an American President, or an American President saying some shit about Kanye—and then campaigning with Jay-Z not long after. From the subliminal moments to the most pronounced, from the film and TV show moments to the moments when the corridors of political power were forced to confront rappers—yes, rappers—these are those times when hip-hop splashed into the mainstream, by all means necessary.
Hip-hop’s taken everything from figurative bows thrown to literal shots fired. Yet, they weren’t game changers for rap so much as for pop culture, moments of pure, uncut recognition that this isn’t just a subculture, or a trend, but pieces of the greater American mosaic. From Kanye to Clinton, from Style Wars to who Wu-Tang’s for, these are The 40 Biggest Hip-Hop Moments in Pop Culture History.
Written by Foster Kamer (@weareyourfek)
40. Blondie’s “Rapture” is the First “Rap” Video Played on MTV
Date: August 1981
The Moment: What happens when a punk band trying to spice up its repertoire attempts to do so by adopting what New York City punk bands—let alone pop culture—rarely ventured to for its hits? You get the first rap video on MTV, in MTV’s first month on the air, in their first 90-video rotation, which arrived in the form of Blondie’s “Rapture,” the entire coda of which is rapped by Debbie Harry. To hammer the point home, Blondie also recruited hip-hop luminaries to appear in the video with them, like Fab Five Freddy (who’s name-checked in the song), Lee Quinones, and Jean-Michel Basquiat.
The Impact: “Rapture” came at a weirdly perfect time as it wasn’t just the first video featuring rap on MTV, but was a video in MTV’s first real “rotation,” where it stayed for a few months. In other words, eyes from all over the country saw this young white woman doing the “hip-hop” thing.
The Upshot: At the time, it was neither an abomination nor a momentous occasion, but just a weird rock thing that was, if not amusing, then actually fairly cool. The video helped cement Blondie’s place as one of the more progressive bands in contemporary rock, and set the precedent for rock embracing hip-hop (and vice-versa).
39. Tone Loc Makes the Cover of Newsweek as the Face of Rap Rage
Date: March 19, 1990
The Moment: At the beginning of the new decade, Newsweek—then one of two magazines in every other suburban, middle-class household, along with Time—released a cover about the anger of rap music. The editors wanted to choose between two rap acts: LL Cool J, and Tone Loc. They went with Loc.
The Impact: Tone Loc didn’t become much “harder” of a rapper than he already “was.” The impact on Loc’s career was minimal at best. The cover’s effect on perceptions of rap, however, wasn’t insignificant. To one segment of America, it was a sign of things to come: Rap and these rappers are scary, it screamed, so you better lock away your children. To another segment of America, it screamed: People who write newsweeklies know nothing about rap, as evidenced by their selection of Tone Loc to represent anger in rap.
The Upshot: To another, much smaller segment of America, it screamed: Wow, scaring people with rap is pretty compelling. Let’s replicate it! And thus, thousands of fear-based pieces about the dangers of angry rappers were born, in a tradition that continues to this day. Meanwhile, Loc went on to have one of the most family-friendly careers in acting as a rapper has ever had, including famously being talked to by the ass of Jim Carrey in Ace Ventura: Pet Detective.
38. KDAY Hires Greg Mack (and Becomes America’s First True Hip-Hop Radio Station)
Date: July 1983
The Moment: Other stations had played rap before KDAY, but it wasn’t until the hiring of Greg “Mack” Macmillan as their program director and afternoon host that everything changed. Mack turned the station into a hip-hop powerhouse, recruiting young talent to not only to DJ, but to have their ears to the streets. One such talent pool? The World Class Wreckin’ Cru, whose Dr. Dre had started to mix tracks together on a mixer in real time, splicing old tracks into contemporary rap records.
The Impact: The station became one of the most influential outlets for rap nearly overnight, and broke some of the most important records in the history of rap. Moreover, it created the market for rap radio formats, and if hot rap singles begin anywhere, it’s on rap format radio.
The Upshot: KDAY would eventually turn over from a rap format station in 1991, and would relaunch as a less-influential version of the original in 2004 as a middle-ground urban contemporary station. More importantly, however, KDAY lead terrestrial radio executives to realize that the rap format would be a crucial one in years to come, spawning the creation of rap radio all over America.
37. Def Comedy Jam Premieres on HBO
Date: July 1, 1992
The Moment: Stand-up comedy—great, edgy, stand-up comedy—was still too hot for most televised broadcasts, let alone stand-up by black comedians, who had to overcome major networks’ worries about audience pull and standards and practices troubles. Enter Def Jam founder and label head Russell Simmons, who found himself with a production deal at HBO, that cable channel you had to pay extra for, with all the movies, and a few of its own TV shows that you couldn’t find anywhere else. Slapping his record label’s name on a late-night stand-up hour on pay cable, Simmons found a place to infuse comedians’ personas and performances with a hip-hop aesthetic, and create a home for unabated humor that was topical for a segment of the population that had long gone without one. In doing so, Def Comedy Jam was born.
The Impact: While protested by some for what was perceived as offensive content that reinforced negative black stereotypes, the show would go on to receive relatively high marks from TV critics.
The Upshot: Def Comedy Jam not only paved the way for edgy stand-up comedy on television, but cemented HBO’s place in the media world as an outlet for edgier entertainment, period. It also furthered Russell Simmons’ status as an entrepreneur of hip-hop outside of the realm of music, and gave rise to a host (Martin Lawrence) who went on to a wildly successful career of his own.
36. Vanilla Ice Makes a Cameo in the Ninja Turtles Movie
Date: March 22, 1991
The Moment: In 1991, Teenage Mutant Ninja Turtles II: The Secret of the Ooze was the smash of the summer. Helping its success was the presence of a rapper quite popular in his day, a Caucasian fellow better known to the world at large as Vanilla Ice, who performed his “Ninja Rap” in the middle of the movie, as part of the plot, assisting the Ninja Turtles in their fight against these guys.
The Impact: The move raised Vanilla Ice’s profile…among kids. It certified him as a pop star who managed to hang onto his moment, but took a severe toll on what little credibility he had with anything remotely resembling a “rap” audience. The film, however, grossed over $78 million at the box office.
The Upshot: The Ninja Turtles eventually feel out of popularity with young people in favor of Power Rangers, and then, Pokemon. Before then, they’d make two more films, one in 1993, and the next one in 2007 (which was entirely animated). Not only was Vanilla Ice in neither of them, but his own film, Cool as Ice, released just five months later, was a box-office bomb. Ice’s career went downhill from there: Drug problems, money problems, and issues with having a “harder” sound—or any sound, really—taken seriously. He had a brief nu-metal rap-rock revival in the late ’90s, only to eventually suffer the pitfalls of fleeting fame again. After an independent release here, and an independent release there, Ice is now featured on a reality television show about flipping houses. Despite all of this, Ice still finds appearing in the Ninja Turtles movie to be “one of the coolest experiences of his career,” which is funny, because it acts as a cautionary tale for any rapper who ever looked to cash in with too wide of an audience, too early into their career.
35. Bulworth is Released in Theaters
Date: May 15, 1998
The Moment: Academy Award-nominee and Hollywood royalty actor Warren Beatty writes, produces, consults with Suge Knight on, and directs a movie about a California Senator who goes off the rails, beginning to speak his mind and truth to his own power, in the form of cringe-inducing raps, with an all-star rap soundtrack released by Interscope.
The Impact: Like the titular character, the movie was initially seen as a curious and naive attempt by old white Hollywood to reach out to young urban America, both by Beatty’s Hollywood peers and casual viewers alike. As it turned out, both parties ended up loving it: Critics gave it generally positive reviews, the soundtrack produced one of the bigger hits of that summer (in the form of Pras, ODB, and Mya’s “Ghetto Supastar”), and the unlikely cultural crossover actually, oddly, managed to work out.
The Upshot: While it hasn’t aged so well and still can lay claim to one of the most universally reviled endings in ’90s movie history, the film grossed $29 million worldwide, and picked up a handful of nominations for Beatty and Jeremy Pikser’s screenplay (which only won a minor L.A. critics award, losing out almost universally to Shakespeare in Love or The Truman Show). The soundtrack was certified platinum by the RIAA. The movie was one of Warren Beatty’s last great works, as he continues to ease off major projects. A white person would not go on to rap in such a massive film until 8 Mile arrived in 2002.
34. Busta Rhymes and Martha Stewart Present a VMA Together
Date: September 4, 1997
The Moment: MTV rolled out one of the most unlikely pairings in the network’s history to present the 1997 VMA for Best Dance Video: Martha Stewart and Busta Rhymes, introduced by Chris Rock as “one [who] knows how to make a really mean pot roast, and the other one is always roasted on pot.” Martha showed up in muted browns, looking demure. Busta showed up in a red and gold kimono. “What the dilly, yo?” Busta grinned, as Martha Stewart looked both completely uncomfortable and also massively charmed. Martha talked about dropping some beats—or beets—and Busta shouted out Wu-Tang Clan and the Flipmode Squad. The entire thing was, in a word, surreal.
The Impact: It contributed to part a great year for both music videos and the Chris Rock-hosted MTV VMAs, which got high marks from TV and music critics as a high point in the brief history of the network and its awards ceremonies, and more crucially, MTV found itself encouraged to take bigger risks with pairings like Busta and Martha, especially after 1998’s Ben Stiller-hosted VMAs failed to thrill in quite the same way. Enter the ’99 VMAs, which were hosted again by Chris Rock, but this time, at the Met Opera, and had more than a few watercooler moments, like pairing the mothers of the Notorious B.I.G. and Tupac, or Lil’ Kim and Diana Ross, who would jiggle Kim’s pasty-covered breast on the VMA stage.
The Upshot: If, in 1997, you were asked who would spend more time in jail over the next fifteen years, you’d probably get this answer wrong. Busta Rhymes remained one of rap’s most popular and eccentric acts, and then got very, very in shape, and stopped wearing kimonos, and ceased being weird (and wonderful, to an extent). He never did hard time. Martha Stewart continued to grow her media and kitchenware empire, but did end up going to jail for insider trading. The VMAs fell into decline after the early Aughts, and have yet to reach quite the peak levels of excitement they generated in the late ’90s.
33. Fat Boys’ Swatch Commercials Air in NYC
Date: December 1985
The Moment: In 1985, as the holiday shopping season kicked into full gear, commercials for Swatch started appearing in New York City, featuring an unlikely celebrity endorsement: the Fat Boys, performing the song they’d recorded for the occasion, “Swatch Watch Presents A Merry Christmas.”
The Impact: After a Swatch-sponsored tour with Run-DMC, Kurtis Blow, and Whodini, the endorsement of the watch-slingers—made possible by the Fat Boys’ manager Charlie Stettler, a Swiss national—became one of the most successful cool-kid ad campaigns of all time, and shot the Fat Boys into the forefront of hip-hop as one of its most charismatic, charming, and irresistible acts.
The Upshot: The Fat Boys continued to appear in movies and TV shows (Disorderlies, an episode of “Miami Vice”) and made some classic records along the way. More importantly, they proved that rappers were as capable of being a celebrity spokesperson as any other stripe, and thus, paved the way for so many of the multi-million dollar deals we know all too well to come.
32. LL Cool J Pushes FUBU Into The Gap’s Commerical
Date: Spring 1997
The Moment: In the Spring of ’97, a commercial starts to air for the Gap, featuring a new kind of spokesperson for the mall-shopping standard of America: LL Cool J. In the spot, LL sports the Gap neck-to-toe. On his head, however, was a hat by a then little-known streetwear brand called FUBU, which stood for “For Us, By Us,” given a shout by LL in the lyrics of his rap during the commercial, with those exact words.
The Impact: Executives for The Gap were supposedly furious, once they actually realized what had happened. And here’s what happened: FUBU’s founder, Daymond John—an old friend of LL’s from Hollis, Queens—kept pestering LL Cool J to wear his new clothing line, until LL actually did…to a shoot for his big Gap commerical. Orders for the clothing line exploded, and FUBU became the original monolithic rapper-endorsed streetwear brand, with revenues totaling somewhere around the $300 million mark in 1998.
The Upshot: FUBU went on to inspire Sean Jean, Roc-a-Wear, et al. By the early Aughts, however, the clothing line had fallen out of style, and LL ended up suing FUBU for money he felt he was owed by the company.
31. Allen Iverson’s Bars Result in NBA Beef
Date: October 2000
The Moment: Hip-hop and the NBA had struck up a close relationship in the ’90s, with rappers befriending and endorsing various NBA players, who would in turn appear with rappers. The relationship reached a boiling point with the authorities that ran the NBA—and specifically, commissioner David Stern—when, right before the start of the NBA’s 2000-2001 season’s training camps, a Philadelphia radio station started playing “40 Bars,” a rap track recorded by 76ers star guard Allen Iverson. Among its lyrics: “Come to me with faggot tendencies and you’ll be sleeping where the maggots be” and “You man enough to pull the gun? Be man enough to squeeze it.” The song ended with the sound of a gun being cocked and a trigger being pulled.
The Impact: Public outrage ensued. Iverson would eventually decide to change the lyrics after being summoned to a meeting with NBA commissioner David Stern. On October 1, 2001, Iverson announced that he was putting the kibosh on his rap album and career.
The Upshot: Basketball players learned to be wary of their relationship with hip-hop, lest they invoke the wrath of the authorities that pay them. Furthermore, Iverson’s reputation as one of the bad boys of basketball was crystallized, something that would haunt him through the later years of his career, which would overshadow his on-the-court accomplishments in the press.
30. Theo Huxtable Raps on The Cosby Show
Date: October 22, 1987
The Moment: By 1987, The Cosby Show had become one of the most successful television sitcoms in history, and handily the most successful sitcom with a predominantly African-American cast. Yet, the Cosby kids seemed to stay frozen in time, and run slightly awry of what actual kids their age were doing and saying. Those actual kids had their attention taken from them that Fall, though, when, during the fifth episode of the fourth season of “Cosby,” Theo Huxtable and his friend Cockroach wrote a rap for a school assignment concerning the matter of Shakespeare’s Julius Caesar.
The Impact: In a show in which Bill Cosby had specifically avoided the (his words) “jive” parlance of the country’s African-American youth, the sight of one of America’s most famous teenagers rapping in their living rooms was a benchmark moment for kids and parents, further evidence to the entire country that rap wasn’t just a passing fad in a small segment of the culture, but something that would be coming to all families, everywhere.
The Upshot: Theo set the foundation for characters like the Fresh Prince to arrive, but The Cosby Show remained generally conservative when it came to addressing hip-hop culture head-on for the rest of its run, which amounted to five more years, and totaled six seasons (or 202 episodes), and is generally considered one of the greatest family sitcoms of all time. Malcolm-Jamal Warner, who played Theo, has kept up with acting (and yes, in the ’90s, dabbled in a brief music career that didn’t exactly pop off).
29. The Chicago Bears Debut the “Super Bowl Shuffle”
Date: December 11, 1985
The Moment: Believe it or not, the Chicago Bears were once a dominant force in pro football, especially in the ’80s, when they made a 15-1 regular season run. Even more incredible is the way they became a dominant force outside of pro football, thanks to a rap the team had written and recorded just after the 13th week of the season, the “Super Bowl Shuffle.”
The Impact: The single was a huge hit, as America’s fascination with the Bears’ almost-perfect run to the Super Bowl grew, and made it all the way to the 41st spot on the Billboard Hot 100. Unsurprisingly, the Chicago Bears remain the only professional sports team to accomplish this feat.
The Upshot: You can’t prove that the “Super Bowl Shuffle” helped the Bears absolutely clobber the Patriots in the Super Bowl that year, but they definitely did. The song was nominated for a Grammy (it lost, but still). A share of the profits from the record were donated to the Chicago Community Trust, which supposedly exceeded $300,000. Other teams would go on to try to replicate the success of the Bears (and their single), but none would come remotely close. Decades later, it would inspire one of the better oral histories the Internet has to offer.
28. PBS Airs Style Wars
Date: Fall 1983
The Moment: In 1983, as hip-hop culture continued its ascent into the mainstream culture, piquing the curiosity of the public, PBS aired a then-little known documentary about graffiti, breakdancing, and hip-hop culture titled Style Wars.
The Impact: The film—one of the first real looks into hip-hop as it was happening in New York City—wasn’t a smash ratings hit or a definitive moment for PBS, or even hip-hop. Its due credit would come with its legacy. In the short term, however, it did make the Rock Steady Crew, and artists like Dondi, Seen, Kase 2 and more into household names, at least for the households who saw it.
The Upshot: The movie lives in infamy as one of the most critically acclaimed films, not just about graffiti culture and its place in hip-hop, but an art form still very much on the rise, the likes of which very little else exists. It’s one of the great documentaries of the ’80s. It would be the first line in co-director Tony Silver’s obituary, and in the obituaries of several of its “stars.” In 2011, an effort to restore some of the old footage that wasn’t used in the film started as a grassroots campaign by co-director Henry Chalfant, and eventually met its goal via crowdfunding site Kickstarter.
27. Saturday Night Live Airs the “Lazy Sunday” Digital Short
Date: December 17, 2005
The Moment: As winter geared up, SNL tried to heat things up by teaming up then-young gun Andy Samberg with Chris Parnell (then about four years into his run) for SNL showrunner Lorne Michaels’ second attempt at what he labeled a “digital short”: A segment shot with digital cameras and edited on PCs, over the course of the SNLtaping week. The sketch—written with two new, young, and almost totally untested staff writers, Akiva Schaffer and Jorma Taccone—was pretty simple: Parnell and Samberg, angrily rapping over a hard breakbeat, explaining their Sunday routine of getting snacks, and smuggling those snacks into a screening of The Chronicles of Narnia.
The Impact: The clip was a smash hit, but as opposed to 2013, when Twitter and Facebook can make something go viral at light speed, the majority of humans who would watch an SNL clip still weren’t on one or both social networks, and “Lazy Sunday” ended up enjoying a slow, long, viral burn. Critics inevitably called it a high point for a show that’d been failing its legacy (as they always do with SNL). The clip was played on radio stations and racked up five million hits on YouTube—which, in 2005, was a lot—before being pulled by NBC three months later and thrown on Hulu. Everyone from middle schoolers to their uncool parents spent the next six or seven months quoting, “The Chronic-WHAT-cles of Narnia.”
The Upshot: “Lazy Sunday” helped do quite a few things: Shoot Andy Samberg to immediate SNL hall-of-fame status, make the creation of Digital Shorts a regular priority, help secure the comedy trio of Sanberg, Schaffer, and Taccone—better known to the world as The Lonely Island—a major label record deal, which would result in the group winning a Grammy for another smash Digital Short, “I’m On a Boat.” It also spawned a bunch of terrible response videos and parodies on YouTube, a classic segment on The Office, and the less-than-memorable “Lazy Sunday 2” in 2012.
26. MC Hammer’s Pepsi Ad Hits the Airwaves
Date: Winter 1990
The Moment: Filmed on the campus of the University of Tennesee over three days, MC Hammer’s biggest endorsement started to air around Thanksgiving of 1990. It was an ad for Pepsi—the extended version of which ran a full minute—in which the rapper starts singing “Feelings” after having his Pepsi switched out for Coca-Cola. Given a Pepsi by an audience member, Hammer returns to rapping and dancing, and being MC Hammer, in 1990.
The Impact: The endorsement was one of several at the time that added to Hammer’s bankability, and was one of the largest rapper-endorsement deals in history, at that point. Sure, it did wonders for Pepsi, but it inflated Hammer’s bank account to such an absurd degree that he didn’t know what to do with it. Literally, Hammer (officially) went broke in 1997, crying poor with $13.7 million in debt, and only $9.6 million in assets to cover it.
The Upshot: While debates about Coke vs. Pepsi rage on to this day, another one runs a little more under the cultural radar: whether or not criticism of Hammer for taking the Pepsi endorsement money (and the sellout label) was fair. For one, deals like Hammer’s are de rigueur for rappers in 2013. So what’s so wrong with a little paper? Purists argue it destroys any semblance of artistic intent or merit. Whatever side you’re on, know this: Hammer seems to be living a satisfied life without all the cash, but it came at the price of hip-hop credibility.
25. Common is Invited To Read Poetry at The White House
Date: May 9, 2011
The Moment: In the Spring of 2011, a White House pool report came out about a poetry reading, hosted by Michelle Obama. It was nothing out of the ordinary, until conservative news outlets came across it, and went on to have a field day. Common, a Chicago rapper, was part of the reading.
The Impact: Never mind that Common isn’t the striking image of Scared White America’s Angry Black Rapper, or that his biggest hits are about love, art, and elevating one’s social consciousness. Outlets like Fox News and The Daily Caller went wild, with their pundits posting and reciting context-free samples of Common’s work to make the rapper sound less like less Common. Eventually, outlets started reporting that Common had voiced his support in song for Joanne Chesmard, a Black Liberation Army member convicted of killing a cop in cold blood in 1977 for a murder that, in his words, she couldn’t have done. Jon Stewart and The Daily Show produced one of the show’s most memorable attacks on Fox News, ever, as Stewart rapped about the stunningly absurd and hypocritical way Fox News was playing this story out.
The Upshot: White House press secretary Jay Carney briefed the press corps before the event, explaining that while the president didn’t always agree with or even enjoy specific sections of Common’s lyrics, he had kind words for the rapper’s overall body of work. The performance by Common proceeded as scheduled a few days after the “controversy” unfolded, and Common was given a hug by President Barack Obama as the event wrapped up. Stewart not only critiqued the White House’s soft-power handling of the situation on The Daily Show, but also ended up on The O’Reilly Factorembarrassing the show’s titular blowhard over the way his network handled the entire thing. Then, of course, Barack Obama got re-elected.
24. Ol’ Dirty Bastard Explains Who Wu-Tang is For
Date: February 25, 1998
The Moment: After being nominated for Wu-Tang Forever, Shaolin’s finest lost the Best Rap Album Grammy to Puff Daddy & the Family’s No Way Out. Wu-Tang didn’t lose for Song of the Year—they weren’t even nominated for it—but later that night, when Shawn Colvin took the stage to accept the award for her adult contemporary hit, “Sunny Came Home,” she didn’t just win a Grammy, but a surprise from Wu-Tang Clan member Ol’ Dirty Bastard. He took the mic—in front of the award’s presenters, Erykah Badu and Wyclef Jean—and on live television, explained to a stunned-silent crowd: “Please calm down, the music and everything. It’s nice that I went and bought me an outfit today that costed a lot of money, you know what I mean? ‘Cause I figured that Wu-Tang was gonna win. I don’t know how you all see it, but when it comes to the children, Wu-Tang is for the children. We teach the children. You know what I mean? Puffy is good, but Wu-Tang is the best. Okay? I want you all to know that this is ODB, and I love you all. Peace!”
The Impact: Dirty left the stage to hilariously light, mannered applause, leaving a great watercooler moment, and some decent tabloid fodder in his wake. Wyclef told reporters after that show: “O.D.B. will be remembered as the legend, the man in the red suit.” While Dirty apologized to Shawn Colvin in an MTV interview (“I apologize, my darling…I think it was her speech that really attracted me up to the stage at that point in time to do that. So, no disrespect at all. Thank you,” even though Colvin hadn’t even started her speech yet), when asked by MTV if that was the best place to express that specific viewpoint, Dirty stuck to his guns (“Yes”). The next day, the New York Daily News tried to pathetically imply that the stage-bombing was part of a bigger beef between Bad Boy and Wu-Tang, calling it “the latest salvo in the long-running war of words between his group, Wu-Tang Clan, and Sean (Puff Daddy) Combs.”
The Upshot: He gave the world what might be the most hilarious acceptance speech-bombing in award show history, and he gave Wu-Tang the most press the group had received since he rolled up to a welfare office to pick up his check while he still had a top 10 album. The thing is: Wu-Tang really was for the children. This happened during the same week that Dirty also saved a little girl who was trapped under a car. Mind you, this was the same Grammy ceremony that saw Bob Dylan receive a “SOY BOMB.” The events combined turned what would’ve been an otherwise unmemorable awards show into one of the greatest in the awards show canon. Diddy’s next album was called Forever, which wasn’t a reference to the Wu, but it’s a noteworthy coincidence.
23. Eazy-E Attends White House Luncheon with President George H.W. Bush
Date: March 18, 1991
The Moment: It’s the ultimate moment in “WTF” rap trivia: The L.A. Times breaks the news that Eazy-E—founding N.W.A member, singer of “Boyz-n-the-Hood,” yes, thatEazy-E—had been invited to the White House by then-Republican Senate leader Bob Dole for a luncheon. The Republican Senatorial Inner Circle would be in attendance, with George H.W. Bush, the President of the United States of America.
The Impact: The American media outrage machine wasn’t as fast in 1991 as it is now. In other words, by the time most people got the news, Eazy had already finished up lunch. With Bob Dole. And President George H.W. Bush. And by the time they did receive the news, it had already become the stuff of legend. The moment was so unbelievable, it was literally unbelievable, made all the more difficult to process by the fact that no pictures exist of Eazy at the lunch.
The Upshot: Republicans and fans of Eazy-E alike were stunned: How could the sitting American President allow this gangster rapper into the White House? and Eazy-E is a Republican? The Bush White House, for their part, decided to kill the matter by never commenting on it. Eazy did, however, explaining in an interview: “How the fuck can I be a Republican when I got a song called ‘Fuck tha Police’? I ain’t shit—ain’t a Republican or Democrat. I didn’t even vote. My vote ain’t going to help! I don’t give a fuck who’s the president,” and later, explaining in song: “So, you can kiss my black ass/Fuck the White House, it ain’t my house/So, you can burn the mothafucka down for all I care/Cause T-shirts and khakis is all I wear.”
While history accuses Eazy—who eventually died of AIDS, not exactly a conservative cause in the ’90s—of being a Republican, the urban legends about this are wrong, as Jerry Heller explained in his book Ruthless. Eazy had donated to a South Central charity event. His name was picked up by an RNC computer mailing list, which hit Eazy up with an invitation, which Eazy accepted. We’ll let Heller’s book speak for itself, because the truth of the matter is so, so great:
“…As it turned out, we had a pretty okay time. We ate poached salmon and roast beef. (Eazy E) sat next to a woman from Dallas, who I would bet had never mixed socially with a person of color before in her long and well-heeled life. I expected her to start talking about ‘the problem of the Negro.’ I think she was actually afraid to look at the short African-American next to her, so she didn’t notice that (Eazy E’s) eyes looked like a couple of all-black marbles. “Nobody’s been that stoned in the White House since Gerald Ford’s kid Jack smoked dope on the White House roof. And Eazy had better weed that Jack Ford ever did.”
22. Cam’ron and Dame Dash Are Booked as Guests on The O’Reilly Factor
Date: November 12, 2003
The Moment: Dipset is not exactly the kind of rap act prominently known for its consciousness or political activism. Yet, there was Cam’ron, somehow on The O’Reilly Factor debating the social and artistic merits of hip-hop with one of the most infamous blowhards in American history, alongside Dame Dash, no less. Along for the ride was an inner-city Philadelphia elementary school principal, who objected to the chosen profession of the two men, with O’Reilly acting as mediator/instigator.
The Impact: Whoever booked this for Bill O’Reilly’s deserves a special award. Let’s just say the conversation got really interesting, really fast. The first words out of Cam’ron’s mouth were mocking Bill O’Reilly’s description of his music. Killa Cam deadpanned to the camera: “Pimping. And bitches.” It only got better from there. If you desire the full effect, feel free to read along with the transcript or watch the video. Suffice to say, what happened was nothing short of amazing. Bill O’Reilly was shouted down, for one of the only times on his show, by Cam’ron in a way that, if not effective, was at the very least, hilarious. “Why don’t you want to let him talk? You mad. You mad.”
The Upshot: It may not have been rap’s finest moment in the world of politics, but the video would quickly went viral among rap fans, Dipset fanatics, and the political media, who rarely got a look into what defeating Bill O’Reilly on his home court looked like. It wasn’t the most dignified victory, but it was still an incredible one. It set the precedent for what happens when you put Cam’ron on “serious” television, until 2007, when he was interviewed by Anderson Cooper on the matter of snitching (and how, even if he lived next door to a serial killer, never would he ever).
21. Cypress Hill Lights Up, Becomes the First Rap Act to Be Banned by SNL
Date: October 2, 1993
The Moment: The first critically and commercially successful Latino hip-hop group was on the rise with the release of their second album—and what would remain the crowning achievement of their career—Black Sunday. On SNL, the group delivered a so-so performance of “Insane in the Brain.” For the second song, after being introduced by that week’s host, Shannon Doherty, Cypress Hill launched into “I Ain’t Going Out Like That,” except with a side-note from DJ Muggs: “Yo, New York City, they said I couldn’t light my joint, you know what I’m saying?” [Takes hit from joint.] “Well, we ain’t going out like that!” [Takes even harder hit from joint.] The group then kicked off a riveting performance, and destroyed a few of the instruments on set before they were done.
The Impact: Here’s a little background: Apparently, they didn’t light up just because they were Cypress Hill (a totally plausible theory otherwise, though). To hear DJ Muggs tell it, the producers kept whispering into the in-ear monitors of the group, telling them not to light any joints on stage. And kept telling them. And kept telling them. Apparently, they told them one time too many. As soon as Muggs sparked up, the phones at NBC starting ringing: As many middle schoolers and high schoolers were thrilled, there were pissed off parents in equal proportion. Moral outrage or not, Saturday Night Live showrunner Lorne Michael had a strict anti-drug policy in place, at least as far as the workplace was concerned. They were informed that they were banned from Saturday Night Live for good. Needless to say, they made a few Monday morning newspapers, too.
The Upshot: You can’t watch the clip on NBC’s site, but it made its way into legend on the Internet. While the rest of the group might’ve been upset with Muggs, it launched them into a special kind of infamy: the small group of guests who have been banned by SNL for life, which has included at various times Sinead O’Connor, Elvis Costello, Chevy Chase, Martin Lawrence, Milton Berle, and the Replacements. “I Ain’t Going Out Like That” was nominated for a Best Rap Song Grammy. Cypress Hill kept making albums, none as memorable as Black Sunday, but they had later hits. SNL is still on today, and hasn’t banned any other rap acts since.
20. John Connor Wears A Public Enemy T-Shirt in Terminator 2: Judgement Day
Date: July 3, 1991
The Moment: In what was billed as the biggest action movie of all time, there was 14-year-old southern California teenager Edward Furlong playing 14-year-old southern California teenager John Connor, protected by a robot sent from the future—as played by future California governor Arnold Schwarzenegger, in what would go on to become his most iconic film role—as he is hunted down by a much angrier robot sent from the future to kill him (so he doesn’t go on to lead the human rebellion against the machines).
Just a little under a year before the Rodney King riots would set L.A. ablaze, the robot trying to kill John Connor, the T-1000, was donning the disguise of totalitarian authority incarnate: an LAPD cop. How perfect, then, that John Connor sports a shirt blasting one of the most politically rebellious music groups (let alone rap acts) of all time: Public Enemy, who also happened to have a DJ named Terminator X.
The Impact: The most politically vocal rap group of all time had suddenly been blasted into the consciousness of anyone who’d see the movie, which, as it turned out, was everyone. The movie made $519 million worldwide, and every single one of those people got a pretty clear message: White kids from the suburbs who go on to save the world in the robot wars of the future are really into Public Enemy, so do with that what you will.
The Upshot: While the movie was bashed by conservative culture critics (remember those?) for its epic gun violence and not-always-family-friendly language, John Connor became and remains one of the most memorable teenage movie heroes (or sidekicks) of all time.
A few months after the movie came out, Public Enemy released the critically and commercially successful Apocalypse 91: The Enemy Strikes Back, which charted all the way up to the fourth spot on the Billboard 200. It also happened to feature a metal band of white Jewish guys (Anthrax) tearing up a re-release of Public Enemy’s “Bring Tha Noize” with the group at the end of the album, which, while not diluted from the group’s signature styles, handily reached a larger audience than any Public Enemy album before it.
19. Chappelle’s Show Airs the First Lil Jon Skit
Date: February 25, 2004
The Moment: On the second season, in the sixth episode of what was quickly catching fire as the hottest comedy show of the new decade, Dave Chappelle aired a sketch of himself, as rapper-producer of the moment, Lil Jon, living a day in Lil Jon’s life.
The Impact: “I’m Rick James, bitch,” might’ve been the Chappelle’s Show line that everyone knew, but for those who listened to rap, who knew Lil Jon’s mannerisms by way of videos or interviews, this was the greatest of Chappelle’s impersonations: comically over-exaggerated, painfully topical, and a hilariously accurate. In other words, pitch-perfect.
It lent the show further credibility with both casual and slightly more devoted hip-hop fans. With Questlove as house DJ, and acts like Kanye West, Talib Kweli, Big Boi, Common, Snoop Dogg, and Mos Def either performing tracks or acting in sketches, Chappelle was able to connect with all levels of rap fandom. More importantly, it proved that rappers could take a joke: Lil Jon later appeared on Chappelle’s Show as himself, with Chappelle and Lil Jon playing Lil Jon, in what turned out to be one of the show’s greatest moments.
The Upshot: 2004 turned out to be Lil Jon’s most successful year, and his distinct voice and production reigned over popular rap through 2005, fading off in the mid-to-late aughts. The second season of Chappelle’s Show became one of the most critically-acclaimed bodies of work in comedy, but Chappelle later walked away from a $50 million dollar deal while taping the third season, citing a spiritual, psychological, and philosophical burnout.
Over seven years later, and Chappelle’s still only doing standup routines here and there, as the world waits for his great return. Lil Jon’s still releasing music with popular acts, though he’s not as prolific as he once was. He did, however, return to TV on The Celebrity Apprentice, making it all the way to the show’s Final Four before losing.
18. Kanye Jumps The Jumpman with Air Yeezys
Date: April 4, 2009
The Moment: On April 4, 2009, Nike released its first non-athlete collaboration shoe with rapper, producer, and trending style icon Kanye West. Titled the “Air Yeezy,” the shoe ran in a limited edition of 3,000 pairs, and retailed at a price of $215.
The Impact: The debut of the Air Yeezys was the most high-profile limited edition sneaker launch in the history of footwear. Lines started around stores selling it days before it went on sale, with people camping out to get their hands on a pair.
The Upshot: The Air Yeezy immediately became one of the most desired sneakers in the world, as did the second edition, with valuations for the Air Yeezy and the Air Yeezy 2 still exceeding over $2,000. Furthermore, it solidified Kanye West’s place as one of the great contemporary fashion icons of our time, and one of the most influential people in rap both within and aside from record sales.
17. Three 6 Mafia Wins an Oscar
Date: March 5, 2006
The Moment: At the 2006 Academy Awards, previously only rap-famous Memphis group Three 6 Mafia became the first rap artists to perform at the Oscars after “It’s Hard Out Here for a Pimp,” the song they’d written for 2005’s Hustle & Flow, was nominated for the Best Original Song Oscar (it went on to win).
The Impact: The win was the only mainstream movie accolade for Hustle & Flow, but its status as the first real non-pop rap act Oscar winner not only made Eminem’s win for “Lose Yourself” from 8 Mile pale in comparison, but it sealed the reputation of Hustle & Flow as one of the more legendary entries in the hip-hop film canon.
The Upshot: The Academy’s move to award the song was widely seen as a progressive step for the organization, which has since gone on to shake the old ways of awarding “Oscar-movies” and instead beginning to recognize films that had equal parts impact with critics and with the general public (like Heath Ledger’s performance in The Dark Knight, or The Departed or Argo winning Best Picture).
The highbrow love for Three 6 Mafia started a renaissance for the group that’s paid in dividends since. They got a cut on Justin Timberlake’s smash 2006 album FutureSex/LoveSounds (“Chop Me Up”). They had a minor hit of an MTV show in 2007. And just last year, founding group member Juicy J’s solo cut “Bandz a Make Her Dance” was a smash hit. In other words, given the opportunity to prove that their win wasn’t a fluke, they did.
16. J-Lo and Diddy Leave the Scene
Date: December 27, 1999
The Moment: At Club New York in Manhattan, just as the new millenium was about to arrive, the old one’s hottest power couple of the moment—pop star/actress/erstwhile fly girl J-Lo and rapper/producer/media mogul Diddy—ducked out in the midst of total pandemonium after shots were fired in the club. And yes, there was a gun in the car that they left in.
The Impact: Diddy and J-Lo were arrested by the NYPD as the action unfolded, on account of that gun that was found in the 1999 Lincoln Navigator the duo tried to escape in with Diddy’s bodyguard (much to the total, unrestrained glee of the tabloid press). Also, the fact that they ran through 11 red lights on their way may have helped speed the arrest process along.
Regardless: Jennifer Lopez was promptly let go, claiming no knowledge of the weapon that was in the car. Diddy, his bodyguard (Anthony Jones), his driver (Wardel Fenderson), and Jamal Barrows (better known as Shyne) were all charged, however. The first three got busted on account of the gun, which had been stolen from somewhere in Georgia a few months prior to the incident. Shyne, though, was charged with firing the bullets in the club (someone had said something not-so-nice to Diddy, and another had thrown a stack of cash). The tabloids had a field day with this for quite some time.
The Upshot: Diddy, with the help of superlawyer Johnnie Cochran, was acquitted of his charges (which included bribing his bodyguard to lie on his behalf), along with his bodyguard. Shyne went to jail for 10 years and emerged from prison only to be deported (as he’s a naturalized citizen of Belize), and became an Orthodox Jew. Diddy and J-Lo broke up, and J-Lo moved on to a string of high-profile relationships (Ben Affleck, Marc Anthony) and high-profile career bombs (such as starring in Gigli with Ben Affleck).
Oh, and those three total bystanders who were shot? Diddy quietly settled their civil suit against himself and Shyne out of court, for a pretty six-figure sum.
15. Lauryn Hill Dominates The Grammys
Date: February 24, 1999
The Moment: At the 1999 Grammys, former Fugees member Lauryn Hill’s first solo effort—the commercial and critical smash hit The Miseducation of Lauryn Hill—was nominated 10 times, and won five of those awards: Best New Artist, Best R&B Song, Best Female R&B Vocal Performance, Best R&B Album, and Album of the Year, which was most notable, as it was the first rap album to win the award.
The Impact: Hill’s Grammy sweep was seen as one of the more accurate, fair, and generally correct moments of the Grammy voting committee. The wins put her on the map to an entire contingent of music listeners who hadn’t already heard her album, mostly made up of people who didn’t regularly listen to rap or R&B. Sales of the album skyrocketed, and it went on to sell 19 million copies worldwide.
The Upshot: The year after, Hill won an Album of the Year Grammy for her co-production of Santana’s star-studded Supernatural, making her the only female artist to win this prestigious award twice consecutively. In February 2001, she settled a 1998 lawsuit with artists who she’d failed to properly credit on Miseducation, reportedly paying $5 million.
Disliking what she felt success had done to her life and psychology, Hill went into seclusion following Miseducation‘s outsized success, and didn’t release another album until an emotional solo performance on MTV Unplugged 2.0. She’s since dabbled with a short-lived Fugees reunion, songwriting, and strings of live appearances here and there, but nothing even remotely resembling the worldwide acclaim (and thus, attention) she received after the Grammys.
14. “Fight The Power” Becomes Do The Right Thing‘s Anthem
Date: June 30, 1989
The Moment: In 1989, what remains one of the most incredible years in movies—Indiana Jones and the Last Crusade, Batman, Back to the Future: Part II, The Little Mermaid, and Driving Miss Daisy, to name a few—one release stuck out among all of them: Brooklyn film director Spike Lee’s Do the Right Thing. The movie more or less revolved around a crackling (and in the movie, literal firestarter of a) rap song, commissioned by Spike Lee just for the film: Public Enemy’s smash, “Fight the Power,” heard over a boombox carried around by one of the film’s crucial characters, Radio Raheem.
The Impact: The track caught fire that summer, hitting the top spot on the Billboard rap chart, and was a smash hit with critics as well. The Do the Right Thing soundtrack peaked at the 68th spot on the Billboard Hot 100, and of course, the film didn’t do too bad, either. (It received two Oscar nominations and was selected for preservation in the National Film Registry in its first year of eligibility, one of just five films to be so honored.)
The Upshot: The song has since become the standard-bearer for political rap anthems, and furthermore, the use of rap in film. Public Enemy later recorded the title track for the soundtrack of Spike Lee’s He Got Game, giving the group a much-needed publicity boost in 1998.
13. Dr. Dre Has Some Headphones He’d Like To Sell You
Date: January 6, 2008
The Moment: Cool looking, high-quality headphones weren’t a must-have item for most music listeners in 2008: They were something you needed, a tool to make your mobile device work, one that sometimes looked cool, but not much more.
At the 2008 Consumer Electronics Show in Las Vegas, that changed when legendary rapper and producer Dr. Dre—who was more or less absent from the greater music conversation at the time—re-emerged with a new act: Dr. Dre, headphone salesman. And not just a headphone salesman, but one with the finest set of headphones everyone from old ‘heads to audiophiles had ever seen, Bose be damned. They had Dr. Dre’s endorsement. They played bass. He sat at the studio console with them. They had a red cord. What else did anyone need to know?
The Impact: On July 25, 2008, the first model of Beats by Dre—the over-ear “Studio” model—went on sale for $349 (tax not included). They got decent to not-halfway-badreviews, with most audiophiles citing the significant bass factor missing from most headphones at the time. They were a busting-the-ball-at-the-seams smash.
Early adopters of Beats turned out to be on-trend, as celebrity endorsements—including Lady Gaga and Lil Wayne—followed, which is to say nothing of the legions of rappers, singers, actors, and athletes who weren’t being paid to sport them. Towards the end of 2011, helped by the release of several new (and cheaper) models, annual sales were reported to be somewhere in the $500 million range. From headphones. Safe to say, Dr. Dre and Jimmy Iovine had found their biggest hit ever.
The Upshot: Monster Cables didn’t make out so well from the deal when Dre and Jimmy let Taiwainese electronics monolith HTC bring its money in, and broke up with Dre and Jimmy (or, more likely, got broken up with) at the beginning of 2012. But the two rap moguls certainly did, both when HTC put $300 million in, and then again, when HTC sold half its majority ownership stake (thus giving Jimmy and Dre majority control over the company).
Beats by Dre changed the headphone game by turning something essential, but never coveted as an item, into a household luxury item. It could fairly be likened to the music fan’s version of bottled water (or at least, if not the headphones, then the hand-over-fist cash Jimmy and Dre made).
More importantly: Who needs the rap game when you’ve got headphone money? Not Dre, who has yet to make another album since 2001, or the long-awaited-and-probably-never-happening Detox. That said, he will step in to drop bars on the occasional star-studded track and, yes, plug the shit out of his headphones.
12. Bill Clinton Responds to Sister Soulja
Date: May 13, 1992
The Moment: In the ’92 election, Clinton faced a press crisis explicitly concerning the African-American contingent who would ostensibly elect him over his Republican opponent, sitting president George H.W. Bush. In an interview published by the Washington Post, black activist and MC Sister Soulja—in response to a question about whether or not the ’92 L.A. riots were “wise” or not—asked “If black people kill black people every day, why not have a week and kill white people?” Soulja had previously explained in a music video “If there are any good white people, I haven’t met them.”
Enter Clinton, who, while delivering a speech to Jesse Jackson’s Rainbow Coalition, noted of Soulja’s remarks that “If you took the words ‘white’ and ‘black,’ and you reversed them, you might think [white supremacist] David Duke was giving that speech.”
The Impact: The quip was an attempt by Clinton’s campaign to distance himself from Jackson, who wasn’t all that popular with “moderates” or “undecideds,” and some of his more extreme politics. Naturally, Jesse Jackson was pissed, and attacked Clinton for taking on Soulja over what he considered a mis-contextualized quote. Sister Souljah released a statement lambasting Clinton as a draft-dodger, a reefer-smoker (her words), and someone who supports the lobotomy of prisoners, among other things.
The Upshot: The impact of Clinton’s take on Sister Souljah is still being debated—whether or not there was one, and what it was—but one thing is indisputable: African-Americans helped elect Clinton not once, but twice. Sister Souljah went on to become a lecturer and successful urban lit author. But more importantly, the term “Sista Soulja Moment” grew out of the controversy, going on to define any instance in which a political candidate distanced themselves from what they might consider to be an uncomfortably extreme association with elements potentially considered unsavory by waffling voters.
11. Kanye West Interrupts Taylor Swift
Date: September 13, 2009
The Moment: At the 2009 MTV Video Music Awards, as a 19-year-old Taylor Swift began to deliver an acceptance speech, having beaten out Beyoncé’s “All The Single Ladies” for the Best Female Video award with “You Belong With Me,” Kanye West took to the stage, grabbed the microphone, and made Internet history. He exclaimed: “Yo Taylor, I’m really happy for you, I’mma let you finish, but Beyoncé had one of the best videos of all time. One of the best videos of all time!”
The Impact: West was removed from the VMAs for the rest of the night. Later in the ceremony, Beyoncé and Taylor Swift appeared in matching dresses, and Beyoncéceremoniously give Taylor Swift time to deliver an actual acceptance speech. Kanye West quickly became an object of scorn and meme-ification for the universe over the next week, as Taylor Swift took to morning shows and aired Yeezy out. At one point, even President Barack Obama remarked in an off-the-record interview that went public calling Kanye West a “jackass.”
The Upshot: Kanye West went into self-imposed exile to make what’s widely seen as the best album of his career, My Beautiful Dark Twisted Fantasy, but not before hitting a few talk shows on the way to deliver teary apologies about the place he was in at the time (still mourning the death of his mother, for example). He also made several attempts to apologize to Taylor Swift both publicly and privately. She finally accepted his apology at the next year’s VMAs in the form of what was widely regarded as a massively patronizing performance.
That same night, Kanye delivered a widely heralded premiere performance of his most self-loathing song, “Runaway.” Eminem got a great lyric out the incident, on a single “No Love” (“Man, get these whack cocksuckers off stage/where the fuck is Kanye when you need him?/Snatch the mic from ’em, bitch/I’mma let you finish in a minute”). Race scholars would have plenty to chew for the next few years as the image of an angry black man stealing the spotlight from a seemingly innocent young white woman was stamped in the legacy of both artists, MTV, and pop culture for the rest of time.
Swift and ‘Ye reconciled in the form of a low-five on the floor of the Met Costume Ball in 2011. And in 2012 and early 2013, Swift’s reputation as an innocent began to fade as she continued to write patronizing and exploitative songs about men who had wronged her, while Kanye West’s softer side emerged on national television as Americans watched him date and impregnate Kim Kardashian.
10. Florida Judge Outlaws 2 Live Crew’s Nasty As They Wanna Be
Date: June 6, 1990
The Moment: In light of an anti-porn crusade by Miami lawyer Jack Thompson that captivated the public’s attention, Florida governor Bob Martinez ordered state attorneys to look into whether or not sales of 2 Live Crew’s Nasty As They Wanna Becould be banned under the state’s obscenity laws. And then, on June 6, 1990, the verdict came in: Guilty of being too nasty for Florida. In his opinion, Judge Gonzalez wrote that the group profited from “an appeal to ‘dirty’ thoughts and the loins, not to the intellect and the mind” and that the album “appeals to a shameful and morbid interest in sex.”
The Impact: In the days leading up to presiding Judge Jose Gonzalez’s verdict, Broward County sheriff Nick Navarro had threatened to arrest store owners found to be selling the record, before it was even outlawed. Once it was deemed obscene, Navarro went ahead and arrested record store owners selling the album, and then after a live show, cuffed the members of 2 Live Crew, after sending cops into a local concert in an undercover sting operation. News of the verdict and especially the arrests made national headlines.
The Upshot: 2 Live Crew was eventually acquitted by a jury of all obscenity-related charges. Nearly two years later, in May 1992, Judge Gonzalez’s verdict was roundly overturned by the U.S. 11th Circuit Court of Appeals in Atlanta, posting a big fat L for the moral crusaders against rap. Not that it mattered. The ban made 2 Live Crew hotter than ever, and what was considered to be “obscene” rap had already started to take ahold of young cultural undercurrents in America, and past that, the world at large. The losers left behind a legacy of failed puritanism. The winners went on to inspire some of the greatest twerking anthems of all time.
9. Yo! MTV Raps Debuts
Date: August 6, 1988
The Moment: In the summer of 1988, over half a decade into its premiere on cable networks, MTV aired the first episode of a two-hour television block exclusively dedicated to rap music.
The Impact: Yo! MTV Raps was the first show to give exclusive time to rap videos, and thus, proliferated the market for them. Doctor Dre and Ed Lover became two of MTV’s most famed VJ’s overnight, and an appearance on MTV Raps was a must for any rap act on the rise or of the moment. The show became enshrined in plenty of rap songs, though ratings would begin to slip a few years into its existence once competition (like BET’s Rap City) started to emerge as serious contenders for its audience.
The Upshot: Yo! MTV Raps had a fruitful, seven-year run and became a crucial component of early ’90s rap culture. The show’s creator, Ted Demme, went on to direct some critically and commercially successful films (Life, Blow) before dying of a heart attack at 38. Ed Lover and Doctor Dre continued to be old-school hip-hop luminaries in day jobs as radio hosts after the end of Yo! MTV Raps. MTV made several attempts at replicating the success of MTV Raps—including a 1999 reboot of the original show—but none popped off quite the same as the original.
8. Run-DMC Walks Aerosmith’s Way
Date: July 4, 1986
The Moment: It was clear that rap was quickly becoming an incredible force in pop music by the mid ’80s. Record companies were getting to the point of not being able to get enough, especially where crossover with a white audience was concerned.
The stars lined up for RCA, though, in the summer of 1986: Aerosmith, a soaring ’70s rock band hitting the skids in the ’80s both creatively and logistically—having dealt with a bevy of inner-band conflict and Olympic-level drug abuse—needed a hit. Run-DMC simply needed a new hit, and wanted to achieve that next level of fame, bigger than rap, bigger than hip-hop, bigger than America. What emerged—thanks to Rick Rubin, who brought the idea to a reluctant Run-DMC—was “Walk This Way,” a single released on July 4th, 1986, featuring the Queens-bred rap trio breaking beats and spitting rhymes over a scratched-up and mixed sample of Aerosmith’s original mid ’70s hit “Walk This Way.”
The Impact: The song exploded. It became the first rap song to break the top five on the Billboard 100, charting all the way to the fourth spot (higher than Aerosmith’s original ever did).
The Upshot: The track remains one of the most famous cover songs of all time, and the most early precedent of rock and rap acts mixing together successfully. It also spawned a memorable video, which tends to rank about as high and as often on rap lists, rock lists, and ’80s lists as the song itself does.
7. Public Enemy’s Professor Griff’s Anti-Semitic Interview
Date: May 22, 1989
The Moment: After non-rapping Public Enemy member, “Minister of Information,” and road manager Professor Griff supposedly made anti-Semitic remarks in a series of British interviews, David Mills at The Washington Times spoke to Griff for the paper. When asked about who controls the music industry, Griff explained that “Jews have a grip on America” and also that they were the cause of a “majority of wickedness that goes on across the globe.” And then, on June 14, 1989, The Village Voice‘s RJ Smith picked up on the interview. Which is when it really hit the fan.
The Impact: It would be an incredible understatement to note here that this did not go over well. More accurate would be “one of the most massive shitstorms in rap, ever,”which didn’t have much to do with the fact that Def Jam founder Rick Rubin is Jewish (he was out of Def Jam by then), or the fact that Lyor Cohen, their manager, was Jewish and Israeli, which is to say nothing of their label publicist at the time, Bill Adler (yep: Jewish).
It was a few things: For one, Chuck D was calling up rap writers around the country—RJ Smith at the Voice, David Mills at The Washington Times, John Leland at Spin—and trying to threaten and bully them out of keeping up with the story. It didn’t work. The story was too hot. Griff’s comments were too blatant, unilateral, defined, and unapologetic to simply ignore.
For another, the Jewish Defense League had lined up a massive grassroots boycott of Public Enemy and started firing away (the play: listening to Public Enemy associated you with anti-Semitism). Really, the question of post-mortem on Griff’s comments is what didn’t happen: Public Enemy was declared broken up by their record company and by the JDL.
On June 19, 1989, Chuck D declared Griff still in Public Enemy, but not as Minister of Information. On June 21, 1989, during a press conference, Chuck D announced that he had fired Griff. Then Chuck D declared they were back together. Griff had been condemned, apologized for, defended, and kicked out of Public Enemy by Chuck D.
The Upshot: When later asked if he ever believed everything he said about Jews, Griff supposedly told former Def Jam vice president Bill Stephney: “No, that’s just silly. I was just having a bad day. I was mad at the group.” Griff apologized and made amends with the Jewish community he’d offended. Public Enemy continued to grow as an act in the pop culture and rap canons—hell, “Fight the Power” came out later that summer—but their reputation would never be the same initial one of an unimpeachably righteous rap act. The interview was one of the defining moments of David Mills’s career, which included a stint writing for David Simon’s Treme before he passed away in 2010.
6. The Fresh Prince of Bel-Air Debuts on NBC
Date: September 10, 1990
The Moment: The first prime time sitcom to star a rapper aired on NBC in September of 1990, produced by super-producer Quincy Jones, no less. That rapper? The 21-year-old Fresh Prince (a.k.a. Will Smith), and that show—about a kid from the West Philadelphia hood, sent to live with his well-off aunt and uncle in Bel-Air—was The Fresh Prince of Bel-Air. And it opened, of course, with Will Smith rapping the show’s theme song.
The Impact: The series debuted with a 13.6 rating, which was massive for a new show with a young, untested actor relatively new to television. If you were young, you loved it. Adults and critics, on the other hand, didn’t love it, at least not at first. Three major complaints: (1) Will Smith’s acting chops weren’t quite there yet, (2) the deeper issues at play went untouched, and (3) as the New York Times put it, “It seems that a good many viewers may not necessarily like the idea of solid upper-middle-class citizens being turned into buffoons to be sneered at by a smart aleck.”
By the start of the third season, Fresh Prince—being shown on Monday nights with Blossom—was the highest-rated sitcom among the highly-coveted teenage demographic. And Will Smith, who had almost gone bankrupt by the time the show aired due to reckless spending of record deal money and an IRS debt, was restored to a decent degree of financial health. It also was the beginning of the acting career that came to define so much of Smith’s reputation.
The Upshot: The writers continued to shift the balance between comedy and drama for the rest of the show’s run. For more than five years and six seasons of television, Fresh Prince challenged ideas about class differences, race, comedy, hip-hop’s place in the contemporary African-American landscape, and beyond that, ’90s American landscape.
The show, which became one of the most widely syndicated sitcoms in television history, transformed Will Smith from a rap star into a pop culture star, as he started to take dramatic film roles (Six Degrees of Separation) and blockbuster action roles (Independence Day, Men in Black). The theme song remains one of the greatest and most recognizable theme songs in all of television, and during the late ’90s, he resumed a wildly successful rapping career.
Another sign that the show had an impact: Almost all of the show’s stars who weren’t Will Smith were never be able to completely divorce themselves from their roles on Fresh Prince. Word to Carlton.
5. The Beastie Boys’ Licensed to Ill Drops
Date: November 15, 1986
The Moment: Just before Thanksgiving in 1986, Def Jam via Rick Rubin suddenly dropped something the world had never seen before: A rap album…by three white, Jewish kids who used to play in a punk band.
The Impact: The album was a nihlistic, party anthem-filled ode to mischief, hedonism, wiseassery, that spoke in its own language, both figureatively and literally. Rap albums hadn’t been recorded with the kind of hard guitar riffs and concrete-cracking bass drops in the same hand that were on this Def Jam masterpiece; until then, Blondie’s “Rapture” was the closest thing the world had seen to a white person rapping, let alone rapping in a way that would make most parents concerned about the moral fabric of America want to literally lock up their daughters.
The album received rave reviews and went platinum only four months after its release in February 1987. It turned the Beastie Boys into overnight stars, and some of the most terrifying young men to influence teenagers in the history of American pop music.
The Upshot: The Beastie Boys moved away from their image as America’s Greatest Hellraisers as they progressed through their careers, eventually apologizing for some of the most outright misogynistic parts of the album (especially of note: “Paul Revere,” which they stopped performing with the same lyrics). But the album—which brought rap into the mainstream in an unprecedented way—was just the beginning of one of the most legendary rap careers of all time. Licensed to Ill opened the doors for not only white rappers who wanted to be taken seriously, but also rappers who wanted to take a serious approach to artistic evolution over time.
4. Jay-Z Campaigns For And Introduces Barack Obama At Ohio Rally
Date: November 5, 2012
The Moment: The night before America’s 2012 presidential election, Jay-Z appeared at Barack Obama’s final campaign rally in Ohio, alongside Bruce Springsteen. Hov hit the stage and performed “Public Service Announcement,” “On to the Next One,” “Run this Town,” “Encore,” and “99 Problems,” subbing in the word “Mitt”—as in Obama’s Republican opponent Mitt Romney—in place of the word “bitch” on the chorus, before introducing Barack Obama.
The Impact: Everyone on Twitter freaked out and tuned in to the livestream, with music writers everywhere calling it a breakthrough for rap and politics. Whereas Jay had performed at the 2008 Inauguration during a relatively informal party, the American President explicitly lining himself up with the Roc was no small deal.
Conservative pundits immediately used it as a case against Barack Obama, citing Jay-Z’s past as a crack dealer and the lyrics in “99 Problems” about evading cops. Rush Limbaugh personally took to the air the next day to lambaste both Jay-Z and Obama, and made his case by reciting the lyrics of “99 Problems,” in what will stand the test of time as the single worst performance of the song in all of recorded history. That said, people had other things to worry about that day, like, for example, a Presidential Election.
The Upshot: Barack Obama? Handily re-elected President of the United States of America by a wide margin, especially with the help of Ohio. Ann Romney blamed the media for her husband’s loss, but her defeated man reflected upon the fact that he “failed to reach minorities,” let alone the youth vote or middle class that came out for Obama in droves.
Conservative columnists kept blasting Obama’s friendship with Jay-Z, calling him an “ex-con entertainer” and the like. A few months later, Jay rapped on Kendrick Lamar’s “Bitch Don’t Kill My Vibe (Remix)” and explained: “In the White House with a mink/Running through that bitch like it’s my house/All up in the hall like a mall/Told you motherfuckers, all I do is ball.” Also, he may have admitted to standing next to former Secretary of State Hillary Clinton high as a kite: “Sittin’ next to Hillary smellin’ like dank/Presidential pardon, name one ni**a out there harder than him/I’ll wait.”
3. Eminem and Elton John’s Duet at The Grammys
Date: February 21, 2001
The Moment: Two albums in, and Eminem had simultaneously become an international pop star, a critical darling, and the target of every special interest group known to man (except for, maybe, the ACLU). Liberal, conservative, it didn’t matter. Eminem could offend the conservative moral majority and GLAAD on the same song. Imagine the world’s outright shock, then, when Em not only performed his somber fan-gone-bad anthem “Stan” with gay icon Elton John at the 2001 Grammys, but when Eminem and Elton John also embraced, held hands, and raised them together at the end of the performance.
The Impact: As GLAAD continued to object to Eminem’s ostensibly homophobic lyrics via protest outside the Grammys, the performance was already being celebrated by fans and critics alike as one of the greatest pop culture water-cooler moments of the new decade. Two incredible artists—seemingly at odds with each other musically and socially—joined together. It set a high bar for bringing nuance into dialogues about what musicians should and shouldn’t sing, do, or say: Elton John had crossed the gay cultural picket line for Eminem, and Eminem had shrugged off rap’s (still) conservative ideas about gay men in America with ease.
The Upshot: In the end, both Eminem and Elton John saw more acclaim than fallout over the matter, upsetting whatever previous expectations of them should do. The moment brought a renewed interest in younger audiences for Elton John and older audiences for Eminem, who won an Academy Award (something, it could be pretty reasonably argued, that he would have never seen without his Elton John collaboration coming before it).
The friendship between Eminem and Elton John continued for the next decade: In 2010, it came out that Elton John had been helping Eminem kick his addiction to prescription drugs. In 2011, Elton John told Rolling Stone that Eminem gave him and his husband two “diamond cockrings” as a wedding present.
2. Kanye West Calls Out George W. Bush
Date: September 2, 2005
The Moment: During a live telethon in the aftermath of Hurricane Katrina—a disaster of unprecedented proportion, both in physical scale and what was generally seen as the American government’s failure to respond well to it—Kanye West went off-script and told the camera “George Bush doesn’t care about black people.”
The Impact: One half of the country labeled Kanye West a bigot, a racist, and an exploitative attention hog. The other half nodded its heads in agreement. Whichever side people took, however, it was undeniable that after that everything, from the debate about the government’s response to Katrina to the debate about (A) the government’s response to Hurricane Katrina and those affected by it as well as (B) the place celebrities have in the public forum, had changed forever.
The Upshot: George W. Bush later called that the low point of his presidency. Kanye apologized to Bush, later recording a lyric on Watch The Throne about raising his son as a Republican, “so everybody know he love white people.” And poor, hapless Mike Myers, who was pleading for donations alongside Yeezy and was blindsided by the political statement, later vented to Kanye about the problems he caused him on a classic Saturday Night Live moment, and also, appeared with Myers as a friend of his in the classic Myers flop The Love Guru.
1. 2Pac And The Notorious B.I.G.’s Murders
Date: 2Pac: September 13, 1996 / Biggie: March 9, 1997
The Moment: On the night of September 13, 1996, Tupac Shakur and Suge Knight left the Mike Tyson-Bruce Seldon boxing match at the MGM Grand in Las Vegas. On the way to their car, they got into a brawl inside the hotel. On the way to a club, a white sedan pulled up next to Suge and Tupac, not three blocks from the Las Vegas strip, and fired multiple gunshots at them, killing Shakur. Knight lived.
Less than six months later, the Notorious B.I.G. was on a trip to Los Angeles to promote his upcoming album and appear at the Soul Train Awards when a driver pulled up to the rapper’s convoy 50 yards from the awards show after-party and a gunman fired several shots, hitting Big four time. After the rapper was rushed to the hospital, doctors pronounce him dead less than an hour later.
The Impact: “Earth-shattering” would not be overstating the case. After Shakur’s death, the rap media—which had already been fanning the flames of an east coast-west coast rivalry—declared this an outright act of war, specifically between the L.A.-based Death Row Records and New York-based Bad Boy Entertainment. 2Pac was cast as a martyr by his fans, and by the rest of America, as empirical evidence of rap’s uber-violent culture caving in on itself. Bad Boy vehemently denied any involvement in Shakur’s death.
After the Notorious B.I.G.’s death, the rap world imploded in a state of mourning, with all parties decrying violence. Big’s Life After Death, released less than three weeks later, became one of the most critically and commercially successful rap albums of all time, selling 690,000 in its first week, eventually earning Diamond status certification from the RIAA.
The Upshot: On a smaller scale, Death Row Records entered a state of decline following the death of Tupac. Bad Boy flourished as the domineering force in rap for a couple of years thereafter, but eventually other rap scenes and crews (Roc-a-Fella, No Limit, So So Def) took over trendsetting for the genre. On a larger scale, everything changed.
Like John Lennon, Marvin Gaye, Jimi Hendrix, Janis Joplin, Otis Redding, and so many before them, the deaths of Tupac Shakur and the Notorious B.I.G. are held up in music history as two of the art’s greatest and most preventable losses, and the worldwide reverberation was on a scale in the ’90s only matched by the death of Kurt Cobain in 1994.
Both artists released posthumous albums—in ‘Pac’s case, several—and absurd conspiracy theories about their murders (e.g. ‘Pac was still alive; B.I.G. was done in by Diddy) persisted. Several suspects, trials, and wrongful death claims later, and neither murder has been definitively solved by the L.A.P.D., who were accused of everything from negligence to outright cover-ups.
The shootings were an indictment of rap’s lyrical violence, manifest in its culture, as well as the media and fans who were complicit in escalating the conflict, and spoke to a larger issue about the state of and reasons for urban violence in America, and to this day, still forces the entire culture of hip-hop to consider what a reckless culture of violence could mean for all of us.
No outsized “beef” since has lead to the kind of fatal violence Big and ‘Pac faced. And on September 9, 1999, the mothers of both rappers, whose legacies and influence on contemporary music is still seen today, appeared together on stage at the 1999 MTV VMA’s, the closest and saddest thing the world would ever get to a sense of closure and resolution on the matter, holographic nonsense notwithstanding.
SOURCE: FOSTER KAMER