After Hip-Hop’s mid-’80s mainstream breakthrough, the tropes and aesthetics of rap music were suddenly thrust into the commercial spotlight. Of course, that would eventually bring Hip-Hop to the forefront as the dominant cultural influencer for the generations who came of age as it took flight.
But in the ’80s and much of the ’90s, the mainstream public’s lens for Hip-Hop was limited. Even as Hip-Hop stars of the late ’80s gained high-profile critical acclaim with artists like Public Enemy and N.W.A. fostering the genre’s rebel image while acts like De La Soul were hailed for quirky eclecticism, many mainstream entities still seemed to engage with rap music as a novelty or an oddity.
Here are 10 of the most unforgettable (we tried, we really tried) moments when Hip-Hop crossovers made for woeful results.
No. 10: Rappin’ Cartoon Characters
Blaster of Transformers
For a generation of ’80s kids, cartoons like The Transformers and G.I. Joe were mainstays of their weekday afternoons. These merchandised toy fests of pop culture played a major role in signifying Hip-Hop’s growing trendiness. Popular Black characters on many popular action cartoons of the day were saddled with stereotypical tropes (there was even a G.I. Joe character who wore a basketball jersey and only spoke in hoop speak), and the rapping hero soon became an ’80s cartoon cliché.
The Transformers had Blaster, a communications export for the good-guy Autobots — a boom box who often spoke in rhyme: “Give us some answers and make it snappy, ’cause my buddy here’s trigger-happy.” Roadblock of G.I. Joe was the most prominently featured African-American character, and he also spoke in rhyme: “Play it straight or there’s no doubt, I’ll turn your eyeballs inside out.” He became one of the franchise’s most popular characters, famously portrayed by Dwayne Johnson in the 2013 movie G.I. Joe: Retaliation.
No. 9: Novelty Rap Singles
Rappin’ Rodney
Goofy singles would pepper the pop charts of the ’80s and ’90s and — were it not for its rapid expansion and diversification, often independent of the biggest commercial stages — could easily have pigeonholed the genre by the “Disco-Duck”-ing of its popular image. The mid-’80s, in particular saw jokey tracks like comedian Rodney Dangerfield’s legendary “Rappin’ Rodney,” the Chicago Bears’ terrifying-but-endearing “Super Bowl Shuffle,” and the John Wayne-themed “Rappin’ Duke.”
Imagine if you’d never heard of Grandmaster Flash but this kind of thing was your initial exposure to rapping and Hip-Hop? And it wasn’t just one-off joke records churning out novelty hits. The Fat Boys had some of Larry Smith’s best production values and very real charisma, but were soon devoured (bad pun, right?) by an image predicated on cartoonish silliness of gimmicky songs like “All You Can Eat” and oldies covers like “Wipe Out” and “The Twist.”
Part of the reason some people underappreciate DJ Jazzy Jeff & the Fresh Prince’s legacy as a DJ-MC duo is because of novelty singles like “I Think I Can Beat Mike Tyson” and “Nightmare on My Street.”
But there was a string of movie-themed duds like the Fat Boys’ “Are You Ready for Freddy” from A Nightmare on Elm Street 6, the Teenage Mutant Ninja Turtles theme song “Turtle Power” by the annoyingly named Partners in Kryme, and Vanilla Ice’s infamous “Ninja Rap” from the Turtles’ sequel.
Far more successful smashes like MC Hammer’s “Addams’ Groove” from The Addams Family and Will Smith’s “Men in Black” kept novelty rap on the charts well into the ’90s, but as Hip-Hop became more centered in popular culture, more people recognized these kinds of songs for what they were: fun, slick, junk food.
These songs aren’t anything close to definitive now, but for many, these types of songs were their first window into Hip-Hop.
No. 8: Toy Commercials
Rappin’ Rockin’ Barbie
Madison Avenue embraced Hip-Hop’s selling power in the ’80s and ’90s by producing rap-centric products. That still goes on today, but some early attempts at rap cross-marketing were downright strange.
In a 1992 commercial, Fred Flintstone and Barney Rubble became a rap duo in an effort to sell Fruity Pebbles cereal. Rappin’ Rockin’ Barbie didn’t turn out to be the toy craze of 1992, but the commercial from that year highlights the way Madison Avenue tried to connect with Hip-Hop for the sake of commerce with dance moves and a goofy boom box that “Plays a real rap sound!”
And who could forget the 1993 video game commercial for The Legend of Zelda: Link’s Awakening? Taking a decidedly hard-core slant on a decidedly non-gangsta game was an interesting choice, with production that wouldn’t have sounded out of place on a Das EFX record from around that time.
No. 7: Saturday Night Live’s Attempts at Hip-Hop Parody
“The Princess & The Homeboy”
You can’t parody what you don’t know.
That’s a truth of comedy. There’s a fine line between landing a funny punch and whiffing at it because you’re swinging at something from the outside. You have to really get it well enough to poke at it, and SNL’s attempts to mock Hip-Hop were typically awkward and unfunny pre-Y2K.
Take SNL’s 1996 sketch “The Princess and the Homeboy,” which featured Tim Meadows as a foul-mouthed houseguest of Mark McKinney and host Teri Hatcher. It opens with the warning:
“Get ready America, because next Monday there’s a surprise in store for the Fresh Prince and for LL COOL J. You see, a new brother is moving to the hood, and he’s as legit as they come!”
The skit centers around a sitcom featuring a rapper named G-Dog, who comes to the live with a white-bread couple. McKinney’s character explains: “When G-Dog’s father passed away I promised him that G-Dog could live with us.” G-Dog proceeds to yell offensive things at the couple like, “I’ll thank you to shut the fuck up, and go make me a muthafuckin sandwich!” Because, y’know, that’s rappers!
The G-Dog character seems like the kind of rapper created by folks who didn’t know hip-hop well enough to effectively mock it. Meadows plays him like a randomly cursing Freedom Williams of C+C Music Factory. Going from Compton to the country club, indeed. SNL’s contemporary Hip-Hop shots are far more on-target and funnier.
As the raunchy Hip-Hop soul of acts like Jodeci took over as the sound of ’90s R&B, SNL decided to spoof the lick-you-up-and-down vibes of acts of the era. Given that Chris Rock is involved, you would think the 1993 parody “Suck Your Big Toe” — a send-up of Hip-Hop- drenched R&B acts like Jodeci, Silk, and H-Town — would hit harder or be funnier.
No. 6: Rapping in the Movies
Tom Hanks and Dan Aykroyd “City of Crime”
As Hip-Hop hit the charts in the mid-’80s, it also hit the big screen and not just in rapsploitation classics like Breakin’ and Beat Street. It popped up in weird and expectedly awkward scenes in other movie genres. There’s the earnest-but-lame freestyling scene from Say Anything… , which scores points for authenticity. Nothing’s more real than four white high-school guys rapping in a convenience-store parking lot.
But there were even more egregious offenders. Sticking a goofy rap into a popular comedy or kitsch flick became a bit of a go-to formula. We would all be happier to erase from existence Dan Aykroyd and Tom Hanks’ atrocious “City of Crime” rap from Dragnet. We all love Hanks, but somebody should be made to answer for this one.
And the less said about the better about the 1986 video “The Karate Rap,” which appeared in the 1994 forgotten martial arts film Sister Sensei. And we may never forget the “Lambda Lambda Rap” from the finale of Revenge of the Nerds.
While the next entry could fit neatly into this category, it’s so notorious it deserves special recognition.
No. 5: Suburban Rap Oddity ‘Teen Witch’
“Top That!” from Teen Witch
So bad, it merited its own standalone spot.
It’s hard to describe Teen Witch, the 1989 fantasy-comedy white-rap musical. There’s so much bad suburban white-kid rap in this movie it’s kind of amazing. Highlights include a crew of bros rhyming their come-ons from their jeep to star Robin Lively and an infamous rap-dance scene performed by Noah Blake as the character of Rhet.
Many of the principals involved with Teen Witch explained on People TV in 2018 how that scene came to be.
“They wanted to redo the opening of the movie, and they really wanted to come up with a big rap song in the middle of the movie as a feature,” shared Teen Witch score composer Larry Weir. “So the new producers I met with said ‘Do you write rap?’ and I said ‘Yeah, I’ll write a rap.’ So I went home and worked on a rap.”
After Weir debuted the song to a raucous reception from the producers, they reshot the movie to include the scene. So they spent more money to make sure this made it into the movie.
“We had wrapped Teen Witch and all was well,” explained actress Mandy Ingber, whose character Polly is clearly impressed by Rhet’s funky dancing and rhymes. “I felt like it was a few months later, I got a call and they wanted to add some new scenes to the movie.”
Actor Blake knew immediately how cringe-worthy it all was going to be.
“I do remember walking out of the dressing room onto the set and thinking ‘Wow, this is really pushing the envelope of whatever this is supposed to be,’ ” he explained in ’18. “There was not any moment in time that I ever thought what I was doing was cool. There was no moment that I was ever not in peril that this was would be just totally humiliating.”
No. 4: Karl Lagerfeld Goes Hip-Hop
Karl Lagerfeld’s 1991 Fashion Show
In 1991, legendary fashion designer Karl Lagerfeld debuted his latest creations for Chanel, and it became evident that the Fall 1991 Chanel fashions were heavily inspired by the Hip-Hop trends of the early ’90s.
“I think what Lagerfeld has always done amazingly well is completely capture the mood of the moment,” explained style.com editor-at-large Tim Blanks. “He listens to everything, reads everything, sees everything, and then distills it into these incredibly potent fashion images. In this collection, you get a sense that he was probably listening to rap music.”
Lagerfeld gave rappers props during the show. “The rappers are more clever, and you cannot fool them. The make-believe and all this doesn’t work anymore. You can’t cheat nobody anymore. I think it’s a good thing.”
Baseball caps worn backwards, long chains, baggy pants — they were all there. It was definitely high fashion. Was it Hip-Hop? Not sure. The looks are undeniable, but it’s hard not to wonder how much Hip-Hop fashion he’d actually absorbed up until then. Lagerfeld proved to foreshadow what would become an industry unto itself — couture fashion’s flirtation with Hip-Hop. Some people might side-eye.
But hey, at least they’re not bad looks.
No. 3: 9021-Yo and Grandmaster B
Married With Children: Best of Grandmaster B
In the early ’90s, teen stars on Fox started pining for Hip-Hop cred. Could it have been because Fox was the most Hip-Hop-friendly of the networks at the time? It was home to Martin and In Living Color, but two of the network’s biggest stars began flaunting their supposed Hip-Hop cred as their shows became ratings smashes.
One was Beverly Hills, 90210 star Brian Austin Green. His character, David Silver, was written to match his own interest in rapping and DJing, and both became heavily referenced aspects of the character throughout the show’s run. After several false starts, he actually dropped an album — 1996’s One Stop Carnival — produced by SlimKid3 of Pharcyde. There’s also a video for his quasi alt-rappy single “You Send Me.”
But if you somehow missed David Silver’s wannabe-Hieroglyphics rhyme career in the ’90s, you may recall Married With Children’s David Faustino’s foray into the rap game. Playing the popular character Bud Bundy on the hit sitcom, Faustino used his fame to bolster Hip-Hop among the LA elites, opening one of the first rap clubs on the Sunset Strip in the early ’90s. On the show, the writers took note of Faustino’s rap interests and wrote them into his character. Thus, Grandmaster B was born.
Grandmaster B was nerdy Bud Bundy’s rapper alter ego. Both a parody and a full-on representative of the kinda goofs who’d made Vanilla Ice a star, Grandmaster B makes you wonder how many people actually got the joke.
No. 2: “And the Winner is … ”
Vanilla Ice Wins Best New Artist
Hip-Hop has an awkward history with music awards shows. Kanye West spent the majority of the ’00s ranting about it. Diddy decided to call it out in ’20. But the Grammy Awards and American Music Awards have always had a weird relationship with Hip-Hop, and it’s not limited to the infamous ’89 ceremony and MTV’s Hip-Hop boycott of that show.
You can’t expect an institution like the Grammys to dig deep for the most underground classic rap shit, but those popular awards shows had a specific lens — especially in the ’80s and ’90s — that was almost exclusively squared on whatever big crossover rap hit made waves, even if that hit was by Candyman.
You have Vanilla Ice winning Best Rap New Artist at the 1991 American Music Awards, which led to him being booed at the Soul Train Awards a few weeks later. Grammy-winning rappers of the ’80s and ’90s include Young MC, MC Hammer, Sir Mix-A-Lot, Coolio, and Will Smith (three times). To be fair, artists like LL COOL J, Salt-N-Pepa, Dr. Dre, and Queen Latifah all took home gold gramophone awards, but the Grammy organization, which promotes the show as “Music’s Biggest Night,” seemed to have a narrow idea of mainstream Hip-Hop in any given year. When you consider the historical context, the Grammys’ contemporary criticism has long, deep roots.
Today, more Hip-Hop fans tune in to the Grammys than ever before, so the criticism is louder than it was decades ago. Is change imminent? Hope so.
No. 1: Rapping—So Easy, Anybody Can Do It?
Jay-Z on Oprah
One of the common misconceptions about Hip-Hop — specifically the art of rapping — in the earlier years of its crossover was that anyone can rap. The pervasive thinking among the older generation was that rapping was just talking over a beat, and as such, you got many lame and condescending “So show me how to rap” incidents across pop culture. Sheila E.’s terrible rhyme from Krush Groove was cute in the film’s context but also showed how musicians can sometimes dismiss the art.
And there was the JAY-Z appearance on the famously anti-Hip-Hop Oprah Winfrey’s talk show back in 2009 showing the icon how to rap.
It also didn’t help that as other genres embraced Hip-Hop, they also embraced the idea of rapping on their own songs. We got years of bad raps from many performers, like the Pet Shop Boys and En Vogue, until someone got the brilliant (we’re not exaggerating here) idea to include actual rappers on such songs. Because as cool as anyone may think it is, not everyone can rap.
Artists like Jody Watley, LeVert, Janet Jackson, and even Sinéad O’Connor and R.E.M. reached out to actual rappers like Rakim, Heavy D, MC Lyte, and KRS-One to guest on their tracks before Mariah Carey’s ’95 hit “Fantasy” featuring Ol’ Dirty Bastard turned the approach into a winning formula for pop success. From that point on, big hits meant featuring big rappers. But the beginning was dark. No one ever has to hear Donnie Wahlberg’s rap from New Kids on the Block’s single “Games” ever again.
* Banner Image: CREDIT: Vanilla Ice / Photo by Michel Linssen/Redferns