1. Debbie Harry gets jiggy wit it with "Rapture" (1980)
Yes, yes, we know: "Rapture" is a seminal song from a legendary band, and it played a huge role in popularizing hip-hop among the rock, new wave, and uptown crowd. But it should also be noted that lead singer Deborah Harry delivers her "rap" (sample lyric: "Go out to the parking lot / And you get in your car and you drive real far") is delivered with a precious "Look ma, I'm rapping!" obliviousness that paved the way for regrettable hip-hop excursions from overconfident, underqualified rockers like Todd "TR-i" Rundgren and Madonna. "Rapture" sent out the patently false message that anyone could and should rap, and a legion of rockers, athletes, comical grannies, prehistoric cartoon characters, and precocious penguins unwisely rose to the challenge. "Rapture" has a good beat and you can co-opt black culture to it.
2. Richard "Crazy Legs" Colon does body-double work for Jennifer Beals in Flashdance (1983)
In the '80s, breakdancing maintained a high profile in film, both as the subject of breaksploitation masterpieces like Breakin' 2: Electric Boogaloo and as a cheap, flashy gimmick in countless low-budget romps and zany comedies. In 1984, breakdancing went blockbuster when the legendary Richard "Crazy Legs" Colon strutted his stuff alongside his Rock Steady crewmembers in a not-at-all-gratuitous breakdancing sequence, then donned a leotard and wig so he could body-double for Jennifer Beals during part of the climactic audition sequence in Flashdance. After all, nothing wows the snooty old gatekeepers of classical dance quite like a well-executed backspin.
3. The Super Bowl Shuffle (1985)
Like mirthful protagonists in an old MGM musical, the 1985 Chicago Bears were overcome with emotions so bold, brassy, and outsized that they could only be expressed in song. But what genre would the boys use to express their Super Bowl dreams? Prog rock was too wonky, punk rock too abrasive. Norwegian death metal would only scare the fans. So the shuffling crew laid down a rap delineating the iconoclastic personalities of the team, from Walter "Sweetness" Payton (thusly named because "he likes to dance" and also equates "running the ball" with "making romance") to back-up quarterback Some Dude (whose name and rap are both lost to the ages). The surprise smash made rap safe for blue-collar football fans, while laying the groundwork for countless terrible subsequent albums from athletes.
4. Barney and Fred get rappy (late '80s/early '90s)
In Ronald Reagan's heyday, movies weren't the only medium cynically exploiting what they clearly viewed as a passing fad no different from Pet Rocks or voting rights for women. Hip-hop and breakdancing popped into commercials throughout the '80s, most notoriously in an infamous commercial for Fruity Pebbles. In this clip, O.G. Barney Rubble dons by-then slightly anachronistic Run-DMC-inspired gear to trick Fred Flintstone into giving him a bowl of cereal. Here, Barney learns the valuable lesson that if you want to deceive a chum, it's best not to rap out loud about how you're intent on tricking him.
Shockingly, this wasn't Fruity Pebbles' sole dalliance with hip-hop, as this second MC Hammer-style clip clearly illustrates. How many times must Barney trick Fred by pretending to be a famous rapper before he catches on?
5. Vanilla Ice pays respect to the Green Machine with "Ninja Rap" (1991)
The late '80s and early '90s were a golden age for hip-hop, and for clueless hip-hop theme songs to kid-themed movies. Who can forget (or for that matter, remember) Bobby Brown's awkward "rap" from his Ghostbusters II theme song, or Hammer's similarly dated "Addams Family Groove"? But no rap theme song quite matches the shameless cheesy bad-goodness of Vanilla Ice's immortal "Ninja Rap" from Teenage Mutant Ninja Turtles 2: The Secret Of The Ooze. Fans should be aware, however, that at no point in the song does Ice ever actually reveal the secret of the ooze. Vanilla Ice qualifies as the living embodiment of the clueless co-option of hip-hop, so it's only fitting that he appear on this list twice.
6. Big Daddy Kane and Vanilla Ice get naked for Madonna's Sex (1992) With the possible exception of fellow shape-shifter David Bowie, Madonna is pop culture's preeminent vampire. She sinks her lady-fangs into the neck of hot young things and leaves them as drained husks. Case in point: Vanilla Ice and Big Daddy Kane, both of whom had thriving careers when they doffed their duds for Madonna's controversial Sex photo-book, only to watch their fortunes wane in the aftermath. Vanilla Ice never boasted any credibility in the first place, but Kane was well-regarded until his would-be power-move with Madonna backfired. His career has never recovered.
7. Duran Duran slaughters "911 Is A Joke" (1995)
In 1995, a rejuvenated Duran Duran decided to pay homage to their influences with the covers collection Thank You. The disc boasts stellar versions of Bob Dylan's "Lay Lady Lay" and The Doors' "Crystal Ship," as well as two songs no aggregation of insanely rich middle-aged white men should ever touch: the anti-cocaine message song "White Lines" and Public Enemy's "911 Is A Joke." Duran Duran's version lacks the humor and freshness of Public Enemy's original, but it did bring much-needed attention to the discrimination that wealthy white British rock stars face when trying to secure ambulances in a foreign country.
8. Granny raps her way into America's heart in Wedding Singer (1998)
Hey, you know what's hilarious? The '80s. You know what else is hilarious? Old people rapping. That seems to be the thinking behind the buzzed-about "Rapping granny" sequence in Wedding Singer, where a gleeful old biddy romps her way through Sugarhill Gang's "Rapper's Delight." A hip-hop-happy grandma might seem comically incongruous, but if entry number one has taught us anything, it's that everyone can and should rap.
9. The Bush sisters give OutKast mad/embarrassing props (2004)
For the 2004 Republican convention, speechwriter Karen Hughes needed a "hip" contemporary pop-culture reference to brighten up the Bush sisters' "comic" speech, which was designed to radically alter their public personas from lightweight, dim-witted, hard-drinking party girls to lightweight, dim-witted, hard-drinking party girls capable of stiffly reading terrible jokes from a Teleprompter. After no doubt consulting a 14-year-old nephew, Hughes dreamed up a stilted bit of wordplay for Jenna about how her parents may be square, but they aren't so out of it that they don't realize that this newfangled "OutKast" entity is a "band" and not "a bunch of misfits." Also, apparently when pressed, the President and First Lady will "shake it like a Polaroid picture." The Bush sisters' reign as distaff Marx brothers was understandably short-lived. As Mr. Show's Professor Murda might put it, science was insufficiently tight.
10. Happy Feet makes "The Message" unbearably precious (2006)
Though relatively stilted, shrill, and heavy-handed by today's standards, Grandmaster Flash And The Furious Five's "The Message" holds a vaunted place in hip-hop as the first real "message" song and a milestone in socially conscious, political hip-hop. The criminally overrated jukebox musical Happy Feet perversely re-imagines Melle Mel's grim warning of the dangers and evils of inner-city life as an adorable little song for a baby penguin to sing to assert himself. Seldom has musical revisionism been this insufferably cute or utterly wrong-headed.
11. Kevin Federline releases Playing With Fire; America averts eyes, slowly walks away (2006)
Is there anything left to say about Britney's baby-daddy's ill-fated foray into hip-hop? Those last few seconds are rapidly ticking away on K-Fed's 15 minutes of utterly undeserved infamy.
12. MC Rove drops science (2007)
Having learned little from the Bush sisters' convention speech, the Republicans tried to humanize the sour-faced cauldron of evil that is Karl Rove with a queasily fascinating rap tribute at the Radio And Television Correspondents Dinner, where he was surrounded by a group of hacktastic improvisers so he could gyrate erratically and rasp "MC Rove" whenever a microphone was shoved in his face. Someone really should have told Rove that "MC" stands for "master of ceremonies," not "hateful old white man gesticulating randomly and growling two words in a bizarre, inexplicable caveman voice." Did anyone else notice that Rove's "Rapping Dance" looks suspiciously like the moves performed by the ghouls in the Thriller video? Apparently even the undead have more soul than the GOP.
13. Diddy wins something called "The Fifi Award" for Best Fragrance (2007)
If that ain't gangsta, what is?