A Brief History of White People Rapping in Movies

In the new A-list-heavy flick The Place Beyond the Pines, all signs point to prestige. Behind the camera, writer-director Derek Cianfrance is coming off of 2010's Blue Valentine, a critical darling that solidified star Ryan Gosling's industry clout and earned Michelle Williams an Academy Award nomination for Best Actress. In front of the camera, Pines co-star Gosling is joined by recent Oscar nominee Bradley Cooper, and story wise, it's an ambitious three-part drama that'd scream "Awards bait!" is this were, say, November or December.

Throughout The Place Beyond the Pines, Cianfrance goes out of his way to achieve credibility—so what's up with the random moment of white-boy rap that happens during its third act? When co-star Emory Cohen busts a few unfortunate rhymes, Cianfrance's film immediately joins the ranks of other motion pictures, both good and bad, that have, whether intentionally or not, tapped into that universal truth: The sight of white folks rapping will always cause a double take.

Of course, talented lyricists like Eminem have been able to defy the odds, but Dan Aykroyd and Topher Grace? Not so much. For an overview of this often embarrassing phenomenon, have a look at this brief history of white people rapping in movies. And just hope that your melanin-free skin is also thick.

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Written by Tara Aquino (@t_akino), Matt Barone (@MBarone), and Ross Scarano (@RossScarano)

Song: "City of Crime"
Level Of Embarrassment: Medium

Most Americans would say that, "No, there isn't anything that Tom Hanks can't do." But have those people heard Tom Hanks rap over the end credits of Dragnet? Pysche! Tom Hanks is a fucking fantastic rapper! He brings extra-large personality to his bars on "City of Crime," shouting his raps like he just watched a Beastie Boys video once. Aykroyd plays it straight, almost like he's doing solemn spoken word. The combination makes for an experience that's more quaint than offensive. —RS

Song: "Top That" by Larry Weir
Level Of Embarrassment: Extremely High

Why would we ever really wanna top that? We can't. There is no better musical scene in a film. Ever. If there's one scene to show your children to encapsulate the late '80s, please choose this one, in which the little Jewish girl finds her voice through a witch's spell and becomes able to rap.

But it wasn't just a perfect portrait of the decade, Teen Witch taught us to never sell ourselves short. When the white girl saw her crush violently thrusting at his two guy friends and aggressively rapping, before discover her own lyricism, she says, "Look how funky he is. I will never be hip." She had a really low threshold for funky, we guess. —TA

Song: "Ninja Rap"
Level Of Embarrassment: Extremely High

Perhaps because MC Hammer was too busy writing "Addams Groove" for The Addams Family, the producers of 1991's Teenage Mutant Ninja Turtles sequel attempted to tap into the hip-hop culture zeitgeist by having Vanilla Ice pen an original song, "Ninja Rap," and perform it during the film's camp-tastic centerpiece. What, it's not like they were going to call Partners in Kryme again.

Experienced by TMNT-obsessed kids back in '91, the scene was a great marriage between their favorite reptilian superheroes and the dude responsible for "Ice, Ice Baby"; revisited today, however, it's a wonderfully silly congregationof bad dance moves, awful music, and overly colorful early '90s fashion.

That's right, Vanilla Ice just so happens to be rapping about ninjas at the same time that four karate-chopping turtles join the crowd and pummel one of Shredder's underlings with their shells. Which gives them enough time to hop on stage and make the Ice man look like Chris Brown as they boogie on down before Shredder crashes the party. —MB

Song: N/A (Freestyle)
Level Of Embarrassment: Not Embarrassing

It seems like a recipe for shameful embarrassment: a white dude with dreads, wearing pajamas, speed-rapping like he's the third member of Das EFX in front of a crowd full of non-white peers. And had Kid 'n Play cast, say, David Faustino to play Jamal in House Party 2, that would've undoubtedly been the result. Fortunately, the fun-loving rap duo reached out a real-life MC for the role: Kamron (no Giles), one-fifth of the short-lived, all-white, and ironically named group Young Black Teenagers. Co-signed by Public Enemy, YBT weren't half bad, as evidenced by their underrated 1993 single "Tap the Bottle." Prefacing that track by two years, Kamron handles himself nicely in House Party 2.

Fun fact: Das EFX's debut LP, Dead Serious, didn't come out until 1992—could they have seen House Party 2 and caught some inspiration from Mr. Kamron? Probably not, but stranger things have happened. —MB

Song: "Big Money Rap"
Level Of Embarrassment: Extremely High

Everything about this scene is designed to cause discomfort. When Warren Beatty's Senator Jay Bullington Bulworth decides to ditch the script to speak about the problems of special interest groups and the awful influence of money in American politics, he sets everyone on edge—including viewers. But it's not the content that grates; it's the form.

He raps. All the buttoned-up white folks in the audience look aghast. Two black women come to his aid and act as backup vocalists. From the film's POV, progressives viewers are supposed to feel good about the truth Bulworth spits. But if you respect rap, you have to cringe at the film's ham-fisted use of the music and culture. Also, who dressed Halle Berry in a jockstrap? —RS

Song: "Rapper's Delight" by The Sugarhill Gang
Level Of Embarrassment: Kind of awesome, actually

Oh, your grandma's cool? Sorry if we steal the "Coolest Grandma" mug from her cabinet and give it to someone more deserving: Ellen Albertini Dow. She's the only one who has earned that mug, buddy. She looks like she's four-foot-nothing and just a step away from a shattered hip, but that doesn't mean she doesn't know hip-hop, know what we're sayin'?

She only sings a little of the longest song in history, "Rapper's Delight," in a wedding reception scene in The Wedding Singer, but anytime we hear that song, we still picture that little granny's joy in performing it for a crowd. Pretty adorable stuff. —TA

Song: N/A (Freestyle)
Level Of Embarrassment: Extremely High

Depending on how you look at it, Whiteboyz is either a scathing satire about how middle- to upper-class Caucasians are easily swayed by the rap lifestyle or a spot-on, hilarious look at that subject. Our interpretation: It's both, though mostly the latter.

It's the ultimate wannabe-gangster story: Flip Dog, Trey Dog, and Jay Dog are three well-off teenagers living in Holyoke, Iowa, who fancy themselves as "down" hip-hop heads and desperately want to be black. Whenever they're not air-rapping along with music videos, or working dead-end fast food jobs, they're holding awkwardly imposing and horribly lyrical freestyle ciphers in Flip's basement bedroom.

Flip, who's the most serious about becoming a rap superstar, carries himself like former Hypnotized Minds' associate Lil Wyte, not Eminem. It's too bad that he's barely even Milkbone on the mic. —MB

Song: "No Tears" by Scarface
Level Of Embarrassment: High

Regardless of race, we've all been there. That moment when, whether it's work-related or your girlfriend just broke up with you, the need to let off some steam leads an angry dude to channel his inner demons through some aggressive, profanity-laden gangster rap. Unlike Office Space's tragically named, nerdy honky Michael Bolton (David Herman), though, most of us are smart enough to keep those karaoke sessions indoors. You know, without any company.

Feeling all kinds of gully thanks to Scarface's "No Tears," Michael, who's stuck in a serious traffic jam, busts out some of Face Mob's hardest rhymes ("I won't stop until I see your monkey-ass drop"). That is, until a black dude walks by his car selling flowers, which causes Michael to remember that he's a corny, pasty, shook white dude, lower the music, and lock his door. Remember, corporate gangsters don't dance—they bitch out. —MB

Song: N/A (Convenience Store Freestyle)
Level Of Embarrassment: Eh, not that embarrassing (and for the very important reason discussed below)

In Jay and Silent Bob Strike Back, a short scene depicts the evolution of the title characters from tiny infants loitering outside a convenience store to fully grown men loitering outside a convenience store. A rap song functions as a sound bridge between the shots. Jay reels off a quick rap, obviously as a joke, but—and this distinction is the most important distinction to make when discussing white people rapping—it's a joke because of the rhymes, not a joke about the inherent funniness of a white person rapping. The former is fine; the latter is pathetic and outdated. —RS

Song: N/A (Self-written battle raps)
Level Of Embarrassment: Actually, this one's 10 times better than most other rapping scenes in movie history

Leave it to G.O.A.T. nominee Eminem to give white rap fans something to be proud of on the big screen. Whereas the rest of the vanilla actors in this countdown make self-respecting Caucasians cringe from embarrassment, Marshall Mathers' loosely biographical character, B-Rabbit, in the empowering 2002 drama 8 Mile gives those same viewers reasons to cheer long before he grabs a microphone.

His mother is a mess, his little sister is often left alone inside their crappy trailer, and his girl sleeps with another dude—rather than go postal, though, Sir Rabbit retaliates against his many oppressors the only way he knows how to: coming off the dome to verbally annihilate the non-white MCs who laughed at him every step of the way prior to their lyrical assassinations. Which is precisely what Eminem himself did before "My Name Is..." exploded onto MTV's Total Request Live back in 1999. That's keeping it real. —MB

Song: N/A (Battle Freestyle)
Level Of Embarrassment: High

"I may be white, but inside my soul is black as night." So begins Brad Gluckman's (Jamie Kennedy) battle freestyle in Malibu's Most Wanted. Gluckman is the son of a Senator, and identifies in superficial ways with rap culture. He becomes a cartoon of a white wannabe, and this battle is his lowest moment. He punctuates his final bars with the n-word, and is dragged from the establishment kicking and screaming like a scared and confused child.

The scene is mostly embarrassing because Jamie Kennedy (who has a credit on the screenplay) thinks he's provocatively skewering race and privilege, when he's really just hammering away at leaden ideas with fists of ham. —RS

Song: "Get Ur Freak On" by Missy "Misdemeanor" Elliott
Level Of Embarrassment: Extremely High

One of the greatest comedic scenes in recent history is an intoxicated Leslie Mann trying to encourage the completely sober, and virginal, Steve Carell to enjoy Missy Elliott as much as she is while driving erratically (and drunk). Mann masterfully portrays the wasted suburbanite who thinks she looks really cool when she raps. Which sounds like a tweet taken straight out of the @WhiteGrlProblem Twitter feed. —TA

Song: "Straight Outta Compton" by N.W.A.
Level Of Embarrassment: High

When you think of Topher Grace and Dan Fogler, the word "cool" doesn't exactly come to mind, let alone "hip hop." So those guys lip syncing to "Straight Outta Compton" in an '80s-set teen comedy probably sounds like a joke. But it's not, and it's exactly what they do after we watch their characters steal a car just to impress a girl they knew in high school. Hey, we get it, they're hyped on life and feel like badasses. It's embarrassing, yeah, but it's only natural for them to express that fleeting badassery somehow. Kind of like the reason why you sing Journey's "Don't Stop Believing" when you're drunk. —TA

Song: "Jump" by Kris Kross
Level Of Embarrassment: Meh

Timberlake has a lot of street cred, which was not something that looked likely when he was the ramen-headed boy in N*SYNC. He built up his reputation, earned his platinum records, and now gets to sing alongside greats like Jay-Z. That's why you have to respect the man for risking it all by rapping along to Kris Kross' "Jump" in the rom-com, Friends With Benefits. It's not pretty—he's in a robe, jumps enthusiastically along, and admits to dressing like the duo, who wore their clothes backwards, for three Halloweens in a row. But Timberlake is an unstoppable force. We're pretty sure at this point in his career he could actually bring back the backwards clothes and people would jump on that shit like it's a suit and tie. —TA

Song: "No Diggity" by Blackstreet
Level Of Embarrassment: Medium embarrassing, until she sings and then you're like, "Holy shit, never mind."

Pitch Perfect is a hilarious story of an underdog team in an unexpected world, and the hero of the group is none other than Broadway baby Anna Kendrick. Also unexpected? That the Academy Award and Tony Award nominee, Kendrick, can rap Blackstreet like she's been singing it in the car since middle school. It's like she genuinely surprises herself when it bubbles up from inside of her—it's the core of her being. "No Diggity" is within her soul, man. The rest of her teammates, and the crowd at the riff-off they're competing in, are left to wonder, "What the hell was that?" while she slowly encourages her band of misfits to join in. —TA

Song: "Hanging with Da Dopeboys" by Dangeruss
Level Of Embarrassment: Spring Breakers laughs at the idea of embarassment

Making his entrance in Harmony Korine's film as dancing piece of candy Spring Breakers, Alien (played by James Franco with extra relish) is first scene performing "Hangin With Da Dopeboys" by Dangeruss, the rapper who Franco shadowed as prep for the role. It's awesome. He then talks about how St. Pete during spring break is a special ethereal moment. A place, in fact, that we've all been transported to.

He's not lying. Spring Breakers is an experience and a journey. Hold on to your butts. —RS

Song: N/A (Inside a Tunnel With a New Friend Freestyle)
Level Of Embarrassment: High

Spoiler alert! You will not like AJ, the son of Bradley Cooper's character in The Place Beyond the Pines. Most viewers won't even know they're going to meet AJ when Derek Cianfrance's inert epic begins. And yet here is AJ, a high-school aged kid who affects a rapper's swagger. He spits out his words from his babyfat face like a Jersey Shore Brando. And then, he raps. A freestyle, he claims. His braggadocio wafts from his wife beater like a spritz of Axe deodorant. You won't like AJ, and that's the point. —RS