10 Most Cringe-Worthy Rap Performances in Movies

Malibu’s Most Wanted

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Ask the head of any multibillion-dollar movie studio and they’ll tell you: That youth demographic is a tough nut to crack. With trends shifting by the hour and marketing departments only now catching up to 2012 slang, how could any middle-aged studio executive expect to keep up? And considering that every failed attempt to appeal to young adults is cruelly mocked online, these poor, innocent, out-of-touch producers are walking a tightrope simply to pander to a potentially lucrative market they couldn’t care less about. Where’s their thanks?

Nevertheless, these moviemakers soldier on and do their damndest to somehow connect with an increasingly skeptical age group. And what gimmick well have they been forced to return to for three decades? That rap music those dang kids love so much. But even with the best of intentions, it sometimes doesn’t quite work. Or to put it another way, nothing makes an audience cringe more than a terrible rapper.

With Comedy Bang! Bang! celebrating hip hop this week, turn that cap sideways and take a look at the 10 worst rap performances in movies.

10. Kid ‘N Play, Class Act

One of the few rap acts that can be identified by hair, Kid ‘N Play was, and still is, best known for their pajama-jammy-jams in the House Party franchise. But in 1992, right when gangsta rap was exploding, the duo released Class Act which featured a pro-school, anti-drug, all-embarrassing rap performance at a teen dance — punctuated by some weasley vamping from a certain Mr. Pauly Shore.

9. Mike Myers, Austin Powers in Goldmember

If the schtick hadn’t worn thin by the umpteenth time the “funny guy” at work put a pinkie to his puckered lips and hissed “One million dollarrrrs!,” then this rap from the third installment of Austin Powers certainly drove the Dr. Evil act straight into the ground. Combining the tried-and-true hilarity of white guys rapping with incessant sight gags based on dwarfism, the comedy in this sequence didn’t hold up by the time the movie hit post-production.

8. Jamie Kennedy, Malibu’s Most Wanted

By 2003, it had been a long time since Jamie Kennedy earned laughs in the Scream series when he tried to adapt his short-lived prank show’s white rapper persona to the big screen. As expected, the results failed to resonate with folks who didn’t want to feel humiliated on someone else’s behalf. But on the plus side, comments like “Dude, you’re ripping off Jamie Kennedy” helped deter many subsequent attempts of lame white rapper characters.

7. Vanilla Ice, Teenage Mutant Ninja Turtles II: The Secret of the Ooze

Arguably the biggest punchline in music history, Vanilla Ice was rocketing out of the spotlight by the time he appeared in the Teenage Mutant Ninja Turtles sequel. And as kids were also beginning to outgrow peak ninja turtle saturation, this dance fight/rap scene became a perfect storm of outdated and an early-’90s zeitgeist puzzle as to who’s dragging down who here.

6. The Leprechaun, Leprechaun: In the Hood

Four years after House of Pain’s breakup, Irish-flavored rap attempted a comeback in the form of Warwick “God, I Miss Willow” Davis dropping some science as The Leprechaun. After the mythical gold peddler is freed from imprisonment, he hits the stage backed by a Casio keyboard drum beat and uses his powers to turn the female waitstaff into booty-shaking strumpets — which, admittedly, isn’t too far off from most rap videos.

5. Neil Patrick Harris and the Smurfs, The Smurfs

Even without asking him, it’s safe to assume Neil Patrick Harris would gladly watch every awkward pubescent moment as Doogie than glance at one frame of this scene from 2011’s live-action Smurfs. Flagrantly ignoring proper Guitar Hero gameplay, Harris backs the proactive, in-your-face CGI forest creatures on Run-D.M.C.’s “Walk This Way” and proves that sometimes you shouldn’t fully commit to a role.

4. Tom Hanks and Dan Aykroyd, Dragnet

There’s not enough room in this column to get into why 1987’s Dragnet reboot didn’t work — much less get into the perils of force-feeding nostalgia onto a new generation — but the music video released alongside the movie is more awkward than a thousand Rappin’ Rodneys. Putting classic Jack Webb lines to a synth beat while stiffly dancing in unison, Hanks and Aykroyd perform a dazzling trainwreck of regrettable ideas.

3. Matthew Perry, The Ron Clark Story

The cast of Friends have their share of embarrassing movie roles, but they tend to be during the run of the series when they were young and hungry. Then there’s the made-for-TV movie The Ron Clark Story which Matthew Perry signed on for in 2006. Resurrecting the “teacher connects with urban youth” genre from the grave, Perry slips on a backwards hat and raps about the history of George Washington, winning over the exceptionally impressionable teens. (And as you watch, bear in mind, Perry was nominated for a Primetime Emmy for this role.)

2. Al “Dunkaccino” Pacino, Jack and Jill

Even though it’s presented as a tongue-in-cheek comment on celebrities shilling products for a paycheck, it’s hard to consider this scene satiric when it’s actually a celebrity shilling a product. In a movie where Adam Sandler plays mixed-gender fraternal twins, no amount of sellout commentary could distract us from how far esteemed actor Al Pacino has fallen as he raps, tap dances, and mugs into the camera. In other words, if it’s more disturbing than him hitting on Sandler as a woman, satire doesn’t matter.

1. Everyone involved in this scene from Teen Witch

And finally, we have perhaps the most gloriously misguided co-opting of black culture in any ’80s movie. Decked out in a Hawaiian shirt, a formal vest, and suspenders-with-jeans, this group of high schoolers in their 20s rap about being hot and daring the listener to “top that.” Well, with the help of her friend’s bewitching power over humiliation and trauma, a teen girl does, in fact, top that with a jaw-dropping tour de force of gawky one-upmanship.

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Weird Roles

Anthony Michael Hall’s Most Rotten Movies

Catch Anthony Michael Hall in Weird Science on Friday at 8P on IFC.

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Photo Credit: Universal/Everett Collection

Anthony Michael Hall was the quintessential ’80s nerd. We love him in classics like The Breakfast Club and National Lampoon’s Vacation. But even the brainiest among us has his weak spots. In honor of Weird Science airing this Rotten Friday, we analyze Hall’s worst movies.

Weird Science (1985) 56%

A low point for John Hughes, Weird Science is way too wacky for its own good. Anthony Michael Hall’s Gary and his pal Wyatt (Ilan Mitchell-Smith) create the “perfect woman.” Supernatural chaos ensues. The film costars a young Bill Paxton, floppy disks, and a general disconnect from all reality.

The Caveman’s Valentine (2001) 46%

This ambitious drama starring Samuel L. Jackson couldn’t live up to its rich premise. Jackson plays Romulus, a Juilliard-educated, paranoid schizophrenic who lives in a cave. Hall co-stars as Bob, a rich man, who wants to see Romulus play the piano. The plot centers around Romulus investigating a murder, but with so much going on, the movie never quite finds its rhythm.

All About the Benjamins (2002) 30%

Ice Cube plays a bounty hunter who teams up with Mike Epps’ con man to catch diamond thieves. Hall plays Lil J, a small-time drug dealer. It’s definitely a role we’ve never seen Hall in, but overall the movie isn’t funny or original enough to justify its violence.

Freddy Got Fingered (2001) 11%

This showcase for Tom Green’s goofy gross-out comedy is often hailed as one of the worst films of all time. Green plays Gord, a 20-something slacker, who dreams of having his own animated series. Hall is Dave Davidson, a CEO of an animation studio who eventually helps Gord find success. Too bad Tom Green wasn’t so lucky.

Johnny Be Good (1988) 0%

Hall plays against type as Johnny Walker, a star quarterback. Robert Downey Jr. is his best friend and Uma Thurman plays his devoted girlfriend. Despite the support of a future A-list cast, the movie lacks central conflict and charm. Or, as TV Guide put it, “Johnny be worthless.” Ouch.

Catch the “Too Rotten to Miss” Weird Science this Friday at 8P on IFC.

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Season 6: Episode 1: Pickathon

Binge Fest

Portlandia Season 6 Now Available On DVD

The perfect addition to your locally-sourced, artisanal DVD collection.

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End of summer got you feeling like:

Portlandia Toni Screaming GIF

Ease into fall with Portlandia‘s sixth season. Relive the latest exploits of Fred Armisen and Carrie Brownstein’s cast of characters, including Doug and Claire’s poignant breakup, Lance’s foray into intellectual society, and the terrifying rampage of a tsukemen Noodle Monster! Plus, guest stars The Flaming Lips, Glenn Danzig, Louis C.K., Kevin Corrigan, Zoë Kravitz, and more stop by to experience what Portlandia is all about.

Pick up a copy of the DVD today, or watch full episodes and series extras now on IFC.com and the IFC app.

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Byrning Down the House

Everything You Need to Know About the Film That Inspired “Final Transmission”

Documentary Now! pays tribute to "Stop Making Sense" this Wednesday at 10P on IFC.

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Photo Credit: Cinecom/courtesy Everett Collection

This week Documentary Now! is with the band. For everyone who’s ever wanted to be a roadie without leaving the couch, “Final Transmission” pulls back the curtain on experimental rock group Test Pattern’s final concert. Before you tune in Wednesday at 10P on IFC, plug your amp into this guide for Stop Making Sense, the acclaimed 1984 Talking Heads concert documentary.

Put on Your Dancing Shoes

Hailed as one of the best concert films ever created, director Jonathan Demme (Silence of the Lambs) captured the energy and eccentricities of a band known for pushing the limits of music and performance.

Make an Entrance

Lead singer David Byrne treats the concert like a story: He enters an empty stage with a boom box and sings the first song on the setlist solo, then welcomes the other members of the group to the stage one song at a time.

Steal the Spotlight

David Byrne Dancing
Cinecom/Everett Collection

Always a physical performer, Byrne infuses the stage and the film with contagious joy — jogging in place, dancing with lamps, and generally carrying the show’s high energy on his shoulders.

Suit Yourself

Byrne makes a splash in his “big suit,” a boxy business suit that grows with each song until he looks like a boy who raided his father’s closet. Don’t overthink it; on the DVD, the singer explains, “Music is very physical, and often the body understands it before the head.”

View from the Front Row

Stop Making Sense Band On Stage
Cinecom/Everett Collection

Demme (who also helmed 1987’s Swimming to Cambodia, the inspiration for this season’s Documentary Now! episode “Parker Gail’s Location is Everything”) films the show by putting viewers in the audience’s shoes. The camera rarely shows the crowd and never cuts to interviews or talking heads — except the ones onstage.

Let’s Get Digital

Tina Weymouth Keyboard
Cinecom/Everett Collection

Stop Making Sense isn’t just a good time — it’s also the first rock movie to be recorded entirely using digital audio techniques. The sound holds up more than 30 years later.

Out of Pocket

Talk about investing in your art: Talking Heads drummer Chris Frantz told Rolling Stone that the members of the band “basically put [their] life savings” into the movie, and they didn’t regret it.

Catch Documentary Now!’s tribute to Stop Making Sense when “Final Transmission” premieres Wednesday, October 12 at 10P on IFC.

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