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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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A-O Rewind

Celebrating Portlandia One Sketch at a Time

The final season of Portlandia approaches.

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Most people measure time in minutes, hours, days, years…At IFC, we measure it in sketches. And nothing takes us way (waaaaaay) back like Portlandia sketches. Yes, there’s a Portlandia milepost from every season that changed the way we think, behave, and pickle things. In honor of Portlandia’s 8th and final season, Subaru presents a few of our favorites.

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Put A Bird On It

Portlandia enters the pop-culture lexicon and inspires us to put birds on literally everything.

Colin the Chicken

Who’s your chicken, really? Behold the emerging locavore trend captured perfectly to the nth degree.

Dream Of The ’90s

This treatise on Portland made it clear that “the dream” was alive and well.

No You Go

We Americans spend most of our lives in cars. Fortunately, there’s a Portlandia sketch for every automotive situation.

A-O River!

We learned all our outdoor survival skills from Kath and Dave.

One More Episode

The true birth of binge watching, pre-Netflix. And what you’ll do once Season 8 premieres.

Catch up on Portlandia’s best moments before the 8th season premieres January 18th on IFC.

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WTF Films

Artfully Off

Celebrity All-Star by Sisters Weekend is available now on IFC's Comedy Crib.

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Sisters Weekend isn’t like other comedy groups. It’s filmmaking collaboration between besties Angelo Balassone, Michael Fails and Kat Tadesco, self-described lace-front addicts with great legs who write, direct, design and produce video sketches and cinematic shorts that are so surreally hilarious that they defy categorization. One such short film, Celebrity All-Star, is the newest addition to IFC’s Comedy Crib. Here’s what they had to say about it in a very personal email interview…

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IFC: How would you describe Celebrity All-Star to a fancy network executive you just met in an elevator?

Celebrity All-Star is a short film about an overworked reality TV coordinator struggling to save her one night off after the cast of C-List celebrities she wrangles gets locked out of their hotel rooms.

IFC: How would you describe Celebrity All-Star to a drunk friend of a friend you met in a bar?

Sisters Weekend: It’s this short we made for IFC where a talent coordinator named Karen babysits a bunch of weird c-list celebs who are stuck in a hotel bar. It’s everyone you hate from reality TV under one roof – and that roof leaks because it’s a 2-star hotel. There’s a magician, sexy cowboys, and a guy wearing a belt that sucks up his farts.

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IFC: What was the genesis of Celebrity All-Star?

Celebrity All-Star was born from our love of embarrassing celebrities. We love a good c-lister in need of a paycheck! We were really interested in the canned politeness people give off when forced to mingle with strangers. The backstory we created is that the cast of this reality show called “Celebrity All-Star” is in the middle of a mandatory round of “get to know each other” drinks in the hotel bar when the room keys stop working. Shows like Celebrity Ghost Hunters and of course The Surreal Life were of inspo, but we thought it
was funny to keep it really vague what kind of show they’re on, and just focus on everyone’s diva antics after the cameras stop rolling.

IFC: Every celebrity in Celebrity All-Star seems familiar. What real-life pop personalities did you look to for inspiration?

Sisters Weekend: Anyone who is trying to plug their branded merch that no one asked for. We love low-rent celebrity. We did, however, directly reference Kylie Jenner’s turd-raison lip color for our fictional teen celebutante Gibby Kyle (played by Mary Houlihan).

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IFC: Celebrity seems disgusting yet desirable. What’s your POV? Do you crave it, hate it, or both?

Sisters Weekend: A lot of people chase fame. If you’re practical, you’ll likely switch to chasing success and if you’re smart, you’ll hopefully switch to chasing happiness. But also, “We need money. We need hits. Hits bring money, money bring power, power bring fame, fame change the game,” Young Thug.

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IFC: Who are your comedy idols?

Sisters Weekend: Mike grew up renting “Monty Python” tapes from the library and staying up late to watch 2000’s SNL, Kat was super into Andy Kaufman and “Kids In The Hall” in high school, and Angelo was heavily influenced by “Strangers With Candy” and Anna Faris in the Scary Movie franchise, so, our comedy heroes mesh from all over. But, also we idolize a lot of the people we work with in NY-  Lorelei Ramirez, Erin Markey, Mary Houlihan, who are all in the film, Amy Zimmer, Ana Fabrega, Patti Harrison, Sam Taggart. Geniuses! All of Em!

IFC: What’s your favorite moment from the film?

Sisters Weekend: I mean…seeing Mary Houlihan scream at an insane Pomeranian on an iPad is pretty great.

See Sisters Weekend right now on IFC’s Comedy Crib

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Reality? Check.

Baroness For Life

Baroness von Sketch Show is available for immediate consumption.

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Baroness von Sketch Show is snowballing as people have taken note of its subtle and not-so-subtle skewering of everyday life. The New York Times, W Magazine, and Vogue have heaped on the praise, but IFC had a few more probing questions…

IFC: To varying degrees, your sketches are simply scripted examples of things that actually happen. What makes real life so messed up?

Aurora: Hubris, Ego and Selfish Desires and lack of empathy.

Carolyn: That we’re trapped together in the 3rd Dimension.

Jenn: 1. Other people 2. Other people’s problems 3. Probably something I did.

IFC: A lot of people I know have watched this show and realized, “Dear god, that’s me.” or “Dear god, that’s true.” Why do people have their blinders on?

Aurora: Because most people when you’re in the middle of a situation, you don’t have the perspective to step back and see yourself because you’re caught up in the moment. That’s the job of comedians is to step back and have a self-awareness about these things, not only saying “You’re doing this,” but also, “You’re not the only one doing this.” It’s a delicate balance of making people feel uncomfortable and comforting them at the same time.

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IFC: Unlike a lot of popular sketch comedy, your sketches often focus more on group dynamics vs iconic individual characters. Why do you think that is and why is it important?

Meredith: We consider the show to be more based around human dynamics, not so much characters. If anything we’re more attracted to the energy created by people interacting.

Jenn: So much of life is spent trying to work it out with other people, whether it’s at work, at home, trying to commute to work, or even on Facebook it’s pretty hard to escape the group.

IFC: Are there any comedians out there that you feel are just nailing it?

Aurora: I love Key and Peele. I know that their show is done and I’m in denial about it, but they are amazing because there were many times that I would imagine that Keegan Michael Key was in the scene while writing. If I could picture him saying it, I knew it would work. I also kind of have a crush on Jordan Peele and his performance in Big Mouth. Maya Rudolph also just makes everything amazing. Her puberty demon on Big Mouth is flawless. She did an ad for 7th generation tampons that my son, my husband and myself were singing around the house for weeks. If I could even get anything close to her career, I would be happy. I’m also back in love with Rick and Morty. I don’t know if I have a crush on Justin Roiland, I just really love Rick (maybe even more than Morty). I don’t have a crush on Jerry, the dad, but I have a crush on Chris Parnell because he’s so good at being Jerry.

Jenn: I LOVE ISSA RAE!

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IFC: If you could go back in time and cast yourselves in any sitcom, which would it be and how would it change?

Carolyn: I’d go back in time and cast us in The Partridge Family.  We’d make an excellent family band. We’d have a laugh, break into song and wear ruffled blouses with velvet jackets.  And of course travel to all our gigs on a Mondrian bus. I feel really confident about this choice.

Meredith: Electric Mayhem from The Muppet Show. It wouldn’t change, they were simply perfect, except… maybe a few more vaginas in the band.

Binge the entire first and second seasons of Baroness von Sketch Show now on IFC.com and the IFC app.

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