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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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Grow TFU

Adulting Like You Mean It

Commuters makes its debut on IFC's Comedy Crib.

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Jared Warner, Nick Ciavarella, and Tim Dean were once a part of Murderfist, a group of comedy writers, actors, producers, parents, and reluctant adults. Together with InstaMiniSeries’s Nikki Borges, they’re making their IFC Comedy Crib debut with the refreshingly-honest and joyfully-hilarious Commuters. The webseries follows thirtysomethings Harris and Olivia as they brave the waters of true adulthood, and it’s right on point.

Jared, Nick, Nikki and Tim were kind enough to answer a few questions about Commuters for us. Here’s a snippet of that conversation…

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IFC: How would you describe Commuters to a fancy network executive you met in an elevator?

Nick: Two 30-somethings leave the Brooklyn life behind, and move to the New Jersey suburbs in a forced attempt to “grow up.” But they soon find out they’ve got a long way to go to get to where they want to be.

IFC: How would you describe Commuters to a drunk friend of a friend you met in a bar?

Jared: It’s a show about how f*cking stupid people who think they are smart can be.

IFC: What’s your origin story? When did you all meet and how long have you been working together?

Jared: Nick, Tim, and I were all in the sketch group Murderfist since, what, like 2004? God. Anyway, Tim and Nick left the group to pursue other frivolous things, like children and careers, but we all enjoyed writing together and kept at it. We were always more interested in storytelling than sketch comedy lends itself to, which led to our webseries Jared Posts A Personal. That was a show about being in your 20s and embracing the chaos of being young in the city. Commuters is the counterpoint, i guess. Our director Adam worked at Borders (~THE PAST!!~) with Tim, came out to a Murderfist show once, and we’ve kept him imprisoned ever since.

IFC: What was the genesis of Commuters?

Tim: Jared had an idea for a series about the more realistic, less romantic aspects of being in a serious relationship.  I moved out of the city to the suburbs and Nick got engaged out in LA.   We sort of combined all of those facets and Commuters was the end result.

IFC: How would Harris describe Olivia?

Jared: Olivia is the smartest, coolest, hottest person in the world, and Harris can’t believe he gets to be with her, even though she does overreact to everything and has no chill. Like seriously, ease up. It doesn’t always have to be ‘a thing.’

IFC: How would Olivia describe Harris?

Nikki:  Harris is smart, confident with a dry sense of humor but he’s also kind of a major chicken shit…. Kind of like if Han Solo and Barney Rubble had a baby.

IFC: Why do you think the world is ready for this series?

Nikki:  I think this is the most accurate portrayal of what a modern relationship looks like. Expectations for what your life is ‘supposed to look like’ are confusing and often a let down but when you’re married to your best friend, it’s going to be ok because you will always find a way to make each other laugh.

IFC: Is the exciting life of NYC twentysomethings a sweet dream from which we all must awake, or is it a nightmare that we don’t realize is happening until it’s over?

Tim: Now that i’ve spent time living in the suburbs, helping to raise a two year old, y’all city folk have no fucking clue how great you’ve got it.

Nikki: I think of it similar to how I think about college. There’s a time and age for it to be glorious but no one wants to hang out with that 7th year senior. Luckily, NYC is so multifaceted that you can still have an exciting life here but it doesn’t have to be just what the twentysomethings are doing (thank god).

Jared: New York City is a garbage fire.

See the whole season of Commuters right now on IFC’s Comedy Crib.

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C'mon Fellas

A Man Mansplains To Men

Why Baroness von Sketch Show is a must-see.

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Mansplaining is when a man takes it upon himself to explain something to a woman that she already knows. It happens a lot, but it’s not going to happen here. Ladies, go ahead and skip to the end of this post to watch a free episode of IFC’s latest addition, Baroness von Sketch Show.

However, if you’re a man, you might actually benefit from a good mansplanation. So take a knee, lean in, and absorb the following wisdom.

No Dicks

Baroness von Sketch Show is made entirely by women, therefore this show isn’t focused on men. Can you believe it? I know what you’re thinking: how will we know when to laugh if the jokes aren’t viewed through the dusty lens of the patriarchy? Where are the thinly veiled penis jokes? Am I a bad person? In order: you will, nowhere, and yes.

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Huge Balls

Did you know that there’s more to life than poop jokes, sex jokes, body part jokes? I mean, those things are all really good things, natch, and totally edgy. But Baroness von Sketch Show does something even edgier. It holds up a brutal funhouse mirror to our everyday life. This is a bulls**t world we made, fellas.

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Oh Canada

After you watch the Canadian powerhouses of Baroness von Sketch Show and think to yourself “Dear god, this is so real” and “I’ve gotta talk about this,” do yourself a favor and think a-boot your options: Refrain from sharing your sage wisdom with any woman anywhere (believe us, she gets it). Instead, tell a fellow bro and get the mansplaining out of your system while also spreading the word about a great show.

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Dudes, that’s the deal.
Women, start reading again here:


Check out the preview episode of Baroness von Sketch Show and watch the series premiere August 2 on IFC.

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Happy Tears

Binge Don’t Cringe

Catch up on episodes of Documentary Now! and Portlandia.

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Photo Credit: GIFs via GIPHY

A brain can only take so much.

Every five minutes, all day, every day, ludicrously stressful headlines push our mental limits as we struggle to adapt to a reality that seems increasingly less real. What’s a mind to do when simple denial just isn’t good enough anymore?

Radical suggestion: repeal and replace. And by that we mean take all the bad news that keeps you up at night, press pause, and substitute it with some genuine (not nervous, for a change) laughter. Here are some of the issues on our mind.

Gender Inequality

Feminist bookstore owners by day, still feminist bookstore owners by night, Toni and Candace show the male gaze who’s boss. Learn about their origin story (SPOILER: there’s an epic dance battle) and see what happens when their own brand of empowerment gets out of hand.

Healthcare

From Candace’s heart attack to the rise of the rawvolution, this Portlandia episode proves that healthcare is vital.

Peaceful Protests

Too many online petitions, too little time? Get WOKE with Fred and Carrie when they learn how to protest.

What Could Have Been

Can’t say the name “Clinton” without bursting into tears? Documentary Now!’s masterfully political “The Bunker” sheds a cozy new light on the house that Bill and Hill built. Just pretend you don’t know how the story really ends.

Fake News

A healthy way to break the high-drama news cycle is to switch over to “Dronez”, which has all the thrills of ubiquitous adventure journalism without any of the customary depression.

The more you watch, the better you feel. So get started on past episodes of Documentary Now! and Portlandia right now at IFC.com and the IFC app.

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