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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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Brock Hard

Brockmire’s Guide To Grabbing Life By The D***

Catch up on the full season of Brockmire now.

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“Lucy, put supper on the stove, my dear, because this ballgame is over!”

Brockmire has officially closed out its rookie season. Miss the finale episode? A handful of episodes? The whole blessed season?? You can see it all from the beginning, starting right here.

And you should get started, because every minute you spend otherwise will be a minute spent not living your best life. That’s right, there are very important life lessons that Brockmire hid in plain sight—lessons that, when applied thoughtfully, can improve every aspect of your awesome existence. Let’s dive into some sage nuggets from what we call the Book of Jim.

Life Should Be Spiked, Not Watered Down.

That’s not just a fancy metaphor. As Brockmire points out, water tastes “awful. 70% of the water is made up of that shit?” Life is short, water sucks, live like you mean it.

There Are Only Three Types of People

“Poor people, rich people and famous people. Rich people are just poor people with money, so the only worthwhile thing is being famous.” So next time your rich friends act all high and mighty, politely remind them that they’re worthless in the eyes of even the most minor celebrities.

There’s Always A Reason To Get Out Of Bed

And 99% of the time that reason is the urge to pee. It’s nature’s way of saying “seize the day.”

There’s More To Life Than Playing Games

“Baseball can’t compete with p0rnography. Nothing can.” Nothing you do or ever will do can be more important to people than p0rn. Get off your high horse.

A Little Empathy Goes A Long Way

Especially if you’ve taken someone else’s Plan B by mistake.

Our Weaknesses Can Be Our Greatest Strengths

Tyrion Lannister said something similar. Hard to tell who said it with more colorful profanity. Wise sentiments all around.

Big Things Come To Those Who Wait

When you’re looking for a sign, the universe will drop you a big one. You’re the sh*t, universe.

And Of Course…

Need more life lessons from the Book of Jim? Catch up on Brockmire on the IFC App.

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Oh Mama

Mommie May I?

Mommie Dearest Is On Repeat All Mothers Day Long On IFC

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The cult-classic movie Mommie Dearest is a game-changer. If you’ve seen it even just once (but come on, who sees it just once?), then you already know what we’re talking about.

But if you haven’t seen it, then let us break it down for you. Really quick, we promise, we’ll even list things out to spare you the reading of a paragraph:

1. It’s the 1981 biopic based on the memoir of Christina Crawford, Hollywood icon Joan Crawford’s adopted daughter.
2. Faye Dunaway plays Joan. And boy does she play her. Loud and over-reactive.
3. It was intended as a drama, but…
4. Waaaaaay over-the-top performances and bargain-basement dialogue rendered it an accidental comedy.
5. It’s a cult classic, and you’re the last person to see it.

Not sold? Don’t believe it’s going to change your life? Ok, maybe over-the-top acting isn’t your thing, or perhaps you don’t like the lingering electricity of a good primal scream, or Joan Crawford is your personal icon and you can’t bear to see her cast in such a creepy light.

But none of that matters.

What’s important is that seeing this movie gives you permission to react to minor repeat annoyances with unrestrained histrionics.

That there is a key moment. Is she crazy? Yeah. But she’s also right. Shoulder nipples are horrible, wire hangers are the worst, and yelling about it feels strangely justified. She did it, we can do it. Precedent set. You’re welcome.

So what else can we yell about? Channel your inner Joan and consider the following list offenses when choosing your next meltdown.

Improperly Hung Toilet Paper

Misplaced Apostrophes

Coldplay at Karaoke

Dad Jokes

Gluten Free Pizza

James Franco

The list of potential pedestrian grievances is actually quite daunting, but when IFC airs Mommie Dearest non-stop for a full day, you’ll have 24 bonus hours to mull it over. 24 bonus hours to nail that lunatic shriek. 24 bonus hours to remember that, really, your mom is comparatively the best.

So please, celebrate Mother’s Day with Mommie Dearest on IFC and at IFC.com. And for the love of god—NO WIRE HANGERS EVER.

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Breaking News

From Canada With Love

Baroness von Sketch Show premieres this summer on IFC.

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Breaking news that (finally) isn’t apocalyptic!

IFC announced today that it acquired acclaimed Canadian comedy series Baroness von Sketch Show, slated to make its US of A premiere this summer. And yes, it’s important to note that it’s a Canadian sketch comedy series, because Canada is currently a shining beacon of civilization in the western hemisphere, and Baroness von Sketch Show reflects that light in every way possible.

The series is fronted entirely by women, which isn’t unusual in the sketch comedy world but is quite rare in the televised sketch comedy world. Punchy, smart, and provocative, each episode of Baroness von Sketch Show touches upon outrageous-yet-relatable real world subjects in ways both unexpected and deeply satisfying: soccer moms, awkward office birthday parties, being over 40 in a gym locker room…dry shampoo…

Indiewire called it “The Best Comedy You’ve Never Seen” and The National Post said that it’s “the funniest thing on Canadian television since Kids In The Hall.” And that’s saying a lot, because Canadians are goddamn hilarious.

Get a good taste of BVSS in the following sketch, which envisions a future Global Summit run entirely by women. It’s a future we’re personally ready for.

Baroness Von Sketch Show premieres later this summer on IFC.

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