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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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Inauguration Alternative

Bill Murray On Repeat

It's a movie "Murray-thon" all-day Friday on IFC.

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Photo Credit: Everett Collection, GIFs courtesy of GIPHY

Democrats, Republicans and Millennials agree: 2017 is shaping up to be a spectacle — a spectacle that really kicks into high gear this Friday with the presidential inauguration. Not only will the new POTUS swear in, but all the Country’s highest offices will be filled. It’s a daunting prospect, and to feel a little anxious about it is only normal. But if your anxiety is snowballing into panic, we have a solution:
Bill Murray.

He’s the human embodiment of a mental “Happy Place”, and there’s really no problem he can’t solve. So, with that in mind, how about we all set aside reality for a moment and let Bill take the pain away by imagining a top-shelf White House cabinet filled exclusively by his signature characters. Here are a few hypothetical appointments for your consideration…

Secretary of Defense:
Bill Murray from Stripes

His incompetence is balanced by charm, and dumb luck is inexplicably on his side. America could do worse.

Secretary of State:
Bill Murray from Lost In Translation

A seasoned globetrotter steeped in regional traditions who has the respect of the whole wide world. And he kills Costello in karaoke, which is very important.

Press Secretary:
Bill Murray from Ghostbusters

“Cats and dogs, living together. Mass hysteria.” Dude knows how to brief a room.

Secretary of Health and Human Services:
Bill Murray from What About Bob.

A doctor-approved people person who knows that progress is measured in baby steps.

Secretary of Energy:
Bill Murray from Groundhog Day

Let’s be honest, this world is going to need a lot of do-overs.

Feeling better? Hold on to that bliss. And enjoy a healthy alternative to the inauguration brouhaha with multiple Murrays all Friday long in an IFC movie marathon including Kingpin, Zombieland, Ghostbusters, and Ghostbusters II.

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Home Run

Hank Azaria Gets Thrown A Curve Ball

Brockmire Premieres April 5 at 10P

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Photo Credit: Everett Collection

Unless you’ve somehow missed every episode of the Simpsons since 1989, then surely you know that Hank Azaria is one of the most important character actors of our time. He’s so prolific and his voice is so dynamic that he’s responsible for more iconic personalities than most folks realize. Basically, he’s the great and powerful Oz — except that when you pull back the curtain the truth is actually more impressive. And now Hank is coming to IFC to bring yet another character to the TV pop culture hive mind in the new series Brockmire. Check out the trailer below.

Based on the following Funny or Die short and co-starring Amanda Peet, Brockmire follows the story of imploded major league sportscaster Jim Brockmire as he tries to resurrect his career by calling plays for a floundering minor league team in a podunk town.

The series is written by Joel Church-Cooper (Undateable) and produced by Funny or Die’s Mike Farah and Joe Farrell, meaning that there’s funny in front of the camera, funny behind the camera–funny all around. Sounds like a ball to us.

Brockmire premieres April 5 at 10P on IFC.

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Car Notes

Portlandia On People Who Can’t Park

Portlandia returns tonight at 10P on IFC.

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If flagrant bad parking takes nerve, then retaliatory note writing takes neuroses. Watch Fred and Carrie take passive aggression to next level in Car Notes, the new Portlandia web series presented by Subaru. The first episode is yours right here and now, and you can see every installment of Car Notes anytime online, on the IFC app and on demand.

Portlandia returns tonight at 10P on IFC.

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