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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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Thank Azaria

Best. Characters. Ever.

Our favorite Hank Azaria characters.

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GIFs via Giphy

Hank Azaria may well be the most prolific voice and character actor of our time. The work he’s done for The Simpsons alone has earned him a permanent place in the pop culture zeitgeist. And now he’s bringing another character to the mainstream: a washed-up sports announcer named Jim Brockmire, in the aptly titled new series Brockmire.

We’re looking forward to it. So much so that we want to look backward, too, with a short-but-sweet retrospective of some of Azaria’s important characters. Shall we begin?

Half The Recurring Simpsons Characters

He’s Comic Book Guy. He’s Chief Wiggum. He’s Apu. He’s Cletus. He’s Snake. He’s Superintendent Chalmers. He’s the Sea Captain. He’s Kurt “Can I Borrow A Feeling” Van Houten. He’s Professor Frink. He’s Carl. And he’s many more. But most importantly he’s Moe Szyslak, the staple character Azaria has voiced since his very first audition for The Simpsons.

Oh, and He’s Frank Grimes

For all the regular Simpsons characters Azaria has played over the years, his most brilliant performance may have been a one-off: Frank Grimes, the scrappy bootstrapper who worked tirelessly all his life for honest, incremental, and easily-undermined success. Azaria’s portrayal of this character was nuanced, emotional, and simply magical.

Patches O’Houlihan

Dodgeball is a “sport of violence, exclusion and degradation.” as Hank Azaria generously points out in his brief but crucial cameo in Dodgeball. That’s sage wisdom. Try applying his “five D’s” to your life on and off the court and enjoy the results.

Harold Zoid

Of Futurama fame. The crazy uncle of Dr. Zoidberg, Harold Zoid was once a lion (or lobster) of the silver screen until Smell-o-vision forced him into retirement.

Agador

The Birdcage was significant for many reasons, and the comic genius of Hank Azaria’s character “Agador” sits somewhere towards the top of that list. If you haven’t seen this movie, shame on you.

Gargamel

Nobody else could make a live-action Gargamel possible.

Ed Cochran

From Ray Donovan. Great character, great last name [editorial note: the author of this article may be bias].

Kahmunra, The Thinker, Abe Lincoln

All in the Night At The Museum: Battle Of The Smithsonian, a file that let Azaria flex his voice acting and live-action muscles in one fell swoop.

The Blue Raja

Mystery Men has everything, including a fatal case of Smash Mouth. Azaria’s iconic superhero makes the shortlist of redeemable qualities, though.

Dr. Huff

Huff put Azaria in a leading role, and it was good. So good that there is no good gif of it. Internet? More like Inter-not.

Learn more about Hank Azaria’s newest claim to fame right here, and don’t miss the premiere of Brockmire April 5 at 10P on IFC.

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Flame Out

Brockmire and Other Public Implosions

Brockmire Premieres April 5 at 10P on IFC.

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There’s less than a month until the Brockmire premiere, and to say we’re excited would be an insulting understatement. It’s not just that it stars Hank Azaria, who can do no wrong (and yes, that’s including Mystery Men, which is only cringeworthy because of Smash Mouth). It’s that the whole backstory of the titular character, Jim Brockmire, is the stuff of legends. A one-time iconic sportscaster who won the hearts of fans and players alike, he fell from grace after an unfortunate personal event triggered a seriously public meltdown. See for yourself in the NSFW Funny or Die digital short that spawned the IFC series:

See? NSFW and spectacularly catastrophic in a way that could almost be real. Which got us thinking: What are some real-life sports fails that have nothing to do with botched athletics and everything to do with going tragically off script? The internet is a dark and dirty place, friends, but these three examples are pretty special and mostly safe for work…

Disgruntled Sports Reporter

His co-anchor went offsides and he called it like he saw it.

Jim Rome vs Jim “Not Chris” Everett

You just don’t heckle a professional athlete when you’re within striking distance. Common sense.

Carl Lewis’s National Anthem

He killed it! As in murdered. It’s dead.

To see more moments just like these, we recommend spending a day in your pajamas combing through the muckiness of the internet. But to see something that’s Brockmire-level funny without having to clear your browser history, check out the sneak peeks and extras here.

Don’t miss the premiere of Brockmire April 5 at 10P on IFC.

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Mirror, Mirror

Portlandia Season 7 In Hindsight

Portlandia Season 7 Now Available Online and on the IFC App.

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Another season of Portlandia is behind us, and oh what a season it was. We laughed. We cried. And we chuckled uncomfortably while glancing nervously around the room. Like every season before it, the latest Portlandia has held a mirror up to ridiculousness of modern American life, but more than ever that same mirror has reflected our social reality in ways that are at once hysterical and sneakily thought-provoking. Here are just a few of the issues they tackled:

Nationalism

So long, America, Portland is out! And yes, the idea of Portland seceding is still less ludicrous than building a wall.

Men’s Rights

We all saw this coming. Exit gracefully, dudes.

Protests

Whatever you stand for, stand for it together. Or with at least one other person.

Free Love

No matter who we are or how we love, deep down we all have the ability to get stalky.

Social Status

Modern self-esteem basically hinges on likes, so this isn’t really a stretch at all.

These moments are just the tip of the iceberg, and much more can be found in the full seventh season of #Portlandia, available right now #online and on the #IFC app.

via GIPHY

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