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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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The Best Of The Last

Portlandia Goes Out With A Bang

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The end is near. In mere days Portlandia wraps up its final season, and oh what a season it’s been. Lucky for you, you can watch the entire season right now right here and on the IFC app, including this free episode courtesy of Subaru.

But now, let’s take a moment to look back at some of the new classics Fred and Carrie have so thoughtfully bestowed upon us. (We’ll be looking back through tear-blurred eyes, but you do you.)

Couples Dinner

It’s not that being single sucks, it’s that you suck if you’re single.

Cancel it!

A sketch for anyone who has cancelled more appointments than they’ve kept. Which is everyone.

Forgotten America

This one’s a “Serial” killer…everything both right and wrong about true crime podcasts.

Wedding Planners

The only bad wedding is a boring wedding.

Disaster Hut

It’s only the end of the world if your doomsday kit doesn’t include rosé.

Catch up on Portlandia’s final episodes on demand and at IFC.com

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Your Portlandia Personality Test

The New Portlandia Webseries Is Going Your Way

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Carrie and Fred understand that although we have so much in common, we’re each so beautifully unique and different. To help us navigate those differences, Portlandia has found an easy and honest way to embrace our special selves in the form of a progressive new traffic system: a specific lane for every kind of driver. It’s all in honor of the show’s 8th and final season, and it’s all presented by Subaru.

Ready to find out who you really are? Match your personality to a lane and hop on the expressway to self-understanding.

Lane 10: Trucks Piled With Junk

Your junk is falling out of your trunk. Shake a tail light, people — this lane is for you.

Lane 33: Twins

You’re like a Gemini, but waaaay more pedestrian. Maybe you and a friend just wear the same outfits a lot. Who cares, it’s just twinning enough to make you feel special.

Lane 27: Broken Windows

Bad luck follows you around and everyone knows it. Your proverbial seat is always damp from proverbial rain. Is this the universe telling you to swallow your pride? Yes.

Lane 69: Filthy Cars

You’re all about convenience. Getting your car washed while you drive is a no-brainer.

Lane 43: Newly Divorced Singles

It’s been a while since you’ve driven alone, and you don’t know the rules of the road anymore. What’s too fast? What’s too slow? Are you sending the right signals? Don’t worry, the breakdown lane is nearby if you need it.

Still can’t find a lane to match your personality? Check out all the videos here. And see the final season of Portlandia this spring on IFC.

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Last-Minute Holiday Gift Guide

Hits from the '80s are on repeat all Christmas Eve and Day on IFC.

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GIFs via Giphy, Photos via The Everett Collection

It’s the final countdown to Christmas and thanks to IFC’s movie marathon all Christmas Eve and Christmas Day, you can revel in classic ’80s films AND find inspiration for your last-minute gifts. Here are our recommendations, if you need a head start:

Musical Instrument

Great analog entertainment substitute when you refuse to give your kid the Nintendo Switch they’ve been drooling over.

Breakfast In Bed

Any significant other or child would appreciate these Uncle Buck-approved flapjacks. Just make sure you’re not stuck on clean up duty.

Cocktail Supplies

You’ll need them to get through the holidays.

Dance Lessons

So you can learn to shake-shake-shake (unless you know ghosts willing to lend a hand).

Comfy Clothes

With all the holiday meals, there may be some…embigenning.



Get even more great inspiration all Christmas Eve and Day on IFC, and remember…