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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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SO EXCITED!!!

Reminders that the ’90s were a thing

"The Place We Live" is available for a Jessie Spano-level binge on Comedy Crib.

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Unless you stopped paying attention to the world at large in 1989, you are of course aware that the ’90s are having their pop cultural second coming. Nobody is more acutely aware of this than Dara Katz and Betsy Kenney, two comedians who met doing improv comedy and have just made their Comedy Crib debut with the hilarious ’90s TV throwback series, The Place We Live.

IFC: How would you describe “The Place We Live” to a fancy network executive you just met in an elevator?

Dara: It’s everything you loved–or loved to hate—from Melrose Place and 90210 but condensed to five minutes, funny (on purpose) and totally absurd.

IFC: How would you describe “The Place We Live” to a drunk friend of a friend you met in a bar?

Betsy: “Hey Todd, why don’t you have a sip of water. Also, I think you’ll love The Place We Live because everyone has issues…just like you, Todd.”

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IFC: When you were living through the ’90s, did you think it was television’s golden age or the pop culture apocalypse?


Betsy: I wasn’t sure I knew what it was, I just knew I loved it!


Dara: Same. Was just happy that my parents let me watch. But looking back, the ’90s honored The Teen. And for that, it’s the golden age of pop culture. 

IFC: Which ’90s shows did you mine for the series, and why?

Betsy: Melrose and 90210 for the most part. If you watch an episode of either of those shows you’ll see they’re a comedic gold mine. In one single episode, they cover serious crimes, drug problems, sex and working in a law firm and/or gallery, all while being young, hot and skinny.


Dara: And almost any series we were watching in the ’90s, Full House, Saved By the Bell, My So Called Life has very similar themes, archetypes and really stupid-intense drama. We took from a lot of places. 

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IFC: How would you describe each of the show’s characters in terms of their ’90s TV stereotype?

Dara: Autumn (Sunita Mani) is the femme fatale. Robin (Dara Katz) is the book worm (because she wears glasses). Candace (Betsy Kenney) is Corey’s twin and gives great advice and has really great hair. Corey (Casey Jost) is the boy next door/popular guy. Candace and Corey’s parents decided to live in a car so the gang can live in their house. 
Lee (Jonathan Braylock) is the jock.

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

Dara: Because everyone’s feeling major ’90s nostalgia right now, and this is that, on steroids while also being a totally new, silly thing.

Delight in the whole season of The Place We Live right now on IFC’s Comedy Crib. It’ll take you back in all the right ways.

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New Nasty

Whips, Chains and Hand Sanitizer

Turn On The Full Season Of Neurotica At IFC's Comedy Crib

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Jenny Jaffe has a lot going on: She’s writing for Disney’s upcoming Big Hero 6: The Series, developing comedy projects with pals at Devastator Press, and she’s straddling the line between S&M and OCD as the creator and star of the sexyish new series Neurotica, which has just made its debut on IFC’s Comedy Crib. Jenny gave us some extremely intimate insight into what makes Neurotica (safely) sizzle…

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

Jenny: Neurotica is about a plucky Dominatrix with OCD trying to save her small-town dungeon.

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

Jenny: Neurotica is about a plucky Dominatrix with OCD trying to save her small-town dungeon. You’re great. We should get coffee sometime. I’m not just saying that. I know other people just say that sometimes but I really feel like we’re going to be friends, you know? Here, what’s your number, I’ll call you so you can have my number!

IFC: What’s your comedy origin story?

Jenny: Since I was a kid I’ve dealt with severe OCD and anxiety. Comedy has always been one of the ways I’ve dealt with that. I honestly just want to help make people feel happy for a few minutes at a time.

IFC: What was the genesis of Neurotica?

Jenny: I’m pretty sure it was a title-first situation. I was coming up with ideas to pitch to a production company a million years ago (this isn’t hyperbole; I am VERY old) and just wrote down “Neurotica”; then it just sort of appeared fully formed. “Neurotica? Oh it’s an over-the-top romantic comedy about a Dominatrix with OCD, of course.” And that just happened to hit the buttons of everything I’m fascinated by.

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IFC: How would you describe Ivy?

Jenny: Ivy is everything I love in a comedy character – she’s tenacious, she’s confident, she’s sweet, she’s a big wonderful weirdo.

IFC: How would Ivy’s clientele describe her?

Jenny:  Open-minded, caring, excellent aim.

IFC: Why don’t more small towns have local dungeons?

Jenny: How do you know they don’t?

IFC: What are the pros and cons of joining a chain mega dungeon?

Jenny: You can use any of their locations but you’ll always forget you have a membership and in a year you’ll be like “jeez why won’t they let me just cancel?”

IFC: Mouths are gross! Why is that?

Jenny: If you had never seen a mouth before and I was like “it’s a wet flesh cave with sharp parts that lives in your face”, it would sound like Cronenberg-ian body horror. All body parts are horrifying. I’m kind of rooting for the singularity, I’d feel way better if I was just a consciousness in a cloud.

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

The-Craft

The ’90s Are Back

The '90s live again during IFC's weekend marathon.

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Photo Credit: Everett Digital, Columbia Pictures

We know what you’re thinking: “Why on Earth would anyone want to reanimate the decade that gave us Haddaway, Los Del Rio, and Smash Mouth, not to mention Crystal Pepsi?”

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Thoughts like those are normal. After all, we tend to remember lasting psychological trauma more vividly than fleeting joy. But if you dig deep, you’ll rediscover that the ’90s gave us so much to fondly revisit. Consider the four pillars of true ’90s culture.

Boy Bands

We all pretended to hate them, but watch us come alive at a karaoke bar when “I Want It That Way” comes on. Arguably more influential than Brit Pop and Grunge put together, because hello – Justin Timberlake. He’s a legitimate cultural gem.

Man-Child Movies

Adam Sandler is just behind The Simpsons in terms of his influence on humor. Somehow his man-child schtick didn’t get old until the aughts, and his success in that arena ushered in a wave of other man-child movies from fellow ’90s comedians. RIP Chris Farley (and WTF Rob Schneider).

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Teen Angst

In horror, dramas, comedies, and everything in between: Troubled teens! Getting into trouble! Who couldn’t relate to their First World problems, plaid flannels, and lose grasp of the internet?

Mainstream Nihilism

From the Coen Bros to Fincher to Tarantino, filmmakers on the verge of explosive popularity seemed interested in one thing: mind f*cking their audiences by putting characters in situations (and plot lines) beyond anyone’s control.

Feeling better about that walk down memory lane? Good. Enjoy the revival.

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And revisit some important ’90s classics all this weekend during IFC’s ’90s Marathon. Check out the full schedule here.