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From ‘Shaun’ to ‘Superbad': The 10 Best R-Rated Comedies of the Past 10 Years

22 jump street

If filmmakers Phil Lord and Christopher Miller have a bad movie in them, we have yet to see it.

Their sequel 22 Jump Street, starring Jonah Hill and Channing Tatum, has grossed nearly $200 million worldwide since its opening on June 13, ensuring that more R-rated comedies will be coming soon to a theater near you.

Hot off Jump Street’s impressive performance – it scored the second-biggest opening ever for an R-rated comedy – let’s look back at the 10 best comedies of the past decade for the 17-and-up crowd.

Wedding Crashers

10. ‘The Wedding Crashers’

Vince Vaughn and Owen Wilson tried to replicate the success of this 2005 hit with The Internship, and came up short. Thankfully, that misfire didn’t taint Crashers’ brand of comedy, which still holds up nearly 10 years later.


9. ‘Ted’

Seth MacFarlane takes a seemingly one-joke premise – the misadventures of a foul-mouthed teddy bear and his best friend, played by Mark Wahlberg – and surprisingly gets a lot of comedic mileage out of it. Less a reliance on Family Guy-style cutaway gags and more a sharp, occasionally heartfelt, buddy comedy with real stakes, Ted earns more laughs than not on its way to becoming a movie worth repeat viewings.


8. ‘The Hangover’

Unlike most of the films on this list, the 2009 comedy hit hasn’t aged as well. While a lot of the humor is seemingly derived from characters shouting variations of “What the hell?!” after something ridiculous happens, the lead trio — Bradley Cooper, Zach Galifianakis and Ed Helms – yields laugh-out-loud results. Their chemistry and comedic timing are still major factors to the film’s success.


7. ‘Tropic Thunder’

Ben Stiller directs and co-stars in this inspired 2008 satire about a group of actors making a Vietnam movie who suddenly find themselves engaged in real-life combat. Standouts include scene-stealer Tom Cruise as an F word-fueled movie exec and Robert Downey Jr.’s Kirk Lazarus, a five-time Oscar-winning Method actor who hilariously teaches us the dangers of going “Full retard.”


6. ’21 Jump Street’/’This Is the End’ (Tied)

Picking between these two film is a Sophie’s Choice. Don’t make us do it.

A summer 2013 sleeper hit, This is the End is an Apatow School of Comedy reunion, as vets Seth Rogen and James Franco headline an ensemble that finds everyone from Jonah Hill to Danny McBride as our last hope to save the world from the apocalypse. 21 Jump Street, meanwhile, establishes the superpower directors Lord and Miller possess: Take a seemingly not-good idea – a movie based on a cheesy TV show about undercover cops posing as teens – and turn it into something that’s swing-for-the-fences great.


5. ‘Superbad’

Jonah Hill’s potential gets elevated to leading-man status in this 2007 high-school comedy written by Seth Rogen and Evan Goldberg. A perfectly understated Michael Sera co-stars in the film, which hits a perfect balance between low-brow sight gags (a notebook full of increasingly funny penis doodles) and inspired, Apatow-y quips. Also: McLovin’.


4. ‘Team America: World Police’

If you haven’t seen this movie yet, how do you live? Seriously, you’re some type of wrong person. South Park’s Trey Parker and Matt Stone hilariously skewer Bruckheimer-sized action epics, Hollywood and politics with the help of instantly quotable, foul-mouthed puppets. Watch the unrated cut. At least eleventy times.


3. ‘Knocked Up’

Judd Apatow’s 2007 follow-up to The 40-Year-Old Virgin furthers the writer-director’s signature blend of unflinching comedy and genuine drama, as Seth Rogen stars as a 30-something slacker forced to grow up when one-night stand Katherine tells him she’s pregnant. Very smart, very hilarious comedy ensues; one of Apatow’s best. (Bonus points for introducing us to Jonah Hill.)


2. ‘Shaun of the Dead’

As funny as it is scary, Edgar Wright’s feature film debut effortlessly straddles the fine line between horror and comedy – delivering one of the past decade’s most accomplished films. As the undead swarm London, Simon Pegg and Nick Frost struggle to keep a small group safe inside a local pub as zombie hordes threaten to turn them into dinner. Endlessly inventive action scenes, in concernt with a few truly gripping emotional beats, make Shaun one of the best entries in the genre.


1. ‘The 40-Year-Old Virgin’

Writer-director Judd Apatow’s feature debut is “Patient Zero” for the current crop of films infecting us with laughter. It launched big-screen careers for Steve Carrell and Seth Rogen, as well as a successful brand of R-rated humor in one of the best comedies – “R” or otherwise – ever made.


  • JALexander

    Wait a minute…Ted over Bridesmaids???

  • Andrew

    Very surprised Borat isn’t on this list. Hangover wasn’t very funny the first time. Or the second time. Or at all. I think Borat should replace that one. Otherwise, great list!

  • Chub Nutt

    Pineapple Express?

  • ggny

    Really didnt think Ted was that funny. I would put Bridesmaids,Adventureland,She’s Out of my League all before that. Also when is the cut off date? Harold and Kumar came out in the end of July 2004 and there is no reason that shouldnt be on the list

  • Rocky Rhodes

    Decent article (tho a bit too much Apatow Ass-Suckage). Virgin over Shaun is arguable (at least to me). My biggest complaint: where’s Paul?!?!?

  • Kaine Morrison

    Where is Hot Tub Time Machine????
    That was amazing!!!!
    It really felt like an 80’s comedy. And it didn’t get bogged down in the middle with some crappy drama. It stayed hilarious throughout!

  • Yakushiji Tenzen

    Any movie by Adam McKay I’d say. For tv I’d say my favorite comedy of all time that I can watch over and over is Always Sunny in Philadelphia. The gang never fail to make me laugh.

  • Greg N

    where is Bridesmaids and Black Dynamite?! they blow these all out of the water, Shaun is the only one on this list that I think is a comedy that stands the test of time.

  • Peter Whitney

    Most of those films are ok, but don’t really hold up to multiple viewings. I defnitely agree that Shaun and Tropic belong on there. And I agree that Borat should be on that list. To be fair though, I am hard pressed to think of ten great R rated comedies from the last ten years.

  • Viktor Åkesson

    21 Jump Street had an offensive remark towards autism, and The 40-Year-Old Virgin has an offensive joke about trans people AND further makes it clear guys should be ashamed of being virgins as if sex is the only important thing with love…

    … Phil Pirrello, go and fuck yourself.

  • Gary

    I may be off the mark, but I sense that you are an Autistic transexual virgin.

  • Garrett

    No, I think you pretty much nailed it.

  • James

    Bridesmaids is a lot funniest than majority on this list. The plane scene is my personal favourite.

  • James

    Such a shit movie.

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  • Wellman

    No love for Hot Fuzz or Black Dynamite? This must be based off of Box Office and not actual quality right?

  • John

    WHERE IS STEP BROTHERS!!!??? So quotable and hilarious

  • Gregg Brennan

    In a sewer somewhere with all the rest of the crap. That movie was terrible.

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  • JohnB

    I Love you, Man….Role Models…Borat…Talladega Nights…

  • John Pannozzi

    Am I the only one who kinda wanted to see Clerks II on there?

  • Jacob Hammer

    Didn’t like Tropic Thunder or the 40 year old virgin.

  • Jacob Hammer

    Role Models, totally agree. Really under rated. Paul Rudd always delivers.