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The 25 Funniest Movies Ever... This Millennium

Anchorman
DreamWorks

Everyone has their own personal favorite genre, but comedy is arguably the most universal. Have you ever met someone who's said, "I don't like to laugh"? Neither have we.

The past decade has seen filmmakers like Adam McKay and Judd Apatow rise from obscurity onto the A-list, while actors like Seth Rogen and Zach Galifianakis have gone from esoteric television shows to big-budget movies.

But enough talk. Read. Argue. Yell at us. You can debate the order of these films all you want, but you can't deny the humor of any of them.

25. 'Meet the Parents' (2000)

Meet the Parents
Universal

If one of the benchmarks of good comedy is making the personal universal and the universal personal, it's easy to see why Jay Roach's "Meet the Parents" was so successful upon its release. What couple hasn't dreaded the initial meeting between the boyfriend and his girl's parents? Think back to that awkward attempt to be on your best behavior; that terrifying internal fear of saying something stupid or, worse, accidentally offensive. Now double it if the steely gaze of Robert De Niro, in his best comedic performance since 1988's "Midnight Run," is the guy you’re trying to impress.

24. 'Napoleon Dynamite' (2004)

Napoleon Dynamite
Fox Searchlight

Every year or two, a small comedy breaks through the indie ceiling and into quasi-mainstream acceptance. The plot for this one couldn't be simpler: frustrated nerd growing up in small-town Idaho hates high school and virtually everyone in town. But screenwriter and director Jared Hess imbued every character – the cloying older brother Kip Chip, the adventurous grandma, the naïve, but good-natured friend Pedro, the pathetic Al Bundy arrogance of Uncle Rico – with innate warmth that celebrated rather than mocked the group’s small-town demeanor. And we'll make you an editor here if you can find us a better dance scene. (Ed. Note: We won’t really.)

23. 'Easy A' (2010)

Easy A
Sony

The "high school angst" comedy has been done to death, most notably in the iconic films of John Hughes ("The Breakfast Club," "Sixteen Candles.") So why does Will Gluck's modern retelling of "The Scarlet Letter" make the list? Thank Emma Stone's mature-beyond-her-years performance and Bert Royal's script, which, unlike "Juno," actually sounded realistic when spoken by high schoolers. Add Stanley Tucci and Patricia Clarkson as the coolest parents ever and it's a done deal.

22. 'Black Dynamite' (2009)

Black Dynamite
Sony Classics

Fans of 1970s blaxploitation films will appreciate this one the most, but even if you don't know your Truck Turner from your Cleopatra Jones, Scott Sanders and Michael Jai White's dead-on spoof of the genre accomplished a rare feat for a satire: nailing the intended targets while functioning as a fun, well-made movie in its own right. White perfectly walks the line between earnest adherence to the genre and tongue-in-cheek playfulness.

21. 'Pineapple Express' (2008)

Pineapple Express
Sony

Billed as the first "stoner action comedy," the lead roles were originally cast with Seth Rogen as the laid back drug dealer and James Franco as the user who accidentally witnesses a murder by a rogue cop and drug kingpin. Sure, that makes more sense, but flipping the roles ended up a jarringly good idea, combining the good-natured, what-planet-are-we-on humor of Cheech and Chong with grenades, guns and explosions. The cast, which included "Your Highness" star Danny McBride, improvised some of the film's funniest lines, proof that off-screen camaraderie breeds the best on-screen humor.

20. 'Step Brothers' (2008)

Step Brothers
Sony

Director Adam McKay and stars Will Ferrell and John C. Reilly reunite after the success of 2006's "Talladega Nights" in this slapstick film about two unemployed, emotionally stunted, middle-aged men whose single parents marry and force them to live with each other. More than a little friction, as expected, occurs. "Step Brothers" isn't the smartest comedy on the list, but when you tell Ferrell and Reilly to just act like children, it's hard to argue with the results.

19. 'Bad Santa' (2003)

Bad Santa
Miramax

The surliest, most foul-mouthed character on our list, Willie T. Stokes is an alcoholic, boorish, misanthropic, misogynistic lout, a.k.a. the type of person you would actually expect to play Santa at your local department store in real life. It didn't hurt that Billy Bob Thornton's demeanor comes off a bit gruff and dismissive in real life, but the sheer number and creativity of screenwriters Glenn Ficarra and John Requa's one-liners – "I loved a woman who wasn't clean," says Stokes to a child asking about his hair loss – justifies repeated viewings.

18. 'Harold and Kumar Go to White Castle' (2004)

Harold and Kumar Go to White Castle
New Line

We'll let the blatant product placement slide if a comedy is as funny as this stoner film about two twentysomethings on a simple, drug-fueled quest to find the titular fast-food franchise. The journey from A to B naturally has about 438 roadblocks – as often happens when drugs are involved – but Kal Penn and John Cho keep things light with hysterical, pseudo-philosophical musings. If you haven't seen it, expect some surprising cameos as well.

17. 'Super Troopers' (2001)

Super Troopers
Fox Searchlight

Two years before "Reno 911!" began spoofing "COPS" and its progeny, comedy troupe Broken Lizard was sending up state troopers in this high-energy comedy. Somewhere in Vermont – where the biggest crime is killing time – four state troopers are in danger of losing their jobs thanks to state budget cuts. Eager to please their superiors, the group embarks on an investigation of high-profile marijuana dealers, but have to stave off a rival police force first. Lazy, stoned cops always make for good comedy.

16. 'The Other Guys' (2010)

The Other Guys
Sony

Will Ferrell practically owns this list, and for this 2010 film, teamed up with Mr. Comedy himself Mark Wahlberg to star as two cops – well, one cop and one forensic accountant – in their take on the not-so-buddy cop movie. Ferrell, of course, has his nerd role down perfectly, yet Wahlberg, best known for dramas such as "Boogie Nights," "The Departed" and "The Fighter," uses his rough demeanor as the perfect comedic foil to Ferrell's sheepish detective.

15. 'Road Trip' (2000)

Road Trip
Dreamworks

Like the teen comedy genre, we've seen the road trip movie handled by everyone from Dennis Hopper to Vincent Gallo. But Todd Phillips ratcheted up the gross-out factor to create one of the decade’s most indelible and, in its own way, heartfelt looks at college and being away from home. Ostensibly a story about a guy who travels from New York to Texas to prevent his long-distance girlfriend from seeing an incriminating videotape, the plot is merely a backdrop for raucous frat parties, exploding cars, stoned canines and mice eating. Ah, college.

14. 'Mean Girls' (2004)

Mean Girls
Paramount

It's funny how "Saturday Night Live" projects are always funnier when they're not based on one of the show's characters ("Wayne's World" nothwithstanding). Tina Fey's script about a social outcast (Lindsay Lohan, in her best role) who befriends and eventually detracts from the "rich clique" both memorializes and sends up the typical female high school experience. Produced by "SNL" honcho Lorne Michaels, the film features "SNL" alum Amy Poehler, Ana Gasteyer and Tim Meadows in supporting roles, and Rachel McAdams and Amanda Seyfried in their first high-profile roles.

13. 'Superbad' (2007)

Superbad
Sony

If the central criticism surrounding the Judd Apatow universe is a penchant for maudlin sentimentality following hilarious bouts of immaturity and arrested development, Greg Mottola’s "Superbad" focuses strictly on the latter. Seth Rogen and Evan Goldberg started writing the film's script when they were 13; precocious for screenwriters, but the perfect age to document the angst and awkwardness of two teenage boys. And as McLovin, the hopelessly misdirected friend, Christopher Mintz-Plasse set the new bar for brilliant sidekicks.

12. 'Forgetting Sarah Marshall' (2008)

Forgetting Sarah Marshall
Universal

Before Russell Brand was a household name in the US, he was Aldous Snow, a drugged-out rock and roller – big stretch, Russ – who steals the titular character (Kristen Bell) from Jason Segel. While the cast, including Mila Kunis, Jonah Hill and Bill Hader, clearly relish the Hawaiian setting, in retrospect, this is Brand's film, as the mercurial actor swallows the scenery and owns every scene he's in. Oh, and you get to see Jason Segel's penis if you’re into that sort of thing. (The film's spin-off, "Get Him to the Greek," has to be considered a runnerup on this list.)

11. 'Wedding Crashers' (2005)

Wedding Crashers
New Line

In real life, repeatedly sneaking into weddings to meet women will probably get your ass handed to you, but you're not as slick as Vince Vaughn and Owen Wilson. As divorce mediators, the pair is understandably a bit cynical about marriage, so, ironically, they hit up weddings on the weekends for the free food, booze and, hopefully, women. When Wilson falls for the sister of one of the brides, well, you can see where this one's going. As the violent sociopath and boyfriend of Wilson's love, Bradley Cooper's breakthrough performance as Sack may be the most underrated of the decade.

10. 'Knocked Up' (2007)

Knocked Up
Universal

Okay, so maybe it's not 100 percent plausible that after having an one-night stand, Seth Rogen and Katherine Heigl would decide to stay friendly and work their way through Heigl's pregnancy together. But Judd Apatow's sophomore effort blended the emotional resonance of a relationship comedy with the immaturity of a group of wise-cracking friends in a film that balanced juvenile idiocy with adult levels of schmaltz (in a good way).

9. 'The Hangover' (2009)

The Hangover
Warner Bros.

There's a reason why Todd Phillips' Las Vegas road trip movie became the highest grossing R-rated comedy in history. Recounting one long – okay, very long – night in Vegas between a fiancé and his three friends, the film starts with a missing tooth, impaled mattress, anonymous baby, wandering chicken, police cruiser and hospital bracelet. And that’s one of the normal scenes. We've seen Las Vegas in movies countless times, but never has a film conjured up such fantastical scenarios.

8. 'Best in Show' (2000)

Best in Show
Warner Bros.

No one has mastered awkward, improvisational comedy more than "This is Spinal Tap" and "Waiting For Guffman" director Christopher Guest. With the Mayflower Kennel Club Dog Show as the milieu, Guest skewers neurotic, overprotective dog lovers ranging from the ultra-preppy to hickish. With Guest's movies, character trumps all and the cast, including Guest vets Eugene Levy, Fred Willard and Catherine O'Hara, clearly put their vast improv skills to use. It’s not your typical big-budget comedy, but still makes us laugh every time we see it.

7. 'Zoolander' (2001)

Zoolander
Paramount

On paper, the idea of Ben Stiller and Owen Wilson as competing male models sounds like a straight-to-DVD release. In practice, the film is not only a incendiary satire on our culture's obsession with beauty and the superficial, but an absurdist masterpiece, filled with random one-liners that are simultaneously brilliant and idiotic. No opportunity for humor is missed. Why is Mark Ronson DJing a funeral? Why does Hansel roll to an awards show on a child's scooter? Why the gasoline fight interlude? Don't think. Just laugh.

6. 'Shaun of the Dead' (2004)

Shaun of the Dead
Focus

The phrase "romantic zombie comedy" could admittedly be tantamount to "disaster," but director Edgar Wright, along with longtime collaborators Simon Pegg and Nick Frost, deftly found the sweet spot between horror and humor. Wright flips the age-old zombie movie into a tale of a 29-year-old directionless salesman named Shaun whose girlfriend dumps him and whose every night is spent drinking at a nearby pub. When the zombies attack, Shaun is revitalized, finding a new sense of purpose amid the oncoming apocalypse. Zombie attacks have never been funnier.

5. 'Tropic Thunder' (2008)

Tropic Thunder
Paramount

Following on "Zoolander's" absurdity, Ben Stiller's jungle adventure spoofs scumbag agents and deceitful producers, war movies like "Apocalypse Now" and "Platoon" and method actors that take their roles a little too seriously. For the latter, Robert Downey Jr.'s transformation into a black actor sparked a little controversy, but most accepted the performance as a parody of the lengths actor will go to nail the role. And he's definitely right about one thing: You never go full retard.

4. 'Anchorman: The Legend of Ron Burgundy' (2004)

Anchorman
DreamWorks

Arguably the pinnacle of Will Ferrell's career so far, Anchorman plays up the two qualities Ferrell does best: clueless and arrogant. Ferrell and director Adam McKay put together a perfect supporting cast in Paul Rudd, David Koechner, Steve Carell and Christina Applegate, but it's to Ferrell's credit that narcissistic misogyny can be played to such laughs. As Ron Burgundy, the scotch-drinking, jazz flute-playing protagonist, Ferrell may have the best deadpan delivery in comedy. And like the best absurdist comedies on this list, it's random scenes like the giant newscaster riot that make no sense and perfect sense at the same time.

3. 'Borat' (2006)

Borat
Fox

British comedian Sacha Baron Cohen was already well known in his home country for his portrayal of multiple characters, most notably the white, hip-hop loving Ali G and gay Austrian fashion reporter Bruno. But when Borat, the Kazakhstan journalist, traveled to the United States to interview Americans in this largely improvised film, a phenomenon was born. Set aside the catchphrases and recognize Cohen as one of the world's foremost satirists, as the comedian repeatedly exposes the prejudices and ignorance of people through his own feigned naïveté. It’s the perfect mix of high and low art.

2. 'Old School' (2003)

Old School
DreamWorks

In 1998, director Todd Phillips went undercover to expose the darker side of fraternities in "Frat House." Five years later, he revisited the subject from a different angle, corralling perpetual man-boys Luke Wilson, Will Ferrell and Vince Vaughn as thirtysomething guys who became Big Men on Campus at fictional Harrison University. Phillips excels at the debaucherous and lecherous, and the central conceit of grown men starting a fraternity allows the cast, and viewer, to indulge in the types of activities you either remember doing or wish you did.

1. 'The 40-Year Old Virgin' (2005)

The 40-Year-Old Virgin
Universal

You knew it'd be either Apatow or McKay that takes the crown, right? Apatow's debut about Andy Stitzer, a middle-aged virgin on a quest to finally get laid, remains his best film. Steve Carell, as our titular hero, goes against type, never going over the top and playing Andy as the friendly, geeky guy you'd see alone at the movie theater on the weekend. The cheap laughs are plentiful – "You know how I know you're gay?" became a catchphrase for years and good luck seeing the chest-waxing scene without wincing – but underneath, the film empathizes when it could easily mock. This mix of crude humor and quaint sentimentality would become Apatow's trademark, but never was it better than here.

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