Anchorman: The Legend of Ron Burgundy
(2004, Adam McKay)
Will Ferrell's finest hour. A hilarious examination of hubris, chauvanism and disastrous '70s fashion, the corps of actors (including David Koechner, Steve Carrell, Paul Rudd and Christina Applegate--not to mention cameos from Luke Wilson, Tim Robbins and Ben Stiller) were all in peak improvisational form, making this one of the most quotable movies of the decade.
Best Line: "I killed a guy with a trident!" - Brick (Steve Carell)
Best in Show
(2000, Christopher Guest)
The always reliable crew of Christopher Guest (whose number is too large to count) doesn't really act so much as brilliantly ad-lib their way from scene to scene. This tale of beyond-obsessed dog owners on their way to a competition is filled with awkwardness (thanks to Eugene Levy), an abundance of nut knowledge (thanks to Christopher Guest) and dogs dressed as Clark Gable and Vivien Leigh (thanks to John Michael Higgins and Michael McKean).
Best Line: "We met at Starbucks. Not at the same Starbucks but we saw each other at different Starbucks across the street from each other." - Meg Swan (Parker Posey)
Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan
(2006, Larry Charles)
A movie that has the brains to go with the laughs. Going undercover as bumbling, racist reporter Borat Sagdiyev, Sacha Baron Cohen revealed the worst parts of human nature with a big, dopey grin and uncontrollable laughter. The scenes are funny not because they are uncomfortable, but uncomfortable because they are funny. Brüno tried to replicate this formula, but with less success.
Best Line: "May George Bush a-drink the blood of every single man, woman, and child of Iraq!" - Borat (Sacha Baron Cohen)
(2009, Todd Phillips)
Here's a movie that by all accounts shouldn't have broken any new ground or been any better than your latter-day National Lampoon venture. But it was. And not because it was raunchy, but because it was genuinely funny and intriguing. Hats off to a potential Best Picture nominee.
Best Line: "What do tigers dream of/When they take a little tiger snooze?/Do they dream of mauling zebras/Or Halle Berry in her Catwoman suit?/Well, don't you worry your pretty striped head/We're gonna get you back to Tyson and your cozy tiger bed/And then we're gonna find our best friend Doug/And then we're gonna give him a best friend hug/Oh, Doug!/Oh, Doug!/Dougie, Dougie, Doug-Doug/But if he's been murdered by crystal meth tweakers/Well, then we're sh*t outta luck." - Stu (Ed Helms)
(2007, Edgar Wright)
The Brits strike back! After delivering an impressive debut with Shaun of the Dead, Edgar Wright brought back Simon Pegg and Nick Frost for this loving tribute to cop movies both good (Point Break) and bad (Bad Boys II). Is it hilarious even if you're not into British humor? Yarp!
Nicholas Angel (Simon Pegg): "He's appointed himself judge, jury and executioner!"
Danny Butterman (Nick Frost): "He's not Judge Judy and executioner!"
(2003, Tommy Wiseau)
A complete travesty on every single level, this is not only the worst movie ever made, but also the worst-made movie ever. Still, that doesn't stop it from being wildly entertaining, with its atrocious dialogue, subplots that go nowhere and horrific sex scenes that go on way too long. In other words, it's a masterpiece.
Best Line: "You are lying! I never hit you! You are tearing me apart, Lisa!" - Johnny (Tommy Wiseau)
State and Main
(2000, David Mamet)
Mamet's style certainly isn't for everyone, but this out-of-the-blue comedy (if you know anything about Mamet, you know he's best at twisty, F-word-laden dramas) about a film production that may never finish is relentlessly funny. Each character has a personality (gasp!) and a bevy of funny lines. Plus, there's a touch of something you never find in a Mamet movie: sweetness.
Best Line: "Who designed these costumes? It looks like Edith Head puked, and that puke designed these costumes." - Walt Price (William H. Macy)
(2007, Greg Mottola)
Despite containing some of the most vulgar dialogue since Clerks, this film has a heart beneath its rough exterior. All the frustration of teenage life (especially if you're not in the upper echelon of popularity) is on full display here, but with a shield of humor. And even if the wacky cop subplot belongs in a different movie, it's still gut-busting.
Best Line: "I'm sorry the Coen Brothers don't direct porn." - Seth (Jonah Hill)
Team America: World Police
(2004, Trey Parker & Matt Stone)
More entertaining than most Michael Bay movies, funnier than most Eddie Murphy movies, this marionette-starring action comedy blows doors and delivers laughs by the ton. Part of a tremendous balancing act between stupid and smart comedy, the creators of South Park pull it off unbelievably well. Remember: the real enemy are celebrities who think we want to hear their political opinions.
Best Line: "When you see Arec Barrwin, you see the true ugriness of human nature." - Kim Jong-Il (Trey Parker)
(2001, Ben Stiller)
Who's one of the funniest characters ever created? One name and five syllables: Der. Ek. Zoo. Lan. Der. Though it could have failed miserably (ask SNL how many of its sketches have turned into funny movies--the answer is two and a sequel), this Manchurian Candidate (and apparently Glamorama) rip-off provides the laughs, even if the inept character only has one look.
Best Line: "You're dead to me, son. You're even more dead to me than your dead mother." - Larry Zoolander (Jon Voight)