I had a bit of a conundrum when coming up for a title for the article. Perhaps Funniest Movies of the 00s would have been better. I guess history will tell us whether this decade will be considered the 2000s, or the 00s. Anyways, I digress. Here are my picks for the best comedy films of the decade:
50 – Hitch – Will Smith, Eva Mendes and Kevin James from The King of Queens star in this romantic comedy about a jaded love doctor who finds the true love he didn’t believe existed.
49 – The Matador – Pierce Brosnan of James Bond and Remington Steele fame shows he has a talent for quirky comedy in this dark comedy about assassination.
48 – Hot Fuzz – Simon Pegg and Nick Frost serve up the laughs in this hilarious British cop spoof.
47 – My Big Fat Greek Wedding – One of the hugest indie films of all time, this unique romantic comedy’s popularity grew by word of mouth and by the end of its miracle run in 2002 it had made more money than many Hollywood blockbusters.
46 – Bruce Almighty – Though he was arguably the biggest name in comedy in the 90s Jim Carrey’s star has dimmed considerably in the new millennium. Still, he can still deliver the laughs as he proved in this 2003 comedy about a guy who is granted Godlike power.
45 – Orange County – Colin Hanks shows he has some of his father’s comedic talent, and Jack Black is his usual hilarious self in this film about a young man determined to get into Stanford University by any means necessary.
44 – Ice Age – This prehistoric animated film stars the voice talents of Ray Romano (Everybody Loves Raymond), John Leguizamo, Denis Leary and Jack Black. Though perhaps not in the same class as the Shrek series or the Pixar stable of films Ice Age has been immensely popular over the past decade, spawning a pair of sequels.
43 – Shallow Hal – Wow, Jack Black is all over this list of the best comedies of the 00s. His character believes that beauty is only skin deep, until he is zapped with a spell that forces him to see inner beauty. Gwyneth Paltrow’s fat suit may have sparked some controversy, but if you enjoy the movie in the spirit it was intended you’ll be laughing throughout.
42 – Zack and Miri Make a Porno – Expect to see Seth Rogen’s name a few more times on this list. He makes a rare break with Judd Apatow in this Kevin Smith-directed movie co-starring Elizabeth Banks about a pair of friends who go to great lengths to get out of dire financial straits.
41 – Kiss Kiss Bang Bang – One of the most underrated films on this list, this 2005 film starring Robert Downey Jr. may be played up as a murder mystery, but don’t let the plot tag line fool you – this is a comedy through and through. If you haven’t heard of this film, do yourself a favor and rent the DVD.
40 – The Aristocrats – Not so much a movie as an ongoing joke that gets cruder and cruder the further into it you get. George Carlin, Hank Azaria, Jason Alexander, Drew Carey and many, many more comedians and actors try to outdo each other with the crudest telling of this legendary Vaudeville joke.
39 – Beerfest – This one would take a high spot on a list of the best beer movies ever made. Goofy with marginal acting this movie will still make you laugh. It has become a favorite at our annual Oktoberfest party.
38 – Night at the Museum – Clever and fun for the whole family, this film starring Ben Stiller actually has some pretty spectacular special effects for a comedy film. The plot goes well beyond implausible, but if you can suspend your disbelief (it is a movie after all) there is plenty to love about this film. British comedian Ricky Gervais is hilarious in a supporting role.
37 – Finding Nemo – Speaking of great family movies, the 800 lb gorilla of animated films, Pixar, sure knows how to make them. Albert Brooks and Ellen Degeneres voice a pair of fish who traverse the ocean in search of a missing clownfish. Just as touching as it is funny and with spectacular animation this film belongs in everyone’s DVD collection.
36 – Team America: World Police – It might be far from politically correct, and its stars might be puppets, but if you aren’t easily offended, and can take some crude humor then this offering from Southpark creators Trey Parker and Matt Stone will be right up your alley.
35 – Road Trip – Fresh off his success as Steve Stifler in the 1999 comedy hit American Pie Sean William Scott co-starred in this 2000 film as basically the same Stifler character, convincing his buddy to drive across the country to correct a huge mistake.
34 – The Royal Tenenbaums – Though this quirky film might not be everyone’s cup of tea if you get the humor it is quite likely one of your favorite comedy movies of all time. Chock full of stars like Gene Hackman, Bill Murray, Ben Stiller, Gwyneth Paltrow the film about a very dysfunctional family provides constant laughs.
33 – American Pie 2 – Though I still like the original better personally, most people seem to prefer this 2001 sequel. The gags are taken to the next level, and Stifler, who was a peripheral character in the first film, gets a whole lot more screen time. It might seem a little dated now, but at the time this series of films had audiences howling.
32 – Rat Race – A Cannonball Run for the 2000s! This movie wasn’t well-received by critics and seems to engender a love it or hate it attitude among those who watch it, but those who love it have almost given the movie cult status with their praise for the film.
31 – O Brother Where Art Thou? – Though the Coen brothers never actually create movies that can be defined as comedies, several of their films routinely show up on lists of funny movies. The Big Lebowski, Fargo and this 2000 film starring George Clooney and John Turturro are all funnier than many so-called comedies.
30 – Harold and Kumar Go to White Castle – If this was a list of the best stoner movies of all time this film would definitely be near the top. Kal Penn and John Cho star as two buddies who get an incurable case of the munchies after smoking up, and risk life and limb as they take a fantastic journey to satisfy their craving for some WhiteCastle sliders.
29 – Blades of Glory – Will Ferrell and Jon Heder of Napoleon Dynamite fame star as a pair of disgraced figure skaters who get back on the ice after they find a loophole that allows them to perform again – as an all male pair.
28 – Kung Fu Panda – As a big Jack Black fan I was thrilled to see him cast as the voice of the lead character Po in this clever and funny spoof on kung fu movies. He wasn’t the only star lending his voice, with Angelina Jolie, Dustin Hoffman, Jackie Chan, Seth Rogen and more all lending their skills to this underrated animated film.
27 – Tropic Thunder – Robert Downey Jr. is back in a big way, first wowing audiences as Tony Stark in Iron Man, and then earning an Oscar nomination for his work in a supporting role on this film. Ben Stiller et al were all funny as well, but it was definitely Downey Jr.’s performance that made Tropic Thunder one of the funniest films of 2008.
26 – Austin Powers in Goldmember – Though not as funny as Austin Powers: International Man of Mystery or its sequel The Spy Who Shagged Me there was still enough funny juice in the tank to get the 3rd installment in this spy spoof movie trilogy onto the list. Hopefully Mike Myers can recapture his mojo and start cranking out some more good comedies.
25 – Dodgeball – Vince Vaughn doesn’t seem to make a bad movie, and he even delivers in this sports comedy about a group of average Joe athletes who must beat the odds in order to save the gym they love. Pepper needs new shorts!
24 – Talladega Nights: The Ballad of Ricky Bobby – Will Ferrell has made a living on sports movie spoofs and this one is arguably his best. He and John C. Reilly star as best friends and race car drivers whose friendship is put to the test when Ferrell’s career falls off the rails.
23 – Bad Santa – Forget Sling Blade, Bad Santa is the crowning jewel of Billy Bob Thorton’s acting career. As far away from Edmund Gwenn in Miracle on 34th Street as you can get, Billy Bob’s Santa is a boozer, a womanizer and a thief. Not really a comedy in the purest sense of the word, but extremely funny nonetheless.
22 – Clerks II – Kevin Smith’s original Clerks, shot in black and white on a miniscule budget, is a cult classic in the comedy genre. Thus, when a sequel was announced many fans met the news with mixed emotions. Could a sequel, now in color, live up to the high standard set by the original? Well, not really. But the film was still good enough to be considered one of the funniest movies of the 2000s.
21 – Shrek 2 – Mike Myers doesn’t have to worry about turning out live action duds as long as the Shrek series is around. This has been an enormous cash cow for the folks at Dreamworks, and with a second installment they did an admirable job of living up to the legacy of the first groundbreaking film. Antonio Banderas is particularly good in the role of Puss In Boots.
20 – Juno – Another film that isn’t strictly a comedy but is funny enough that it deserves a high spot on the list. Ellen Page gives the performance of her young life and Michael Cera is equally good in a supporting role in this clever film about teenage pregnancy.
19 – Forgetting Sarah Marshall – Jason Segel, who always finds himself relegated to supporting roles in Judd Apatow films, finally gets his shot at a lead role (he did write the screenplay, after all). Segel proves he has the chops to be a lead man, delivering plenty of laughs throughout this wacky romantic comedy, juggling both Mila Kunis and Kirsten Bell (what guy wouldn’t want to have that problem?) throughout the film.
18 – Zoolander – Ben Stiller, much like his father Jerry, is well known for his goofy, over the top brand of humor. He is in his element as Derek Zoolander, a male fashion model on the down slope of his career who ends up brainwashed and sent to kill the Prime Minister of Malaysia. Even the most jaded movie watchers won’t be able to resist at least chuckling at the scene where he has the “Walk Off” against Owen Wilson’s character Hansel.
17 – Knocked Up – Expect to see Judd Apatow’s and Seth Rogen’s names with increasing frequency as I move up this list. Both have been among the biggest forces in comedy over the past decade ever since working together on the TV show Freaks and Geeks. This film about a slacker (Rogen) who knocks up a career driven woman (Katherine Heigl) during a drunken one night stand really launched Rogen into the spotlight as a leading man.
16 – In Bruges – Arguably the most unheralded movie on this list of comedy films, In Bruges is another movie that is impossible to shoehorn into a single genre. Starring Colin Farrell as a disillusioned hit man burning time in Bruges, Belgium the movie’s dark sense of humor might not appeal to everyone’s tastes. But whether it makes you laugh or not it is still a great film and very much worth the DVD rental cost.
15 – Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan – Whew! The title is almost as long as my summary will be. Before he outraged audiences with Bruno, Sacha Baron Cohen was shocking moviegoers with 2006’s Borat. Almost painful to watch at times, and probably offensive in some way to just about everyone on the planet Borat definitely serves up the laughs and is definitely one of the funniest films to come along in years.
14 – Shaun of the Dead – One of the best horror movies of the past decade is also one of the funniest. This comedy horror zombie movie spoof is given a full dose of dry British humor and the result is hilarious. Simon Pegg, always brilliant, again delivers in the lead role, serving up laughs despite the gore much like Bruce Campbell did as Ash in the Evil Dead trilogy.
13 – Pineapple Express – Don’t look now, here come Apatow and Rogen again. This time Rogen plays a process server with a drug habit who winds up the target of a drug lord and a rogue cop after witnessing a murder. As good as Rogen is it is James Franco that really steals the show as Rogen’s overly friendly drug dealer/friend Saul Silver.
12 – Super Troopers – This one might not be on the radar of mainstream comedy audiences, but if you haven’t seen this spoof cop movie then you are definitely missing out. If you like Reno 911 then you will absolutely love Super Troopers. Goofy humor at its finest.
11 – The Incredibles – Definitely the funniest Pixar movie to date, this superhero spoof film might be first and foremost an action film, but trust me when I say you won’t stop laughing for more than a few seconds throughout the film. Don’t dismiss it as a children’s film. There is plenty here for adult audiences to enjoy as well.
10 – Van Wilder – As we enter the top 10 funniest movies of the 2000s some might disagree with the high spot I’ve given this film. Undisputedly raunchy and with some questionable acting at times this movie will still have you in stitches from the opening scene right until the end credits roll. Ryan Reynolds shows his incredible comedic talent, and Kal Penn is hilarious in his supporting role as Taj Mahal Badalandabad.
9 – Wedding Crashers – Vince Vaughn and Owen Wilson team up as two buddies living the bachelor’s dream. They crash weddings every weekend, lying through their teeth to work their way into the beds of young single bridesmaids. The dream team falls apart when Wilson’s character accidentally falls in love. Christopher Walken nearly steals the whole movie with another of his classic monologues.
8 – Napoleon Dynamite – Beyond quirky and into downright weird, Napoleon Dynamite is a film that will confuse as many people as it entertains. If you have the good fortune to be in the first group then prepare to laugh often and loudly.
7 – Meet the Parents – Ben Stiller and Robert De Niro aren’t two names you’d expect to see together on the billing of a comedy film. However, as unlikely a duo as they make it was definitely a good call by the casting director. Stiller is hilarious as male nurse Gaylord Focker, and De Niro is even funnier as ex-CIA agent and father of the woman Focker wants to marry. The volleyball scene alone is worth the rental price for this film.
6 – Old School – Though Luke Wilson’s Mitch Martin is the main character in this frat school comedy it is Will Ferrell’s “Frank the Tank” that has become one of the most iconic film characters of the past decade. “We’re going streaking!” is still widely quoted, and that is just one of his numerous classic lines. Throw in Vince Vaughn and Entourage’s Jeremy Piven and you’ve got pure comedic gold.
5 – Anchorman: The Legend of Ron Burgundy – Will Ferrell goes back to back, this time starring in the lead role as Ron Burgundy, a 1970s TV anchor whose perfect life goes awry when Veronica Corningstone (Christina Applegate) joins him on the news desk. Endlessly quotable and fun, this was the funniest film of 2004.
4 – The 40 Year Old Virgin – Steve Carrell has been a staple for the past 5 years on NBC’s hit sitcom The Office, but it was this 2005 comedy that really put him on the map. The title of the movie tells you everything you need to know about the plot, and the comedy never lets up. This is one of those rare movies that you can watch over and over again and laugh every time.
3 – Shrek – As funny as the two sequels were, the original still remains the gold standard when it comes to funny animated films. Mike Myers, Eddie Murphy, Cameron Diaz and John Lithgow are all hilarious, and the writing is top notch. A fantastic movie that kids can enjoy even though the adult humor will go flying over their heads, Shrek is not only one of the best animated movies of all time, but one of the funniest as well.
2 – Superbad – Jonah Hill and Michael Cera star as a pair of high school seniors who wind up in numerous misadventures when they try to acquire alcohol for a couple of girls they want to get with. Seth Rogen and Bill Hader are equally hilarious as two cops who don’t exactly enforce the law in a traditional sense, and Christopher Mintz-Plasse makes a spectacular debut as the now iconic character McLovin’.
1 – The Hangover – This film was an easy choice for the number one spot on the list of the funniest movies of the 2000s. Bradley Cooper, Ed Helms and Zach Galifianakis are all hilarious as three groomsmen who manage to loose their buddy and groom to be when they go to Vegas for his bachelor party. If you haven’t seen the film yet, then run, don’t walk before it leaves theaters. Definitely an all-time comedy classic.