Top 10 Funniest Movies – The 00’s

Article by Todd Plucknett

Posted - 10/21/09

Go to Top 10 Funniest Films List

This decade has been an interesting bunch of years for comedy. As shown by my list, it was the back half of the decade that produced the best and funniest comedies. This is no doubt due to Judd Apatow bursting onto the scene creating arguably the 2 best comedies of the past 15 years. He changed the genre. Another trend in the industry that I saw was a tendency to make movies about making movies. Four of my favorite comedies of the decade are with this focus (For Your Consideration, Tropic Thunder, State and Main, and What Just Happened). For whatever reason, those are comedies that really appeal to me and why they have respectable showings on my list.

I am not the biggest fan of this genre. Don’t get me wrong; when it works, it is hard for anything to touch it. When it is not funny, however, there is no bigger waste of time. Sadly, most of them are in this vein. This list is of the 10 films this decade that definitely did work and struck my funny bone the most over the past 10 years:

Honorable Mention: Walk Hard: The Dewey Cox Story (2007), For Your Consideration (2006), The School of Rock (2003), Anchorman: The Legend of Ron Burgundy (2004), Harold & Kumar Go to White Castle (2004)

10. The Aristocrats (2005). This is almost certainly going to be the only documentary on any of our lists. It is almost not a documentary, though. It is like a sketch that is stretched (but never too thinly) over 89 minutes of pure hilarity. It is about 100-some comedians and the dirtiest joke ever conceived called “The Aristocrats”, which is an inside joke privately held and passed on to each standup comedian in the industry. Every comedian interviewed has their own version of the joke, and they all try to one-up each of their peers by making their version even dirtier, even raunchier, and in most cases, even more hilarious. It is a pleasure to watch all of our favorite comedians just completely having a blast making a movie. The interviews include everyone from Paul Reiser, Sarah Silverman, Chris Rock, George Carlin, and everyone in between. It is just too awesome to ignore on this list.

Robin Williams: You'd never hear a physicist going, "It's a muon, you cunt."

9. Shaun of the Dead (2004). There has been a trend in the industry to make spoofs of other film genres. Arguably the best ones spoof of the zombie genre, which is best represented in the 2004 film Shaun of the Dead. It is one of the wildest experiences you will have at the movies, and one of the most comical. Simon Pegg is one of the most awkward comedians out there, and this is his best work. Shaun and Ed are two incredibly likable characters, and the audience will no doubt enjoy hanging out with them for a hilarious hour and a half. This genre was also done justice with the recent Zombieland. It’s just refreshing to know that not every film spoof is done by those morons who did Date Movie and what not.

Shaun (Simon Pegg): As Mr. Sloan always says, there is no I in team, but there is an I in pie, and there's an I in meat pie. Anagram of meat is team... I don't know what he's talking about.

8. Tropic Thunder (2008). The funniest film of 2008, a rather good year for comedy, was undoubtedly Tropic Thunder, a film about an oddball group of actors trying to create a huge-budget Vietnam War film. There is the action star, the Oscar-winner, the comedian, and a few others. It creates perhaps the finest comedy ensemble cast this side of a Wes Anderson movie, with unforgettable characters played by Ben Stiller (Tugg Speedman / Simple Jack), Robert Downey Jr. (“the dude playin’ the dude disguised as another dude”), and of course Tom Cruise in one of the smallest and easily most hilarious role of career. The movie just has so many laughs, especially if you are a true fan of film. There are some references that can only be caught by the eye of a hardcore movie aficionado. It is a wild, out-of-control comedy that will be considered a classic in years to come.

Kirk Lazarus (Robert Downey Jr.): You never go full retard. Ask Sean Penn, I Am Sam, 2001. Went full retard, went home empty-handed.

7. The Girl Next Door (2004). In the 1980s, there was Risky Business. In the 00s, there was The Girl Next Door, one of the funniest films of the decade that has an unexpectedly big heart. It is one of those films that may not seem like much on first viewing, but after a bunch more, the laughs pile up, and the characters wind up feeling like your friends. I have seen this about 10-15 times, and it has never lost a single ounce of appeal. It introduced us to future stars Emile Hirsch and Paul Dano, whose awkward idiosyncrasies make for much of the hilarity of the film. It is a sex comedy, yes, but, unlike several previous entries in the genre, it is one that will not get old and does not get its laughs from gross-out scenes alone.

Kelly (Timothy Olyphant): Hey, you guys know Matty? I hung with him last night. Guy's the tits!

6. Clerks II (2006). Kevin Smith is one of my favorite comedy writers, and Dante and Randall are two of my all time favorite characters. This film takes them out of the Quick Stop and into Mooby’s, a fast food restaurant. The cameos are as funny as anything else in this film, of course Jay and Silent Bob make Mooby’s their new home, and a crazy gag of inter-species erotica known as Kinky Kelly and the Sexy Stud provides a definite highlight. Smith’s token dialogue criticizing and analyzing everything in pop culture is the staple of the film, and it makes for one of his funniest and most interesting achievements as a director. Every bit of this film is just inspired comedy, and Smith’s films always have a shocking bit of depth in the end. This is no different. Revisiting these characters was one of my favorite comedy experiences this decade, and I cannot help but hope he revisits them again at some point in the future.

Randall (Jeff Anderson): All right, look, there's only one "Return," and it ain't "of the King" it's "of the Jedi."

5. The 40 Year Old Virgin (2005). What is there to say that hasn’t been said about Apatow? This was his first feature, and it changed the comedy genre. Every bit of this longer-than-usual comedy is inspired, sharp, hilarious, and brilliant. The ensemble is really what makes the film click, other than the flawless screenplay. Seth Rogan, Romany Malco, Paul Rudd, Steve Carell, and of course Catherine Keener create the most lovable group of characters in any comedy this decade. Spending two hours with these characters is likely going to be one of the best times you will have and will provide some of the most laughs of any comedy around. It is just a brilliant, uproarious comedy.

David (Paul Rudd): You know, I always thought that Matt Damon was sort of a Streisand, but I think he's rocking the shit in this one.

4. Superbad (2007). In the tradition of high school hangout films like Rebel Without a Cause, American Graffiti, and Dazed and Confused, Seth Rogan’s first writing effort Superbad burst onto the scene in 2007, setting the stage to become this generation’s version of the aforementioned films. Seth and Evan are two characters that anyone can relate to. Their awkward quirks, the way they talk, and what they talk to each other about take this film out of the heap of garbage comedies and place it as one of the most original and appealing comedies of the decade. The things that Seth and Evan get themselves into that night create a truly hysterical atmosphere. Oh yeah, and Apatow was involved…so it has heart. You don’t have to feel guilty for laughing at it.

Seth (Jonah Hill): Ok, I'm sorry that the Coen Brothers don't direct the kind of porn that I watch, they're kinda hard to get a hold of.

3. Knocked Up (2007). This is perhaps the greatest sex comedy ever made. Apatow strikes again. With a similar cast to his last film, Knocked Up seemingly came out of nowhere and blew audiences and critics away with its precise characters and uproarious laughs in a totally unique, yet believable setting. Ben and his group of friends create some of the funniest moments in the film. Then there is Leslie Mann, Craig Robinson, and my favorite lady comedian Kristen Wiig, who steal every moment of screentime they have with the stars of the film. What can I say? This is one of the funniest movies I have ever seen, and it is one of the very best films of 2007.

Ben Stone (Seth Rogan): If any of us get laid tonight, it's because of Eric Bana in Munich.

2. Sideways (2004). How can I ignore my #3 of all time? It is a rare film that gets better with each viewing, even when the viewing number get in the 30-40 range. There are so many great laughs in this film. It requires multiple viewings so you can pick up on all of them. I know the movie almost by heart, yet I am still laughing hysterically almost throughout. It is a film that earns every laugh it gets. Its perfect screenplay consists of wide-ranging knowledge of all media and a vocabulary so big that it is funny in itself. Miles is one of the most awkward leads in film, and he is matched with Jack, one of the best characters ever. It is a lot like Dante and Randall, actually. Never thought of that before…

Miles (Paul Giamatti): Oh, I like all varietals. I just don't generally like the way they manipulate chardonnay in California. Too much oak and secondary malolactic fermentation.
Jack (Thomas Haden Church): Huh...

1. Grindhouse (2007). This really is the funniest thing I have ever seen. When I saw it in theaters back in 2007 (with a tiny crowd by the way), I was totally mind-blown. It is movie-going at its absolute finest. It is so awesome, everything from the opening trailer Machete, to the mid-feature attractions Thanksgiving, Werewolf Women of the SS, and Don’t, to the missing reels and over-the-top car chases and gore scenes. This Robert Rodriguez-Quentin Tarantino homage to old drive-in grindhouse flicks from the ‘70s is the most hilarious movie imaginable. Rodriguez’s portion, Planet Terror, is a zombie film of sorts, which features some of the most awesome gore scenes this side of Evil Dead. Hilarious. Tarantino’s portion, the equally uproarious Death Proof, is about a stuntman serial killer whose weapon is his car. It has Tarantino’s token stretches of genius dialogue, which forms the lead-up to the insane car chases. By themselves, the movies are great. Together, it is the most perfect, most satisfying movie-going experience I have ever had.

Stuntman Mike (Kurt Russell): You know how people say, "You're ok in my book" and "In my book that's no good"? Well, I actually have a book. And everybody I ever met goes in this book. And now I've met you, and you're going in the book too. Unfortunately, now I'm gonna have to file you under...chicken shit.