Top 10 Funniest Movies – The 00’s

Article by Zach Saltz

Posted - 10/21/09

Go to Top 10 Funniest Films List

The 2000s in comedy showed tremendous promise with the unexpected rise of a new great comedic talent in motion pictures by the name of Jack Black.  Equipped with two of the decade’s funniest film roles (Dewey Finn and Barry from Top 5 Records), Black showed all the untapped potential of a burly physical comedian in the tradition of Bud Abbott and John Belushi.  Unfortunately, by decade’s end, he had been reduced to starring in films opposite Michael Cera where he had to wear a toga, and other films where spandex was involved.  Perhaps he owns a few spots on the “gross-out films of the 2000s” list as well.

I have accompanied my selections with some of their funniest lines.  Yes, I suppose I’m spoiling the best parts of these movies, but it will entice you to see them, will it not?  My runners-up would be: Ghost World (2001), Mean Girls (2004), Starsky and Hutch (2004), and Fever Pitch (2005). 

10. 50 First Dates (Peter Segal, 2004).  It’s no masterpiece, but it is one of Adam Sandler’s best films, which really isn’t saying too much except to say that it is sweet and rather genuine when it doesn’t show Rob Schneider getting a bunch of walrus shit getting poured on top of him (OK OK, I snickered a little at that).  The premise is rather sweet and Groundhog Day-like, and has a nice kind of rhythm that keeps the story engaging and fun, even when the material begins to wane.  Sandler is somehow a little more real here than he was in Happy Gilmore et. al. and the mood is funny and light, rather than depraved and masochistic.

Henry Roth (Adam Sandler): Yeah? Why don't you choke on your spam!

9. Bruno (Larry Charles, 2009).  Sasha Baron Cohen is indeed an artist, and demands a tremendous amount of respect for the art that he seamlessly crafts.  In the case of the savagely transgressive Bruno, the art is relentlessly lampooning stupid celebrities and unsuspecting political and militant leaders that have had it coming all along.  The results are far superior to Borat, and the jokes are only half the fun – the real pleasure is seeing how far Cohen will go just for a single laugh.  He is compulsively obsessed with entertaining his audience, a very commendable trait in the enfant terrible of modern comedy that he has become.

Bruno (Sasha Baron Cohen): Can I give you guys a word of advice? Lose the beards, because your King Osama looks like a kind of dirty wizard . . . or a homeless Santa.

8. The 40 Year Old Virgin (Judd Apatow, 2005).  Apatow became a household name in comedy by the end of the decade, but this is really his only great comedic contribution to modern film, and this is more the result of Steve Carell’s charisma rather than the dialogue (occasionally hit-or-miss) and the overlength (a staple of all Apatow films).  Nevertheless, the raunchy and ribald nature of this movie make it somehow all the more appealing and charming, in a strange way, and as we’ve seen on other films of this list, the “buddy” dialogue between the main male characters (between three of the great comedic talents of the decade – Carell, Seth Rogan, and Paul Rudd) is positively pristine.

Andy Stitzer (Steve Carell): I hope you have a big trunk . . . because I'm puttin' my bike in it.

7. Grindhouse (Robert Rodriguez and Quentin Tarantino, 2007).  A film that doesn’t quite fit with the others on this list for two reasons: One, because a large portion of it (Tarantino’s film) is neither funny nor engaging, and two, neither feature is played directly as a comedy.  Instead, the comedy (at least from Rodriguez’s film) is from the “intentional unintentional” camp of 70s Z-grade zombie flicks and the positively uproarious collection of faux trailers that lie at the intermission between the films.  Watching ten minutes of these trailers makes the other two hours and fifty minutes of this behemoth shrine to geekdom quite worth it for skeptical fans indeed.

Trailer Voice-Over: And . . . Nicholas Cage as . . . Fu Manchu!

6. Adaptation. (Spike Jonze, 2002).  It’s hard to decide what’s funnier: Nicolas Cage’s magnificent performance as Charlie Kaufman’s twin brother/cinematic doppelganger Donald, describing the conflict in society between modernity and the horse, or Chris Cooper’s Oscar-winning performance as trashy John LaRoche, illegally hoarding rare orchids by luring Native Americans to perilously trek across the waters of the Everglades as Meryl Streep observes him.  Perhaps the most hilarious element is Charlie Kaufman’s whimsical, offbeat mind, full of odd characters and self-defeating pessimism about the human condition – the kind of pessimism that always makes for the funniest kind of comedy.

Charlie Kaufman (Nicolas Cage): Here you go. The killer's a literature professor. He cuts off little chunks from his victims' bodies until they die. He calls himself "the deconstructionist.

5. Meet the Parents (Jay Roach, 2000).  A bruised-forearm comedy – that is, a comedy that is painful to watch because of the laughably absurd situations the protagonist, one Greg Focker (Ben Stiller), seems to consistently find himself in.  The film also serves as a reminder to Robert De Niro’s terrific comedic talent, as he plays off the image he was so meticulously developed over the last several decades of cinema.  The exchanges between Stiller and De Niro are pure comic gold, and there is a fine comic turn by Owen Wilson.  Somehow, the “Focker” jokes never seem to get boring.

Greg Focker (Ben Stiller): Oh, you can milk just about anything with nipples.

Jack Byrnes (Robert De Niro): I have nipples, Greg, could you milk me?

4. High Fidelity (Stephen Frears, 2000).  John Cusack is charming, Todd Louiso does his best Todd Plucknett imitation, but the film ultimately belongs to Jack Black, as he turns away customers at Cusack’s record store by telling them not to buy certain albums because they are “sentimental tacky crap.”   The “buddy comedy” exchanges between the three central characters is savagely witty and has echoes of Diner, a film whose male characters also knew less about women than they did pop culture and taste.  But in the firm directorial hands of Frears, the screenplay is surprisingly sophisticated and rather disarming, and the infusion of debates over pop music is always entertaining.

Barry (Jack Black): We're no longer called Sonic Death Monkey. We're on the verge of becoming Kathleen Turner Overdrive, but just for tonight, we are Barry Jive and his Uptown Five.

3. Sideways (Alexander Payne, 2004).  Probably the best overall film on this list, Sideways fits well within the Woody Allen-Albert Brooks oeuvre of a self-deprecating cynic at the center of the story (a tremendous performance by Paul Giamatti) accompanied by an offbeat and hilarious sidekick (Thomas Hayden Church).  The screenplay is deft, dry, and literate, with keen observations on friendships, loyalty, relationships, and of course, wine.  But the banter between Giamatti and Church is the best thing about the film, and heightens the mood of what otherwise could easily be qualified as a “downer” film.

Miles Raymond (Paul Giamatti): No, if anyone orders Merlot, I'm leaving. I am NOT drinking any fucking Merlot!

2. The School of Rock (Richard Linklater, 2003).  On paper it doesn’t sound particularly special: Jack Black teaching a bunch of rowdy schoolchildren how to play guitars and rock out.  But the film works because of Black’s manic energy, his insatiable likeability, and the terrific unforced exchanges he has with the children in the film, all surprisingly good actors in their own right.  The film could have gone wrong in so many ways, but somehow it never does: Case and point, the stern principal of the school, played by Joan Cusack, is not the stuck-up bitch in the Dean Wormer tradition we’re accustomed to seeing, but a funny and intriguing character who enhances the comedic tension and resolve.  It’s hilarious from start to finish, and completely exonerates Black from any of the recent comedic flops he has made.

Dewey Finn (Jack Black): You don't have to worry about me because I'm a hard-ass. And if a kid gets out of line, I got no problem smacking them in the head.

1. Best in Show (Christopher Guest, 2000).  Christopher Guest and Michael McKean, the bad boys behind the funniest movie of the 1980s (This is Spinal Tap) and one of the 1990’s funniest (Waiting for Guffman), again struck gold with this rich, intensely engaging, off-the-wall comedy that is bawdy, raucous, subversive, and consistently hilarious.  A harbinger of the “faux-documentary” approach that dominated television and film comedy by the end of the decade, the spotlight performances here (and there are many) include Eugene Levy and Catherine O’Hara as the hapless Flecks, whose canine ultimately takes top prize, John Michael Harris as the flamboyantly gay owner of an ornately decorated Shih Tzu, and Guest himself as the auspiciously named Harlan Pepper.  Fred Willard has some of the best lines of any comedy, and the visual gags and double entendres are ceaseless and fantastic.

Harlan Pepper (Christopher Guest): Macadamia nut. Pine nut, which is a nut, but it's also the name of a town.  Pistachio nut.  Red pistachio nut.  Natural, all natural white pistachio nut.