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The Ten Best Movies of the 2000s: Comedy

Black Comedies

The end of the ’00s can mean only one thing: everyone and his mother writing and sharing their Ten Best Movies lists. As you can see, I’m no better than they are. But just for kicks and giggles, I’ve divided mine in half – ten dramas, ten comedies. My picks for the ten best dramatic films of the last ten years can be found right here. As for my list of the decade’s ten best comedies . . . well, just hang on. Here it comes:

High Fidelity (U.S. release: March 31, 2000) – Many things make this adaptation of Nick Hornby’s novel a great comedy. It’s hilarious, it has great performances by John Cusack (who also co-wrote the screenplay), Jack Black, and Tim Robbins, but here’s the most important factor: it’s just so damn likable. Even when he admits to cheating on his girlfriend just prior to her having an abortion, even when we watch him consider cheating on the same girl again shortly after a reconciliation, it’s impossible to hate Cusack, who stars as Chicago record store owner Rob Gordon, who deals with his latest break-up by revisiting girlfriends of the past, breaking the fourth wall to narrate all the way. It’s among the best comedies of the decade, and one of the best on this list, because it is funny, but not just funny.

American Psycho (U.S. release: April 14, 2000) – Think this one’s on the wrong list? You’re probably not alone. Even nine years later, a lot of people misunderstand Mary Harron’s gleefully bloody adaptation of the novel by Bret Easton Ellis. Upon its release it was controversial, mostly among prudes and people who mistakenly took it to be in earnest. But this one is comedy through and through, from the absurdly serious business card swap, to Patrick Bateman’s deep appreciation of the music of Huey Lewis and Phil Collins, to the running gag of no one being able to remember Bateman’s name even when he’s confessing to a string of brutal murders. It’s a vicious satire, mocking a group of people – ’80s yuppies – who still have it coming in spades. If you’re not laughing at Christian Bale’s star-making performance as Bateman, you’re missing the point.

Adaptation (U.S. release: December 6, 2002) – This one, which revolves around a fictionalized version of screenwriter Charlie Kaufman and his totally fictional twin brother Donald (both played by Nicholas Cage), could easily have been self-conscious inside baseball. Instead, Kaufman (the writer, not the character) and director Spike Jonze make Adaptation into a biting show business satire, and a heartfelt character study. Joining Cage are the always outstanding Chris Cooper as a toothless yet compelling orchid poacher, and Meryl Streep as the journalist who authored the book Kaufman (the character) is struggling to adapt. There’s also Brian Cox, who gets some of the funniest scenes in the movie as screenwriting guru Robert McKee, including perhaps the best line in a movie filled with great dialogue: “I need more.”

Punch-Drunk Love (U.S. release: November 1, 2002) – Adam Sandler has made a pretty good career for himself playing outlandish characters in interchangeable comedies, but the 2000s was the decade when he also decided to try his hand at serious acting. Before his more heavily hyped turns in Spanglish, Reign Over Me, and Funny People, Sandler starred as Barry Egan, a plunger salesman with serious anger issues, in this odd and wonderful film by Paul Thomas Anderson. There are laugh-out-loud moments, like when Barry threatens to kill his sister is she refuses to give him a girl’s phone number, or when he compliments love interest Emily Watson by sweetly whispering his desire to smash her face, or pretty much every second Philip Seymour Hoffman is onscreen, but Punch-Drunk is more designed to elicit knowing smiles than raucous laughter. Despite its title, the movie cares less about punchlines and more about heart, sweetness, and sincerity.

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Lost in Translation (U.S. release: October 3, 2003) – Sofia Coppola’s second feature as a writer and director was the best film of 2003 – get bent, Return of the King. Like many of the titles on both this and my drama list, Lost in Translation defies categorization. It’s a love story, but not of the ordinary “boy meets girl, boy gets girl” type. It’s a “fish out of water” story, but uses that situation to examine themes of loneliness and alienation in a much deeper way than just to provide setups for jokes. One thing it is, definitively, is a comedy. Bill Murray’s justly praised performance is sad and wistful, sure, but it’s also incredibly funny. See the filming of the whisky commercial, or Scarlett Johansson’s deadpan reaction to Anna Faris’s uncanny Cameron Diaz impersonation if you need reminding. 2003 was the year of the self-serious, overblown epic, but Lost in Translation emerged as the year’s best film by focusing on characters and human relationships, and the laughs and truths to be found therein.

Bad Santa (U.S. release: November 26, 2003) – Of the ten films on this list, seven are here because they are funny plus something else. Not just great comedies, they’re great movies in a broader sense. The other three, the first of which is Terry Zwigoff’s Bad Santa, are here for how incredibly hard they made me laugh. It looked for awhile like there wouldn’t be a funnier movie this decade than Bad Santa, the story of an alcoholic mall Santa and his dwarf/elf partner, who make a living robbing their employers on Christmas Eve before moving on to another location the following year. Like American Psycho, it stirred controversy at the time of its release. Apparently some people don’t think black comedies about men who dress up as fictional holiday icons ought to be allowed. I am not one of those. I am one who thinks Billy Bob Thornton’s performance as whisky-soaked Willie is the best of his career, and that Bad Santa is one of the funniest movies ever made.

Sideways (U.S. release: October 22, 2004) – Character-driven comedies can be difficult to pull off. It’s easier to go for the cheap laugh, more difficult to mine humor from things like human behavior and everyday situations. Not that all the situations in Alexander Payne’s Sideways qualify as “everyday” – when was the last time you had to steal back your best friend’s wallet from a stranger’s house, and were chased out by the enraged – and enormous – and naked – husband of the woman your buddy had slept with the night before? Still, most of the laughs come from the interactions of Miles (Paul Giamatti) and Jack (Thomas Haden Church) with each other, and with the women (Virginia Madsen and Sandra Oh) who become the objects of their affection during a trip through California’s wine country prior to Jack’s imminent wedding. Giamatti did what he does better than just about anyone: play a lonely neurotic. Church and Madsen were good enough in their roles to earn Oscar nominations, and Alexander Payne picked up a nomination for Best Director, and, alongside his co-writer Jim Taylor, a well-deserved win for Best Adapted Screenplay.

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Little Miss Sunshine (U.S. release: July 26, 2006) – How, oh how do I love this damn movie . . . One of my very favorite films – comedy or drama, of this or any decade – Little Miss Sunshine tells the story of little Olive Hoover, an aspiring beauty queen who is thrilled to learn she will compete in the Little Miss Sunshine pageant in Redondo Beach, California, and the members of her profoundly dysfunctional family who uproot their lives to get her there from the family home in Albuquerque in time. Olive is played by Abigail Breslin, who is supported by a uniformly outstanding cast – Greg Kinnear as her father, the failed motivational speaker; Toni Collette as her frazzled, put-upon mother; Steve Carell as her uncle, a suicidal Proust scholar; Paul Dano, her half-brother, who has taken a vow of silence while preparing to enter the United States Air Force; and Oscar-winner Alan Arkin as her doting, heroin-snorting grandfather. Writer Michael Arndt and directors Jonathan Dayton and Valerie Faris introduce us to the characters in an opening montage of superficial images (Olive watching an old Miss America tape, Dwayne lifting weights, Grandpa . . . snorting heroin, etc.), then spend the rest of the film letting us see the characters transcending their simplistic introductions. The result is a movie that is funny – sometimes blackly funny – and genuinely moving, like a warm hug from a good friend.

Borat (U.S. release: November 3, 2006) – Here is one of the funniest films of the decade, and one of the most inescapable. Borat the movie, and Borat the character, Sascha Baron Cohen’s anti-Semitic Kazakh TV host, were everywhere in late 2006, with Cohen appearing in-character at premieres and on talk shows to promote the film. It worked – Borat eventually grossed over $250,000,000. More to the point, it deserved every penny. Yes, it will probably last longer as a meme than as a movie, and yes, we have this film to blame for the unfortunate phenomenon of people assuming a bad Borat impression is somehow funny in and of itself, but those side effects don’t change the fact that the movie itself is breathlessly, painfully, fearlessly funny. Borat, like Beavis and Butt-Head before him, is designed to be laughed at, not with, and Cohen uses him to skewer a dizzying array of targets, from drunken white college students, to sober black politicians, to homophobic rodeo cowboys. And come on, how do you not love a movie that was banned in the entire Arab-speaking world except for Lebanon?

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Tropic Thunder (U.S. release: August 13, 2008) – At last we arrive at the funniest movie of the decade. It also just so happens to be the most recent, and thus the last one on the list. I swear I didn’t plan it that way. Tropic Thunder, co-written and directed by its star, Ben Stiller, is so incredibly funny partially because it shouldn’t be. It treads such familiar territory – action comedy, showbiz comedy, film-within-a-film – yet finds fresh and exciting ways of exploring that territory. Stiller stars as action icon in decline Tugg Speedman, who signs on to star in a Vietnam War picture based on the memoirs of “Four Leaf” Tayback, who was the sole survivor of a Viet Cong ambush that cost him his hands and his comrades their lives – or so Tayback says. Joining Speedman in the cast are Kirk Lazarus (Oscar nominee Robert Downey Jr.), a method actor who underwent a skin-pigmentation procedure to play his African American character; Jeff Portnoy (Jack Black), an overweight heroin-addicted comedian who stars in broad comedies like The Fatties, a take-off on Eddie Murphy’s Nutty Professor; rapper Alpa Chino (Brandon T. Jackson), who is in the movie in the hopes that the role will boost sales of his Booty Sweat energy drink; and Kevin Sandusky (Jay Baruchel), an up-and-coming young actor who is the only member of the cast to have actually read the script. There’s also Steve Coogan as the film-within-a-film’s desperate director, Nick Nolte, crazier than ever as “Four Leaf” Tayback, and Tom Cruise in a hysterical, revelatory performance as Les Grossman, the mercenary producer who, in one of the movie’s funniest scenes, attempts to persuade Speedman’s agent to allow the cast to die at the hands of Southeast Asian heroin traffickers in order to collect the insurance. Tropic Thunder is smartly written, everyone in the cast looks like they’re having a great time – particularly Downey, who is so good as Lazarus that you could make a case that he deserved that Best Supporting Actor Oscar more than Heath Ledger – and it’s hilarious from start to finish, making it the funniest film of the decade, and one of the best.