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The 25 Best Comedies Of The 21st Century So Far

The 25 Best Comedies Of The 21st Century So Far

In Preston Sturges’ comedy masterpiece “Sullivan’s Travels” (hey, read our Struges retrospective here!), Joel McCrea plays a young Hollywood director who, fed up of making nothing but low-rent comedies, sets out to make a serious, important picture, only to realize at a screening of a Disney cartoon, that more good comes from his simple, unpretentious laughers than from his more worthy work.

As it ever was, so it ever shall be. Today, comedies don’t get any more respect than they did 73 years ago when Sturges was making his movies: dismissed and sniffed at by critics, ignored by awards bodies and undervalued by moviegoers. Yet comedy is arguably the hardest kind of movie to make, and when they’re made well, you end up with a film that gives immeasurable pleasure to millions for years to come.

We’re a way into our series on the Best Movies Of The 21st Century So Far (catch up on horror, animations, music documentaries and sci-fi), and with a comedy-packed summer including “Spy,” “Trainwreck,” “Dope,” “Ted 2,” “Vacation” and more on the way, we decided the genre was the next logical step. We decided to keep the list to pure, unfiltered comedies —dramedies like “Almost Famous” or “The Descendants” will be saved for a separate piece down the line. Nevertheless, we’re sure there’ll be some omissions you can quibble over, so take a look below, and let us know your own favorites in the comments.

25. “Tropic Thunder” (2008)
On the long list of potentially offensive areas that most studio comedies would balk at even implying, blackface has to be pretty near the top. But it’s a territory that Ben Stiller’s “Tropic Thunder” does not just flirt with —it barrels right in, courtesy of Robert Downey Jr’s finest (Oscar-nominated) comedic hour as the five-time Academy Award-winning Aussie Method actor Kirk Lazarus. But the film has so much more to offer than simply RDJ pulling an Al Jolson. From the fake movie trailers to Tom Cruise as a fat balding studio honcho to the phrase ‘going full retard’, almost all of the film’s many jokes land, perhaps because what its satirizing is so worthy of send-up: the delusions of Hollywood actors that the experiences they have are somehow equivalent to the real-life tribulations undergone by their characters’ inspirations. In a time when political correctness has the deadening effect of grinding many films down to unobjectionable, bland paste, “Tropic Thunder” is a spicy, courageous treat, sideswiping several sacred cows with commitment, intelligence and fart gags.

24. “The Trip” (2010)
Even by the highly eclectic standards of Michael Winterbottom’s filmography, “The Trip” feels like an anomaly. Edited into a theatrical feature for stateside release after it aired in its six-part TV show incarnation on the BBC, it stars Rob Brydon and Steve Coogan as two characters who may or may not be the actors themselves, as they journey around the North English countryside, ostensibly on a tasting tour for The Observer newspaper. But while a bare minimum of foodie/travelogue stuff is included, the delight and the comedy of the film is in the interactions between these British comedy stalwarts —the competitive, one-upmanship of their relationship manifesting itself most hilariously in frequent extended bouts of impersonation— and also in the meta-collision between their onscreen and real-life personas. A remarkably clever project with more layers than a finely sauteed onion, it’s also oddly wise amid the laughs —a meditation on aging, talent and the transcience of fame that is even more pointedly melancholic in recent follow-up “The Trip to Italy.

23. “Team America: World Police” (2004)
Of all the things that could fuel a puppet-based feature-length comedy, perhaps righteous anger at U.S. foreign policy and the inanity of celebrity culture are not the first to spring to mind, but then “Team America” comes from those “South Park” guys Matt Stone and Trey Parker (co-written with Pam Brady), so perhaps it’s not quite as surprising after all. But even those of us who’ve never fully embraced “South Park” found “Team America” utterly brilliant and totally hilarious, perhaps because, like “Tropic Thunder,” it’s pointedness seems aimed at a celebratory culture of American military might that is largely regarded as sacrosant. Then again, with the daft puppet sex scenes, wildly un-PC portrayal of Kim Jong-Il, unshakeable Matt Damon impersonation and the bona fide brilliant songs (“I’m so Ronery” is a personal favorite), perhaps the more fratboy element of the audience took the “America, Fuck Yeah!” vibe at its face value. Which is itself the mark of the greatest satire: those who are its primary targets might not even recognize it as such.

22. “Elf” (2003)
As everything from “Santa Clause: The Movie” to “Jingle All The Way” to “Get Santa” will prove, it’s very, very hard to pull off the Christmas-themed movie. But if you get it right, as Jon Favreau undoubtedly did with “Elf,” your place is cinematic history is ensured (mainly by annual, ritualistic TV airings, but still…). The premise of the film reeked of cynical high-concept comedy of a kind that could have seen David Spade or Rob Schneider involved: Buddy (Will Ferrell) is a human raised as one of Santa’s helpers who leaves the North Pole in search of his real dad (James Caan), a workaholic publisher on the naughty list. But Ferrell works where so many others wouldn’t have —his turn is equal parts utter naivety and man-giant physicality (mixed with some unexpected and hilarious rage). And Favreau builds the film around him with a rare charm, from a genuinely sweet romantic sub-plot with cynic Zooey Deschanel to the Rankin-Bass winter wonderland. Making a movie that can sit alongside the holiday classic canon is a near-impossible task, but “Elf” pulled it off in style.

21. “In Bruges” (2008)
For anyone not acquainted with recent developments in English-language theater, their introduction not just to the work of Martin McDonough, but to the skewed, pitch black sensibility he shares with his brother John Michael (whose “The Guard” was also a contender for this list) would have been with Martin’s feature debut “In Bruges.” Based on his own intricately plotted script and spackled throughout with firecracker dialogue that manages to be quippy, lyrical and wildly profane all at once, “In Bruges” stars Irish national treasure Brendan Gleeson, gives Ralph Fiennes a surprising against-type turn as a cockney gangster and hands Colin Farrell one of his best roles to date as the callow hitman serving out his time in a Bruges that comes to stand for Purgatory. Constantly surprising but also confident enough to allow the chemistry of the stars to work its own unscripted magic, “In Bruges” is still Martin McDonough’s best and funniest film, though follow up “Seven Psychopaths” is a lot better than its reputation might suggest.

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