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50 Greatest Comedies of the 21st Century

From rom-coms to raunch-coms, ‘Anchorman’ to ‘Wet Hot American Summer’ – the funniest movies of the new millennium so far

50 greatest comedies

What’s so funny? If you’re talking about screen comedy in the 21st century, the answer is easy: bumbling manchildren, the more boorish and clueless and stuck in their stunted adolescence, the better. Talking foxes, Huey Lewis-loving serial killers, world-saving marionettes, foul-mouthed political fixers and boisterous bridesmaids – all great as well. German father-daughter duos and goofy stoners? Bring ’em on! Headbanging teachers and backstabbing bureaucrats? Yes, we’ll take them too.

Since the turn of the century, we’ve giggled at the poignant and the perverse, rom-coms and raunch-coms, new-and-improved takes on singular comic types and loose, highly improvised ensemble pieces that spread the spotlight around. Some of these movies have been gently witty, while others have displayed all of the subtlety of a dose of Sex Panther cologne. But they’ve all consistently cracked us up, in a near–two-decade span in which – let’s be honest – we’ve need a laugh or two. Or three. Or a dozen.

After a number of heated arguments and lots of name-calling and the occasional chaotic pie fight, we’ve narrowed down our choices for the greatest comedies of the 21st century. Culling this down to a mere 50 entries was a tough call – humor is a seriously subjective topic, and every one of our 19 writers weighing in had their own idea of what constitutes “hilarious.” But this list represents the best cross-section of screen comedy of our still young millennium, a collection that runs the gamut from droll to bladder-loosening. Given the high possibility of sidesplitting, you may wanna have a medical professional on hand. And don’t forget to stay classy, San Diego.

'Superbad' (2007)

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‘Superbad’ (2007)

Taking a page out of their mentor Judd Apatow’s book, cowriters/BFFs Seth Rogen and Evan Goldberg went back to their youth and crafted a teen comedy with dick drawings (dozens of ’em), dirty jokes … and a heart and soul. Yes, it’s about two high-school dudes (Jonah Hill and Michael Cera) trying to get laid, and the antics involving a party gone out of bounds, period blood, a character named “McLovin’,” kooky cops and copious alcohol consumption that ensue – so far, so grossout. But underneath all the teen-boys-are-genuinely-disgusting humor and Porkys-style shenanigans is
a thread of deep-seated insecurity, stemming from the fact that
adulthood is fast approaching and soon these close friends will be heading off to different
colleges. By that time that talking about “p in vagee” gives way to an affectionate “boop” at the end, you’re smitten. All this, plus a near-perfect turn from Emma Stone. Super, indeed. EZ

'24 Hour Party People' (2002)

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’24 Hour Party People’ (2002)

Thanks to his signature character Alan Partridge, comedian Steve Coogan is an expert at playing a legend in his own mind. But what if the legend lived up to the hype? That’s the wild sex-drugs-and-rock & roll thrill behind this stranger-than-fiction true(ish) story of influential music-biz pioneer Tony Wilson – a blowhard TV-news cornball turned record-label founder and nightclub impresario who brought Joy Division, New Order and Happy Mondays to the world before going broke. Coogan and his frequent collaborator, director Michael Winterbottom, chronicle Wilson’s rise and fall with fourth-wall-breaking bravura and good-natured glee. STC

'Frances Ha' (2012)

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‘Frances Ha’ (2012)

Who likes understated, black-and-white slice-of-life dramedies that pop with colorful humor and awkward comments? Twentysomething angst doesn’t get any better or more comically bittersweet than this cracked character study from director Noah Baumbach and cowriter/star Great Gerwig, in which the eponymous heroine aimlessly pings from downtown Manhattan to Northern California, Paris to Vassar – yet really just ends up going endlessly in circles. There are plenty of slapstick comedy moments as Gerwig’s lost soul busts up old friendships and burn bridges, but this minor gem thrives on the laughter bred from cringe-worthy moments. “I’m embarrassed. I’m not a real person yet.” Neither are we, Frances. Neither are we. KYK