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

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'The 40 Year Old Virgin' (2005)
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9. 'The 40 Year Old Virgin' (2005)

Judd Apatow had already made a name for himself with small-screen sketch comedy (he co-created The Ben Stiller Show), peerless cringe-comedy (The Larry Sander Show) and sensitive character-based comedy (R.I.P., Freaks and Geeks). For his big-screen directorial debut, he took a bit from all three and concocted what's become a modern-comic urtext: the heavily improvised, ensemble-cast manchild farce. A post-Daily Show/pre-The Office Steve Carell is the title character, a geek-culture lifer who's never had a real relationship; a crack team of supporting players including Romany Malco, Jane Lynch, Seth Rogen and Paul Rudd offer horrible romantic advice and off-the-cuff riffs about everything from soft rock to skin-mag stashes. (Seen today, the Rudd/Rogen volley of absurd "you're gay" playground taunts is somehow both a highlight and a low point.) The talent bench is deep here – blink and you'll miss Kat Dennings, Mindy Kaling, Jonah Hill and Kevin Hart in small parts – while Apatow's knack for connecting outrageous set pieces with a surprisingly overall sweetness would become his signature. But it starts here, and as everyone knows, you never forget your first time. DF

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