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In many ways, Out of Sight was not as huge a boost for Clooney as it was for the film's director, Soderbergh. The bespectacled director had been wallowing in self-absorbed projects for most of the 1990s, but when this fell into his lap, he brought the right amount of flash and style while letting Clooney and Lopez's natural chemistry do the rest. Audiences were convinced, though the film's box office wasn't as impressive as the film's impact is lasting. Though the term gets bandied about often (most recently, with regards to Mad Men star Jon Hamm), Out of Sight presented George Clooney with his first role akin to anything in the filmography of Cary Grant. His suavity isn't matched by the dimwit nature of his cohorts or the criminals around him, portrayed by the likes of Steve Zahn, Don Cheadle, and Albert Brooks, among others; however, the cool oozes off the screen here.

O Brother, Where Art Thou?

"Damn, we're in a tight spot!" Despite being the least faithful and most ridiculous version of Homer's classic epic The Odyssey, this 2000 Coen Brothers picture is the most fun and funny. Clooney is Ulysses Everett McGill, a recently escaped convict dragging along two other inmates, Pete and Delmar. He claims to hunt for treasure, but really just wants to get home to his loving wife, Penelope. Of course, once he finds her, he sees that Penelope has gotten involved with someone else, someone who is "bona fide". That won't stop Ulysses, to the point that he'll dress up as both a Ku Klux Klan member and as a bluegrass singer. I know, you're wondering how The Odyssey is connected at all, but can I point you in the direction of John Goodman, as the Cyclops as Bible salesman?

Yes, O Brother, Where Art Thou? is a bit of fun, but the bluegrass music is infectious, the cinematography by Roger Deakins is appropriately dusty-looking, and the screenplay is about as wordy and weird as something from the Coens gets (the scene where Goodman and Clooney first meet in a restaurant is deliciously verbose). Clooney proved here not that he could be a leading man, but that he had a sense of humor. In each of his collaborations with Joel and Ethan Coen, the filmmakers have sought to make fun of Clooney's public image; in O Brother, Where Art Thou?, they constantly make fun of his hair, by having Ulysses always look for some Dapper Dan pomade to get his hair just so. Nothing about this movie ever gets old, especially Clooney's frustrated charisma.

Ocean's Eleven/Twelve/Thirteen

Yes, I'm putting all three Ocean's movies here, from the 2001 remake to the 2007 threequel, all directed by Soderbergh. Most people, granted, aren't big fans of the second film, which certainly is deserving of the accusations that it's just an excuse for a lot of pretty people to hang out in fancy, palatial mansions. However, in the middle of all that hanging out is a brilliant, bizarre sequence in which Bruce Willis, playing himself, gets involved with Tess Ocean (Julia Roberts), who's pretending to be...Julia Roberts. The best running gag, to me, is how every one of the Ocean's gang dealing with Willis brags that they knew way before the end of The Sixth Sense what the twist would be.

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