If at first you don't succeed, try, try again. We hear it all the time, but George Clooney is living proof that perseverance pays off: Despite the inauspicious beginnings of a career that threatened to pigeonhole him as a Ted McGinley-style supporting player on fading sitcoms, he's risen to the ranks of Hollywood's highest-paid actors, and has appeared in some of the last decade's most critically and commercially successful films. This fall, Clooney surfaces in three major releases: Wes Anderson's Fantastic Mr. Fox, Jason Reitman's Up in the Air, and The Men Who Stare at Goats, opening this weekend. If that kind of star power doesn't deserve the Total Recall treatment, what does?

72%

Fresh

10. Syriana

It's always fashionable to lament the lack of imagination and depth in mainstream Hollywood fare -- and, quite often, it's easy to understand why. But every so often, someone manages to slip something demanding into the release schedule. Case in point: 2007's Syriana, a twisty political thriller that takes an impossibly intricate script (written by Stephen Gaghan, also making his directorial debut), adds a top-notch ensemble cast, and wraps the whole thing up in 128 minutes of espionage and intrigue with equal parts visceral and intellectual appeal. As Robert Barnes, the CIA operative who becomes an unwilling expert in the painful side effects of shifting Middle Eastern alliances, Clooney was only one part of a cast that included Matt Damon, Jeffrey Wright, Chris Cooper, and William Hurt -- but as one of the film's executive producers, he was a crucial element of a movie that overcame its heady themes to earn almost $100 million worldwide. Lauding Syriana as "a film that treats its audience as adults," Channel 4 Film's James Mottram wrote, "this is an extremely rewarding work that handsomely pays off the concentration required to watch it."

75%

Fresh

9. Intolerable Cruelty

What do you get when you cross the Coen brothers with the tired old romantic comedy genre? 2003's Intolerable Cruelty, in which the directing/screenwriting duo turns its deep black humor on the sexy screwball laffers of the '30s, putting Clooney and Catherine Zeta-Jones in the center of a story with enough twists, turns, and double-crosses for a hundred Kate Hudson movies. The plot, which pits a brilliant but bored divorce attorney (Clooney) in a battle of the sexes against one of his former clients' spouses (Zeta-Jones), isn't terribly original, but the script has plenty of zingers -- and the leads threw enough sparks to charm even many of the critics who came away from Cruelty disappointed with the Coens' surprisingly mainstream shift. In the words of the Globe and Mail's Liam Lacey, "If Intolerable Cruelty establishes one thing, it's that George Clooney is the closest thing that contemporary Hollywood has to an old-fashioned matinee idol."

77%

Fresh

8. Burn After Reading

After tunneling deep into the dark underbelly of human nature with their adaptation of Cormac McCarthy's No Country for Old Men, the Coen brothers decided to beat a lighthearted retreat for its follow-up, 2008's Burn After Reading -- and, in the process, reunite with one of their favorite leading men. For his third project with the Coens, Clooney took on the role of Harry Pfarrer, a Treasury agent whose romantic exploits are as unfortunate as they are prolific. Conducting an adulterous affair with Katie Cox (Tilda Swinton) while simultaneously fooling around with Linda Litzke (Frances McDormand), Pfarrer is hilariously unaware that both women are involved in some way in the botched extortion scheme that's about to send his life spinning off its axis. Though Burn represented a substantial critical comedown for the Coens after the award-hogging No Country, it was a hit with most scribes, including Armond White of the New York Press, who wrote, "Lesser artists would have followed a critical smash like No Country with another noir, courting audience favor through familiarity. But Burn After Reading, though shocking, is simply the flipside of the Coens' existential dread."

77%

Fresh

7. O Brother, Where Art Thou?

In lesser hands, a broadly comic, Depression-era update on the Odyssey could have been the most embarrassing thing George Clooney would be associated with since Return of the Killer Tomatoes, but the Coen brothers made it work -- and how: Between its $71 million gross and a soundtrack so popular it spawned its own documentary, O Brother, Where Art Thou? was one of 2000's cinematic sensations (albeit one whose impact was more cultural than financial; ranking 60th on the annual box office results, it was just a shade less successful than Dude, Where's My Car?). Despite some South Park vocal cameos and his noteworthy late-series run on The Facts of Life, Clooney's comedic gift remained largely undiscovered until the Coens turned him loose to ham it up as Ulysses Everett McGill, the fast-talking escaped con whose quest for ill-gotten gains leads him to an accidental career as a member of an old-time music trio. Sound like a loopy plot? Well, toss in some Klansmen, a floating cow, and John Goodman in an eyepatch, and you can understand why Eugene Novikov of Film Blather said "O Brother, Where Art Thou? is the Being John Malkovich of the year 2000," adding, "The most remarkable thing about it is just how any sane studio executive agreed to back it."

78%

Fresh

6. Confessions of a Dangerous Mind

It's one of Hollywood's most oft-repeated jokes that what actors really want to do is direct -- but when they do get their first shot behind the cameras, very few actors take the opportunity to create something as wonderfully strange as Confessions of a Dangerous Mind. Adapted by Charlie Kaufman from the Chuck Barris memoir that may or may not have included giant chunks of complete fiction, Confessions introduces the viewer to a world in which noted television producer Barris (played by Sam Rockwell) is recruited by a CIA agent (Clooney) to carry out secret political assassinations -- and it gets even weirder from there. Arriving in theaters years after Barris' TV heyday, Confessions never really had a prayer of catching on at the box office, but it -- and Clooney -- earned the admiration of critics like Glenn Lovell of the San Jose Mercury News, who wrote, "Clooney, who on the basis of this movie has a big career ahead of him behind the camera, demonstrates a real flair for visual comedy."