George Clooney is looking to score his second Oscar with his new romantic comedy Up in the Air. But only time will tell where this story will fit in on this list of his best and worst performances:

Top Five

5. Out of Sight: Clooney began his transition from TV doctor to major movie star by bringing the heat opposite Jennifer Lopez in this sexy cat-and-mouse romance between a charming diamond thief and a no-nonsense female U.S. Marshall.

4. O Brother, Where Art Thou?: Although Clooney brings his natural quick wit to nearly every role he plays, this Depression-set retelling of The Odyssey from the Coen brothers was the first time he truly showed off his impressive comic chops. It also continued his pattern of striking gold by playing convicted criminals.

3. Good Night and Good Luck: Clooney took a calculated risk that his fans would follow him into deeper waters when he stepped behind the camera to write, direct, and co-star in this black-and-white examination of the battle between 1950s CBS news anchor Edward R. Murrow and Communist witch-hunting Senator Joseph McCarthy. The risk paid off -- moviegoers started to appreciate the brains behind one of the most swoon-worthy faces in Hollywood.

2. Michael Clayton: Clooney showed off his serious side again and earned some of the best reviews of his career (not to mention a Best Actor Oscar nomination) for this legal thriller about a corporate "fixer" who risks his life by growing a conscience. Clayton proved that even in our age of blockbusters about children's toys, adult audiences still respond to intelligent dramas about real issues -- and that Clooney is the perfect actor to star in them.

1. Ocean's Eleven: It's not often that a remake becomes a classic in its own right, but that's exactly what happened when Clooney led an all-star ensemble on one of the most entertaining casino heists in Hollywood history. While it may not have landed him any awards, it was Clooney's performance as Danny Ocean that cemented his status as the Carey Grant of his generation.

Bottom Five

1. Intolerable Cruelty: After the inspired lunacy of O Brother, Clooney's second collaboration with the Coens was a let down. Audiences are still baffled at how such sexy and charming stars as Clooney and Catherine Zeta-Jones failed to find chemistry in this courtroom-set romantic comedy.

2. Solaris: Clooney has had some great successes in his frequent collaborations with director Steven Soderbergh. But many movie fans thought the two should be seperated after this baffling space oddity.

3. Ocean's Twelve: Clooney and Soderbergh took more heat for this bizarre and unfunny sequel to their hit heist comedy. Fan response was so bad, the third installment in the franchise felt like an apology to the moviegoers who sat through this one.

4. Leatherheads: There's nothing I can say about this stinker that wasn't already expressed (with much more hilarity) in Laremy's old-timey audio review which can be found and enjoyed here.

5. Batman and Robin In the movie world, there are few things that can kill a career faster than a bad superhero movie. It's a huge testament to Clooney's talent, charm, and overall coolness that he was able to make it in the movies after starring in what will forever be known as the Batman movie with the nipple suit.

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