It’s that time of year in movies when famous people start fishing for Oscars and George Clooney is one of them. The man is a true movie star, but which films has he been in that are truly great? I’m basing this not just on ‘how great is Clooney?’ but more on ‘how great is the movie as a whole?’ Spoiler alert: Leatherheads is not on this list, no matter what the criteria.

1. O Brother, Where Art Thou? (2000)
This one is easily in my top five movies of all time. Clooney stars as the Odysseus character in Joel and Ethan Cohen’s update of Homer’s epic poem. It’s a gorgeous film, earning an Oscar nomination for Best Cinematography in 2001, thought it lost to Crouching Tiger, Hidden Dragon. It also features some fantastic music and is genuinely funny. Add in supporting roles from John Goodman, Holly Hunter, and John Tuturro, and there is little about this movie that is great.

2. The Descendants (2011)Clooney’s most recent effort absolutely deserves a spot on this list, and may be the movie that gets him the Best Actor Oscar (he won Best Supporting Actor in 2005 for Syriana, but doesn’t yet have the leading man trophy). Playing father to his two daughters while his wife is in a coma, and ultimately finding himself dealing with his wife’s death, infidelity, and making a giant land deal on behalf of his extended family, Clooney has never been better. The film on the whole is incredibly moving and should be remembered for a long time to come as one of Clooney’s best achievements and could very well win a Best Picture Oscar.

3. Michael Clayton (2007)This is Clooney’s ‘guys wearing suits in back alleys speaking sternly into untraceable cell phones’ movie. Clooney stars as the title character, a clean-up lawyer (self-proclaimed “janitor”) shrouded in mystery who becomes responsible for fixing the situation when a lead litigator goes off the meds. One of Clooney’s darker roles, he’s great here and Tom Wilkinson is compelling as that unmedicated litigator. For an added bonus there are both Tilda Swinton and car explosions. You can’t go wrong.

4. Good Night and Good Luck (2005)A 50s era film following Edward R. Murrow (David Strathairn) reporting on the Communist-hating Senator Joe McCarthy, which Clooney directed and co-wrote with longtime writing/producing partner Grant Heslov. He also played the supporting role of Murrow’s producer, Fred Friendly. Good Night is smart and features other supporting roles from the always awesome Patricia Clarkson and Robert Downey Jr. Plus, who doesn’t love a well made historical movie?

5. Ocean’s 11 (2001)Ocean’s 11 might not quite belong in the top five over Up In the Air, but I’m putting it in anyway. There is absolutely nothing wrong with this movie. It’s funny, sweet, exciting, and who doesn’t love a well-made caper film? A remake of the 1960 Frank Sinatra, Dean Martin, Sammy Davis Jr. film of the same name, Ocean’s 11 let Clooney be very, very handsome in a lot of fancy suits. This is one of those that I can watch anytime it shows up on cable or the movie channels, and never tire of. Plus, it’s one of very few films from the 2000s in which Julia Roberts does not come off as the most annoying person on planet earth. So that’s impressive.

Honorable mentions:
Up In the Air (2009) – this one introduced non-Twilight fans to Anna Kendrick, for which we should all be thankful.
Syriana (2005) – Clooney won an Oscar for his Supporting role here, and as far as three hour long political thrillers go, this one doesn’t drag too much.
Out of Sight (1998) – just pretend Jennifer Lopez isn’t there and you’ll be fine.