Where you’ve seen him before: All over the place, especially in 2002, when he appeared in three Best Picture nominees, “Chicago,” “Gangs of New York,” and “The Hours.”
Why he deserves it: Small-town salesman Tim Lippe (Ed Helms) is warned about Reilly’s Dean Ziegler when he heads to Cedar Rapids for an insurance convention, and while it’s true that Dean is extensively vulgar and inappropriate, it turns out that he’s actually a pretty nice guy. Reilly is enthusiastic and funny, making the class clown three-dimensional and sympathetic.
Standout scene: Easily one of the most memorable moments of the film, pictured above, finds Dean swimming in nothing but his underwear in the hotel pool with a trash bucket lid on his head holding a drink in one hand and beeping like R2-D2. Especially in his drunkest moments, it’s hard not to like Dean.
Why he won’t get it: Reilly has had a busy year, appearing also in “Terri,” “Carnage,” and “We Need to Talk About Kevin.” Unfortunately, he won’t get any attention for any of those films. If a Fox Searchlight independent comedy from the first half of the year is going to earn any Oscar buzz, it’s “Win Win,” not “Cedar Rapids.” Reilly will have to settle for his well-deserved Independent Spirit Award Best Supporting Male nomination, where he contends against Albert Brooks, John Hawkes, Christopher Plummer, and Corey Stoll.
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