since he acts and directs, i'll cheat and use two. as far as acting goes, i'd say wristcutters. he met his best friend, the kind of humor is totally up his alley, and he got to hang out with tom waits. for directing, i'll say adventureland. superbad wasn't his baby as far as the actual story, but he worked long and hard on the script and was able to see it from the first few scribbles to the final product.
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