Penn played Woodchuck Todd in this hilarious 2010 comedy, who also happened to be Emma Stone's love interest in the film. Not too shabby.
Serena would definitely not approve of this outfit, but we definitely think this is Blake's best role ever. She showed us a whole new side of her (you know, the white trash, no fashion sense, slutty side) and got to work with Ben Affleck in the process, so double win.
Before we saw this movie we thought it would suck, but actually, it's great. Leighton plays the creepy college roomie role perfectly and we believed the whole time that she was actually a weirdo. And also, it's definitely a compliment that she got cast because she looks like her co-star, Minka Kelly.
Ed had a teeny tiny role in this flick, but he got to work with Leonardo Dicaprio in it. Leo, you guys! That's pretty huge.
Granted this movie happened way before 'Gossip Girl' did, but now Taylor's off making rock music with her band, The Pretty Reckless, and not doing much acting, so we had to choose this film as our fave. And also, she's just so cute here we can't take it.
If you thought Chace was hot as Nate Archibald, go see him in this movie, where he plays the best boyfriend slash baby daddy ever to Anna Kendrick. We die every time.