Gretchen Mol in American Loser (2007)

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A perpetual loser tries to turn his life around in American Loser (aka Trainwreck: My Life as an Idiot) (2007).  Based on a true story, this dramedy stars Sean William Scott as Jeff, a guy with a lot of problems. He’s a recovering alcoholic who has ADD, Tourette’s Syndrome, and a whole host of social deficiencies. He’s just been fired from his teaching job and is currently living at a bus stop. But when Jeff meets gorgeous gold-digger Lynn (Gretchen Mol), she (sk)inspires him to try to become a better man…even if she’s not such a good person herself.

Gretchen is fetchin’ when she puts on a sexy sheer nightie to have sex with our hero 15 minutes into the film. Now everyone’s a winner!