Harvard Man (2000)

When a Harvard student who plays on the basketball teams finds himself in need of $100,000 to save his parent’s home he agrees to rig a game for his girlfriend’s mobster father. It seems like a fool proof plan, but things don’t go so smoothly.

Adrian Grenier plays the not-so-lucky basketball player who knows how to score on the court and in the bedroom. He hooks up with a few different women here. During one encounter his pants are around his ankles as he drives his main bone home while she sits on the edge of the couch. We really only see his legs here, but later as he gets on top of his girlfriend and pumps away his sweet seat is on fully display. His ass looks so good he will have you gathering up an Entourage for a party in your pants. We also see him shirtless and in his basketball uniform. It is a Skindeforce kind of performance from Adrian.