Harvard Man (2000)

An Ivy League basketball star isn't smart enough to avoid getting caught up in a point shaving scheme in Harvard alum James Toback's Harvard Man (2001). Adrian Grenier plays Alan Jensen, Kansas boy turned star point guard for the Harvard Crimson who is in dire need of 100K after his parent's house gets destroyed by a tornado. There was no NIL in 2001, so the odds of Alan making that kind of money the legal way is precisely nil. Luckily, his girlfriend Cindy (Sarah Michelle Gellar) was raised by the mob and decides he can just throw a game, her dad's buddies Teddy (Eric Stoltz) and Kelly Morgan (Rebecca Gayheart) can make a ton of money betting on it, and when they go to collect the cash, they can throw 100 G's his way. The problem is, those mobsters are actually FBI agents! Alan will end up throwing the game and taking some LSD, only to get saved by his professor sidepiece Chesney (Joey Lauren Adams) who is banging both Teddy and Morgan and can keep them off his back. 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, but he's not the only dude in Harvard Yard who could make you super hard. A jacked hottie, Scottie Epstein is gorgeous as he throws the football around by the pool. He looks incredible without his shirt on, even if his throwing motion is embarrassingly bad. Even the GILFy Gianni Russo is erotic standing waist deep in the swimming pool. You'll want to get in the pants of that smartypants watching Harvard Man!