Harvard Man is an interesting portrait of a film gone awry. Somewhere within its story, writer/director James Toback (Black and White, Love in Paris) has something interesting to say about something, but he never gets around to it. Instead, he loses himself in soap opera-like plot twists, titillating sexual antics, and a spectacular case of miscasting. The story centers on Alan Jensen (Adrian Grenier, Hart's War, A.I.), a basketball player at Harvard. He is a typical college student, the typical kind that dabbles in illegal substances, dates the daughter of a mafia boss, and sleeps with a professor on the side. Jensen is also looking for some deep inner truth. He is on a quest to discover who he really is, and three cubes of LSD may help him do that.

Jensen in the star point guard for his team. When a natural disaster in Kansas destroys his parents' house, he realizes he needs to do something to help them rebuild. They have no insurance, and cannot secure a loan, so Jensen asks his girlfriend Cindy Bandolini (Sarah Michelle Gellar, Scooby-Doo, Cruel Intentions) to ask her father for a loan. Her father agrees, with the caveat that Jensen throw his next game. Jensen is basically a good guy, so this throws him into a moral crisis. He begins to rationalize his way out of it; the game is not important in the bigger scheme of things. If he throws the game, nobody is hurt, yet his parents now have money for a house. At this point, Harvard Man begins is quick spiral downward.

Bandolini wants to play the odds for her own gain, so she places a bet with Teddy Carter (Eric Stolz, The House of Mirth, The Simian Line) and his assistant Kelly (Rebecca Gayheart, Urban Legends: Final Cut, Shadow Hours). Teddy works for Bandolini's father, but she doesn't want her father to know. What nobody knows is that Carter works for the FBI, and is building a case against the Bandolinis. What most people also don't know is that both Teddy and Kelly are sleeping with Chesny Cort (Joey Lauren Adams, Jay and Silent Bob Strike Back, Dr. Dolittle 2), the same professor that Jensen is sleeping with. Teddy sets his sights on Jensen, who decides to take the LSD (all three cubes) to heighten his awareness. Harvard Man changes into a dangerous game where each person is trying to outsmart the other.

The bulk of the latter portion of the film is Grenier running around on a horrible trip, while Gellar freaks out and Stolz acts annoyed. The main problem is that Grenier, Gellar, and Adams do not fit their roles. None of them are convincing. Grenier is too short and his build is wrong, Gellar cannot handle the subtleties of her role correctly and comes off as lame, like Adams' performance as a professor. The combination of the three is not good. The overall effect is one of shock - what is Toback thinking? Whatever Toback wanted to say about life or the meaning of one's existence loses itself in his attempts at what possibly may be humor. It is distracting and lends nothing meaningful to the story. By the end of Harvard Man, it feels like the viewer went on a bad trip.