Van Wilder has been attending college for far too many years and is scared to graduate, but Van’s father eventually realizes what is going on. When he stops paying his son's tuition fees, Van must come up with the money if he wants to stay in college, so he and his friends come up with a great fund-raising idea – throwing parties. However, when the college magazine finds out and reporter Gwen is sent to do a story on Van Wilder, things get a little complicated.

Daniel Lugo, manager of the Sun Gym in 1990s Miami, decides that there is only one way to achieve his version of the American dream: extortion. To achieve his goal, he recruits musclemen Paul and Adrian as accomplices. After several failed attempts, they abduct rich businessman Victor Kershaw and convince him to sign over all his assets to them. But when Kershaw makes it out alive, authorities are reluctant to believe his story.

Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.

Derek and Simon meet two young women on the beach, but wind up in the emergency room.