John Cusack plays a record store owner who passes the time by making "top five" lists. He has top five reasons for everything and is constantly coming up with different topics. He spends most of the movie talking into the camera explaining these lists to us
The film opens with him being dumped by his girlfriend Laura. He tells her, and us, that she isn't even in is top five breakups. We then see little scenes from his earlier five breakups. The more he thinks about Laura, the higher up the list she becomes. She has left him for Tim Robbins, a self help lecturer that lived upstairs.
Cusack's 2 employees know everything about every song. Jack Black (of Tenacious D fame) plays Barry, his employee that is very rude to customers that he deems not worthy of certain music. It's a wonder that the store stays in business.
Cusack is always looking for that fantasy girl. It's amazing that he can always get them. These vary from Catherine Zeta-Jones to Lisa Bonet. He's about to win over a new music writer when he finally starts to come to his senses.
He has got to start looking towards the future. He signs a couple of "skateboarders" that have a band are actually pretty good. He is going to finance a CD for them. The fact that he is moving forward, impresses Laura. She slowly starts coming back to him.
Finally Laura throws a "CD Party" to debut the kid's new CD. Barry opens the show by belting out an old Marvin Gaye tune and is awesome, to the amazement of everyone.
Cusack proposes to Laura and everything is wonderful again.
Spoiled by: The Movie Spoiler