Two down on their luck childhood friends struggle to figure out their lives. Ray (Chris Klein) a drummer in a rock and roll band, and Owen (Freddie Prinze Jr.) an aspiring film maker spend most of their time working menial jobs and drinking. When Owen's fiancé Lynn (Jamie-Lynn Sigler) breaks off their engagement he finds himself spiraling, and allows Ray to come along with him to a two bit film festival he has been invited to in Kansas. There Owen makes several attempts to patch up his relationship, while Ray scams them into a deluxe suite at the local Four Seasons hotel by posing as Wally Shawn's son (who happens to be receiving a lifetime achievement award) and generally causes a major ruckus. By the end, Owen decides to make some changes in their relationship and in his life.