The Sure Thing (1985)

Walter Gibson is a university freshman going through a dry spell. His old buddy arranges a "sure thing" for him in California. Gibson and his classmate Allison then take a long road trip out to California, and both foil each other's plans.

John Cusack makes an attempt to juggle 3 empty beer cans in a motel room. He was unsuccessful, perhaps because he was supposed to be drunk.