One Crazy Summer (1986)

After graduating from high school, art school hopeful Hoops McCann (John Cusack) struggles to complete his application to the Rhode Island School of Design. Resigning himself to a summer of boredom, McCann agrees to go along with his best friend, George Calamari (Joel Murray), on a family trip to Nantucket, Mass. But, after McCann and Calamari meet rocker-in-distress Cassandra (Demi Moore), it suddenly looks like it's going to be "one crazy summer."