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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."