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Budding cartoonist Hoops (John Cusack) just finished high school, but still needs to turn in a project for acceptance into art school. So he goes to Nantucket with his pal, George (Joel Murray), for inspiration, which luckily comes in the form of pretty musician Cassandra (Demi Moore). Throw in a spoiled local bully, a sailing race and an evil developer's machinations to build a lobster restaurant, and you've got the makings of one crazy summer.