Hoops McCann (John Cusack) is a recent high school graduate who failed to get a basketball scholarship, disappointing his parents.

Hoops hopes to be admitted to the Rhode Island School of Design, and must write and illustrate a love story for his application. He joins his friend George Calamari (Joel Murray), and George’s sister Squid (Kristen Goelz ), to spend the summer on the island of Nantucket, Massachusetts.

En route, they pick up a young rock singer named Cassandra Eldridge (Demi Moore); who is being chased by a motorcycle gang at the time. Once on the island, Hoops and George, along with George’s island friends the Stork twins and Ack-Ack Raymond, must help Cassandra save her grandfather’s house from the greedy Beckersted Family.

Along the way, Hoops must find a way to write his cartoon love story.