Description
Hoops McCann, a recent high school graduate, fails to get a basketball scholarship, disappointing his parents. He 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 friends, siblings George and Squid Calamari, to spend the summer on the island of Nantucket, Massachusetts.
En route, they pick up a young rock singer named Cassandra Eldridge, who is pursued by a motorcycle gang at the time. Once on the island, Hoops and George, along with twin brothers Egg and Clay Stork and outcast Ack-Ack Raymond, must help Cassandra save her grandfather's house from the greedy Beckersted Family (led by the callous Aguilla). Along the way, Hoops must find a way to write his cartoon love story.
Hoops runs afoul of Teddy Beckersted and his neglected girlfriend, Cookie. She secretly offers Hoops a date, and he is persuaded to go out with her even though he had promised to appear at Cassandra's first musical performance (which turns out to be sparsely attended). Hoops and Cookie go to a drive-in that night, where Teddy's friend Ty sees them and notifies Teddy.
Meanwhile, Egg gets stuck in a Godzilla costume and causes havoc at Beckersted's promotional party for the Beckersted Estates (which would be located at the spot of Cassandra's grandfather's house). Hoops, George, Egg and Ack-Ack run into Teddy and his friends. As he threatens them, Cassandra appears and offers an impromptu basketball challenge between him and Hoops; Teddy dominates and Hoops fails. After spraying Teddy and his friends with mace, Cassandra is upset that Hoops did not appear for her performance and lied that he was a good basketball player.
In an effort to make it up to her, Hoops and his friends promote her next performance, which turns out to be a big success, and Cassandra forgives him. However, Aguilla immediately forecloses on the house before it can be saved. Ack-Ack proposes they take part in the local regatta, despite Hoops' fear of the water. Nevertheless, they find and renovate an old boat to use. The regatta starts with the teams using paddles, then sails. Teddy's team recklessly injures a member of one team and Ack-Ack jumps into the water to save him. Aguilla, having stowed away on Teddy's boat, sabotages Hoops' sail with his crossbow. To repair the mast, Hoops successfully shoots the new guy line into the mast and they continue onward. Before Aguilla could shoot the mast again, he is thrown overboard by Squid operating a mechanical dolphin from a nearby movie set, as retaliation for when he kicked her beloved dog earlier. When the teams use the motors, Hoops and his team win after using Teddy's car engine as their motor.
Hoops and his friends celebrate their victory—they are awarded the prize, Squid's dog turns out okay (after giving birth to puppies), George hooks up with Cookie, and Ack-Ack wins his stern father's approval for his heroics. Despite winning, Hoops offers the trophy to Teddy if he spares Cassandra's house, but Teddy immediately backs out on his promise. However, Old Man Beckersted (father of Aguilla and grandfather of Teddy) gives back the trophy and spares Cassandra's house, stating he wasn't going to "put a dime" in the Beckersted Estates; he then drags Teddy away by his ear.
With the prize returned and the house spared, Hoops and Cassandra kiss, and she inspires a love story for his application. In the final scene, George's uncle Frank finally wins a $1 million prize from a radio contest (having been driven insane every summer for trying to win), but his phone gets disconnected and his prize is given away to someone else; he snaps and promptly uses a rocket launcher to blow up the radio station, and shortly thereafter the Stork twins arrive and head to the still-burning station to roast marshmallows.
