Cartoonist "Hoops" McCann (John Cusack) works on a scholarship application to the Rhode Island School of Design (RISD), before rushing off to attend his high school graduation ceremony. Hoops comes from a long-line of professional basketball players (his father and grandfather, great-grandfather, etc.) but was rejected for a sports scholarship to his college of choice due to his poor basketball performance on the school team of not scoring a single hoop. Hoops can't even throw a paper wad into a wastebasket from three feet away (a running gag used throughout the movie). At school, Hoops joins his best friend, George Calamari (Joel Murray), who persuades Hoops to spend two weeks partying on Nantucket Island before heading off to college. George stops to pick up his 10-year-old sister, Squid (Kristen Goelz), after school. She and her injured dog, Bosco, join George and Hoops for the trip to Nantucket after Squid shows that she does not tolerate any verbal abuse from others over her dog's ugly appearance. When two young girls make fun of Bosco and contort their faces, Squid slaps them on their backs and their faces stay that way. They both run off screaming. They stop for gas, and Hoops uses the restroom. A group of bikers led by Stain (John Matuszak) check the stalls looking for a woman named Cassandra (Demi Moore). As Stain demands his money, Hoops finds Cassandra's cash hidden in the towel dispenser, and throws the bills up in the air. He runs out, grabs Cassandra, and they jump into George's car. George speeds to the ferry, which is leaving the dock. George's car lands on the ferry deck, while the lead biker, Stain, falls into the bay (and getting little fish harpooned to his spiked pink-colored hairstyle). During the ferry ride, Cassandra informs them that she is visiting her grandfather, Mr. Eldridge, who lives on the island. When they arrive, she suggests they might meet again. George introduces Hoops to his friends, fraternal Stork twins Clay (Tom Villard) and Egg (Bobcat Goldthwait), two dim-witted local auto mechanics who are currently working as private security guards on a Hollywood film set for a movie titled 'Foam 2', a horror film about a dolphin with rabies menacing the community (a nod to the film series 'Jaws'). The group arrives at the home of George's grandparents. Grandma (Billie Bird) fusses over Squid while George's insane Uncle Frank (Bruce Wagner) has locked himself in a bedroom, listening obsessively to the local radio station, trying to win an on-air contest. The crotchety man tells his nephew and Hoops to scram. George and Hoops go to Target Beach, the local artillery range, and meet another friend, Ack Ack "Acky" Raymond (Curtis Armstrong), who collects mortar shells for his father, the gung-ho General Raymond (Joe Flaherty), the owner of the local guns and ammo store, who also heads up the local Scout troop. As they drive past a cemetery, Hoops notices Cassandra at her grandfather's funeral. Meanwhile, at the estate of the island's richest and most powerful family, the Beckersteds, Aguilla (Mark Metcalf) asks his spoiled son, Teddy (Matt Mulhern), if he is prepared to win this year's sailing regatta. Teddy has a new sailboat but the stakes are high. Old Man Beckersted (William Hickey), Teddy's wealthy grandfather, has vowed to disown Aguilla and Teddy if the young man does not win the trophy. Aguilla wants to use his father's resources to purchase the late Mr. Eldridge's property and build condominiums. However, his plan will be foiled if Cassandra raises $3,000 to pay Eldridge's back taxes. As Hoops walks with Cassandra on the beach, she explains her financial predicament. In addition, she worries that the friends her grandfather invited to live at the house will soon be homeless. Cassandra decides to sell some of her grandfather's furniture to raise money. Hoops draws cartoons to cheer her up (showing one of several animated sequences throughout the film of a "Lonely Rhino" searching for "Love" a blind cupid, while evading the evil and wealthy "Fuzzy Bunnies"). A few days later on the beach, Hoops works at his drawings until George suggests that the Stork twins entertain his friend. As they chat, Teddy's girl friend, Cookie Cambell (Kimberly Foster), asks Hoops, Clay, and Egg to help her launch her boyfriend's sailboat. Hoops declines Cookie's offer to go sailing but agrees to her offer to take in a movie at the local drive-in theater that evening. Later that evening at nightfall, Hoops learns that Cassandra has raised some money selling her grandfather's furniture. Cassandra invites him to the Dew Drop Inn to hear her play guitar, where she hopes to raise more money. Hoops promises to be there, but he has already made the movie date with Cookie. He tells his friends that he prefers to watch Cassandra perform, but Cookie shows up at the door, and he feels obligated to go to the movies with her. He asks the Storks to keep an eye on Teddy at his family's house in case he leaves to look for Cookie. At the Dew Drop Inn bar/restaurant, Cassandra takes the stage to play her acoustic guitar and sing, but there is hardly anyone in attendance. She also looks a little disappointed that Hoops is not there. On the film set of 'Foam 2', Egg takes over for his brother, watching the costume trailer and gets himself stuck in a Godzilla costume when he tries it on for a gag. When he realizes he has to be at the Beckerstead's party at 8:00 pm to watch Teddy, he is forced to go there in the costume. At the drive-in theater, Hoops buys snacks, and Teddy's friend, Ty (Jeremy Piven), notices that Hoops is with Cookie. Ty telephones his friend and reports that Cookie is on a date with Hoops. The news sends Teddy into a jealous rage. Elsewhere, Grandma takes Squid on a drive into town for dinner. While at a gas station, the two attendants make fun of Squid's dog, prompting Squid to roll up her car window and trap their neckties. Grandma drives off, dragging them down the road. At the Beckersted estate, Egg (still stuck in his Godzilla costume) hides in the bushes where a fundraiser is being held to raise money for the condo developments on the Elderidge property, and some Japanese investors are in attendance. When Old Man Beckersted throws a lit cigar away, it lands in Egg's Godzilla mouth. Egg goes crazy and crashes the party with smoke billowing out of his costume's mouth and stomps on the condo development models (resembling a Japanese monster movie of Godzilla stomping on city buildings) before running away into the night. Back at the drive in theater, Cookie is bored, and suggests that they go to "the Point" and look at the moon. At the Point, General Raymond delivers a rousing speech to his Boy Scout troop about how their overnight retreat is a perfect opportunity to practice their rescue skills. Just then, Hoops slips and falls, and the scouts descend and wrap him in bandages like a mummy. The scouts chase after Cookie, but she runs away and Teddy picks her up in his car, Cookie unfairly blaming Hoops and his friends for her terrified state. George rescues Hoops, and they drive to the Dew Drop Inn, but it is closed for it is after 11:00pm. Egg also arrives still dressed in his Godzilla costume as well as Acky and Clay, and they all help Egg out of the costume. When Teddy arrives with his friends and threatens to beat up Hoops, Cassandra steps in and challenges Teddy to compete against Hoops in a series of free-throw basketball shots (unaware that Hoops is terrible at basketball). Using Ack Ack as a makeshift "basket", Teddy makes every shot and Hoops misses every shot. Teddy is eager to rough up Hoops, but Cassandra sprays mace so that her new friends can escape. Hoops thanks her, and apologizes for missing her performance. A few days later, Hoops sees Cassandra at the beach, and offers to use his animation skills to help her fund raise. He creates an animated advertisement for Cassandra's performance, and shows it at the drive-in. He and his friends also hand out concert fliers in town. When Aguilla Beckersted realizes that Cassandra might raise enough money to save her grandfather's property, he enlists Teddy to prevent her from performing. Hoops and his friends fight back by pouring barrels of live lobsters into the Beckersted swimming pool. When Teddy goes for a swim with Cookie, the lobsters attack them both. Cassandra's concert is a success, but when she shows up to pay the tax bill, the meek banker explains that he already sold the mortgage to Old Man Beckersted. In revenge, Aguilla reveals more of his ruthlessness when he kicks and severely injures Squid's dog, who has to go to the animal hospital (staffed mostly by animals). Cassandra is ready to give up, but Acky suggests they enter and win the regatta by beating Teddy. The friends work to repair a shoddy boat, and Cassandra persuades Hoops to be captain. As they finish the boat, they realize they don't have a very powerful engine. Clay shows up with Teddy's Ferrari to have it serviced at their garage. Egg notices that Clay has a black eye given to him by Teddy. Egg becomes enraged, grabs a chainsaw and approaches Teddy's Ferrari... Race day arrives and most people laugh at Hoops' team and their boat, which looks silly next to the higher end sloops. The race begins with each team rowing out of the harbor. When they start to fall behind, George eggs Egg on with negative news about his favorite wrestling star and they begin to make up some distance. Teddy's team pulls way out in front when the rest of the boats hoist their sails for the next leg of the run. After a few miles, Aguilla Beckersted appears aboard Teddy's boat and sabotages Hoops' team by cutting their lanyard line with an arrow from a cross bow. Unable to thread the rope at the top of the mast, Hoops uses a small weight, and on a million-to-one shot, throws the small bearer ball through the hoop at the top (thus ending his curse at not being able to score any hoops). As Hoops, George, Acky, Clay and Egg sail on, Aguilla aims another arrow to put a hole in Hoops' craft, when the mechanical dolphin from 'Foam 2', powered by Squid, rams into the boat. Aguilla falls overboard where the mechanical dolphin "eats" him alive. The top hatch pops open and Squid cheerfully waves. In the last lap, the racers retract the sails and engage the boats' engines. Teddy leaves his father in the water and speeds toward the finish. Hoops' team all don anti-aircraft helmets and blow the boat's rear "hatch", revealing the engine from Teddy's Ferarri, installed by the Stork twins after Egg's rampage. Hoops and his friends speed to victory (giving 'the finger' to Teddy, Ty and the rest of his snobby friends). Afterward, Hoops offers Teddy the trophy in exchange for the Eldridge house. However, Old Man Beckersted, impressed with the novice team's effort, informs Cassandra that he is returning the Eldridge property to her and there will be no real estate development. Hoops and Cassandra celebrate and kiss for the first time. Also, Squid's dog is alive and returns to her... after giving birth to a litter of puppies at the animal hospital. In the final scene sometime later, George's uncle Frank finally wins the radio call-in contest for $1 million, but his phone gets disconnected before he can tell the DJ his name and his prize is given away to someone else; he snaps and promptly uses a rocket launcher to fire a guided missile to blow up the radio station. The Stork twins arrive in their tow truck and head to the fiery remains to roast marshmallows.
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