One Crazy Summer

As "Hoops" McCann (John Cusack), a talented but hapless cartoonist, frantically works on his scholarship application to the Rhode Island School of Design (RISD), time is running out. With the clock ticking down, Hoops must put aside his academic aspirations and attend his high school graduation ceremony, marking a bittersweet milestone in his journey. Despite hailing from a long line of accomplished basketball players - a legacy he's struggled to live up to - Hoops' own athletic endeavors have been met with disappointment, with a sports scholarship out of reach due to his woeful performance on the court. His lack of coordination is so pronounced that even attempting to toss a paper wad into a nearby wastebasket from just three feet away proves an impossible feat.

Meanwhile, Hoops' best friend, George Calamari (Joel Murray), has other plans in store for their summer break. Convinced they can party the night away on Nantucket Island, George convinces Hoops to join him for a two-week escapade. Their impromptu adventure takes an unexpected turn when George stops to pick up his 10-year-old sister, Squid (Kristen Goelz), from school, accompanied by her loyal yet misshapen canine companion, Bosco. When two young girls cruelly mock the dog's appearance, Squid steps in to defend her furry friend, leaving the bullies with a lasting - and rather comical - facial contortion.

As they fuel up for their road trip, Hoops takes a quick restroom break, only to stumble upon a hidden cache of cash belonging to Cassandra (Demi Moore), stashed away in the towel dispenser. With Stain (John Matuszak) and his gang of bikers hot on their heels, demanding to know the whereabouts of Cassandra, Hoops seizes the opportunity to throw caution - and the bills - to the wind. As chaos ensues, George speeds off to catch the departing ferry, with Hoops and Cassandra in tow, while Stain takes an impromptu swim in the bay, inadvertently becoming the main attraction for a school of hungry fish.

As the ferry ride unwinds, Cassandra reveals her plans to visit her grandfather, Mr. Eldridge, who resides on the island. Upon arrival, she hints at the possibility of a future encounter with George and Hoops. Upon arriving at the grandparents' abode, George introduces Hoops to his eccentric friends - the Stork twins, Clay (Tom Villard) and Egg (Bobcat Goldthwait), two lovably dim-witted auto mechanics who moonlight as private security guards on a Hollywood film set for a horror movie titled 'Foam 2', which revolves around a rabid dolphin menacing the community. The group arrives at the residence of George's grandparents, where Grandma (Billie Bird) fusses over Squid while Uncle Frank (Bruce Wagner), consumed by madness and an insatiable need for radio validation, locks himself away in his bedroom, frantically tuning into the local airwaves in a bid to win a coveted on-air contest. This crotchety individual promptly dispatches George and Hoops with a curt "scram".

As the sun dips below the horizon on the beach, Hoops becomes absorbed in his drawings as George suggests the Stork twins entertain their friend. Meanwhile, Teddy's girlfriend, Cookie Campbell (Kimberly Foster), approaches Hoops and requests assistance from him, Clay, and Egg to help launch her boyfriend's sailboat. Initially, Hoops declines her offer for a sailing adventure but agrees to accompany her to the local drive-in theater that evening instead.

Later that night, as the stars begin to twinkle in the sky, Hoops discovers that Cassandra has successfully raised some funds by selling her grandfather's furniture. Inviting him to join her at the Dew Drop Inn, she hopes to raise even more money through her guitar playing. Hoops promises to attend but has already made a commitment with Cookie to watch a movie at the drive-in. Feeling torn, he confides in his friends, revealing his true preference for Cassandra's performance over the film date with Cookie. However, just as he's about to share this revelation, Cookie arrives at the doorstep, and Hoops feels obligated to honor their plans.

As Hoops navigates the evening, he asks the Storks to keep an eye on Teddy at his family's residence in case he decides to venture out in search of Cookie. Unbeknownst to Hoops, Egg takes over for his brother, donning a Godzilla costume while working on the set of 'Foam 2'. Realizing he needs to attend the Beckerstead party by 8:00 pm to watch Teddy, Egg is forced to make an appearance at the gathering in his oversized suit.

Meanwhile, Cookie grows restless and suggests that they head "the Point" to gaze up at the moon. Elsewhere, Grandma embarks on a drive into town with Squid for dinner. While stopping at a gas station, two attendants mock Squid's dog, prompting Squid to roll up her window, trapping their neckties. As she drives away, the attendants are left clinging to the road.

At the Beckerstead estate, Egg (still stuck in his Godzilla costume) finds refuge in the bushes as a fundraiser is held to raise funds for the condo developments on the Elderidge property. Japanese investors are also in attendance. Back at the drive-in, Hoops purchases snacks and attracts the attention of Ty (Jeremy Piven), Teddy's friend. Upon learning that Hoops is on a date with Cookie, Ty reports this news to his friend over the phone, sending Teddy into a jealous frenzy as a result.

As Old Man Beckersted carelessly flicks away a lit cigar, it lands in Egg's gaping maw, sending him into a frenzy. The unsuspecting partygoer's costume erupts in a cloud of smoke, and he stomps on the meticulously crafted condo models, leaving them in ruins (a scene eerily reminiscent of Godzilla's iconic destruction of Tokyo). As chaos ensues, Egg makes a hasty retreat into the night.

Meanwhile, General Raymond stands before his Boy Scout troop, passionately urging them to seize this overnight retreat as an opportunity to hone their rescue skills. However, their camaraderie is disrupted when Hoops takes an unfortunate tumble, prompting the scouts to rush to his aid and wrap him in bandages like a mummy. The troop's enthusiasm soon turns to chaos as Cookie flees the scene, chased by her friends, only to be scooped up by Teddy, who is quick to assign blame to Hoops for her distress. George swoops in to rescue his friend, and they embark on a journey to the Dew Drop Inn, but find it closed due to the late hour.

As if fate had conspired against them, Egg arrives at the inn, still clad in his Godzilla costume, accompanied by Acky and Clay. Together, they help Egg out of his elaborate attire, only for Teddy to arrive with his cohorts, spoiling for a confrontation with Hoops. Cassandra intervenes, proposing a series of free-throw basketball shots as a means to settle their differences, unaware that Hoops is woefully inept at the sport. Using Ack Ack as an impromptu "basket," Teddy effortlessly sinks shot after shot, while Hoops misses each attempt. As Teddy prepares to unleash his aggression on Hoops, Cassandra sprays mace, allowing her new friends to escape unscathed. Hoops expresses gratitude and apologizes for missing Cassandra's performance.

Days later, Hoops encounters Cassandra at the beach, offering to leverage his animation skills to aid her fundraising efforts. He crafts an animated advertisement promoting her upcoming show, screening it at a local drive-in, and he and his friends distribute concert fliers throughout town. As Aguilla Beckersted becomes aware that Cassandra's fundraising might prove sufficient to save her grandfather's property, he enlists Teddy to thwart her performance. Hoops and his friends retaliate by dumping barrels of wriggling lobsters into the Beckersted family swimming pool. When Teddy takes a leisurely dip with Cookie, the crustaceans turn their attention on the unsuspecting duo.

As Cassandra's euphoric concert tour wraps up, she's confronted with a harsh reality when she arrives to settle her tax bill: the meek banker reveals that he's already sold the mortgage to the ruthless Old Man Beckersted. In a shocking display of brutality, Aguilla unleashes his wrath by viciously attacking Squid's beloved dog, sending it scrambling for medical attention at the animal hospital, where a team of furry professionals springs into action.

Cassandra is on the brink of surrender, but Acky persuades her to channel their frustration into a new challenge: winning the regatta by outmaneuvering Teddy. With Hoops at the helm and Clay's garage providing the necessary tools, the friends laboriously restore a rickety boat, only to realize they're woefully underpowered. Just as they finish the vessel, Clay appears with Teddy's prized Ferrari, which he brings in for a tune-up. Egg notices Teddy's latest victim - a battered and bruised Clay - and his anger boils over. He seizes a chainsaw, eyes fixed on Teddy's sleek machine...

The day of reckoning arrives, and most spectators are amused by Hoops' team's makeshift boat, which looks laughable alongside the high-performance sloops. The competition begins with each squad rowing out of the harbor, their oars dipping in unison. As they fall behind, George egging Egg on with negative updates about his favorite wrestler fuels a newfound determination. Teddy's team pulls ahead as the other boats raise their sails for the next leg of the journey.

But just when all hope seems lost, Aguilla Beckersted materializes aboard Teddy's boat and sabotages Hoops' team by severing their lanyard line with an arrow from his crossbow. Stranded and unable to repair the damage, Hoops resorts to a Hail Mary, using a small weight to guide a ball through the hoop at the top of the mast, shattering the curse that had plagued him. As Hoops, George, Acky, Clay, and Egg continue their journey, Aguilla readies another arrow to sink their craft when Squid's mechanical dolphin, fueled by 'Foam 2', bursts forth from the depths, slamming into the boat and sending Aguilla tumbling overboard. The mechanical sea creature then "consumes" him, its hatch opening to reveal a beaming Squid waving triumphantly.

As the competition reaches its thrilling conclusion, the sailors abandon their sailboats' canvas sheets and ignite the powerful engines, propelling their vessels forward with unbridled enthusiasm. Teddy leaves his father stranded in the water, choosing instead to accelerate towards the finish line at breakneck speed. Meanwhile, Hoops and his team don makeshift anti-aircraft gear and expertly blow open the rear compartment of their boat, revealing the sleek engine installed by the cunning Stork twins following Egg's rampage. With a triumphant flourish, Hoops and his friends claim victory, flipping a defiant middle finger to Teddy, Ty, and the rest of the snobbish elite. In a stunning turn of events, Hoops offers Teddy the coveted trophy in exchange for the long-sought Eldridge estate, only to have Old Man Beckersted unexpectedly declare that Cassandra will retain ownership of the property, effectively ending any prospects for real estate development. As the dust settles, Hoops and Cassandra share a romantic kiss, marking their first tender moment together.

In the aftermath, Squid's canine companion miraculously recovers from its ordeal at the animal hospital, returning to its relieved owner with an adorable litter of new puppies in tow. The scene then shifts to George's uncle Frank, who finally secures the coveted $1 million prize in a radio call-in contest. However, just as he is about to reveal his identity and claim his reward, his phone connection drops, leaving him stunned and frustrated. In a fit of rage, Frank turns to a rocket launcher and unleashes a guided missile upon the radio station, reducing it to ashes. As the chaos unfolds, the Stork twins arrive on the scene in their trusty tow truck, where they proceed to roast marshmallows amidst the smoldering ruins.