Happy Gilmore (/actor/adam-sandler) begins his story by recounting his unlikely journey from a chaotic amateur hockey player to a renowned professional golfer. His early life was marked by his fiery attitude and aggressive nature, which often led to trouble. Despite these setbacks, Happy eventually manages to make a name for himself on the golf course, where he gains fame and fortune. He is happily married to Virginia Venit (/actor/julie-bowen), with whom he has five children: Gordy, Wayne, Bobby, Terry, and Vienna (/actor/sunny-sandler). For a time, their life seems perfect, filled with success and happiness.
However, tragedy strikes during a 2014 golf tournament when Happy accidentally hits Virginia with a golf ball, leading to her death. Consumed with guilt and grief, Happy spirals into alcoholism and despair. His life takes a further downturn as he loses his grandmother and her house after going broke, forcing him to become a single father living modestly near John Daly, who is depicted here as a vagrant. Happy now works at a grocery store, constantly trying to find ways to fill the void left by his loss. He frequently uses any object he finds as a makeshift flask, reflecting his struggles with addiction.
The story takes a turn when Happy is approached by Frank Manatee (/actor/benny-safdie), a slick CEO of Maxi Energy Drink who is promoting a new golf league called Maxi Golf. Frank considers the sport outdated and wants Happy to lend it a fresh, rebellious edge. In a moment of defiance, Happy discreetly dumps Frank into a lobster tank after Frank makes a disrespectful comment about Virginia. Meanwhile, his daughter Vienna develops a passion for dancing, and her teacher Monica advises her to attend a dance school in Paris, which costs $75,000 annually. Happy’s children look after themselves financially through various part-time jobs, highlighting the economic pressures the family faces.
Vienna’s emotional burden weighs heavily on her, and she encourages her father to pursue happiness again. In his dreams, Happy visualizes Virginia, who continues to motivate him with her encouragement from beyond, even though he blames himself for her death. With a desire to rebuild his life, Happy decides to return to golf to raise money for Vienna’s dance education. His first attempts are humorous and clumsy, playing with local amateurs like Sally (/actor/margaret-qualley), Steiner (/actor/eric-andr), and Fitzy (/actor/martin-herlihy). Despite initial poor performance, a nostalgic reminder from his mentor, Chubbs (/actor/lee-trevino), about the importance of “hips” spurs him to improve his swing. His comeback seems promising, but his drunken antics, including riding golf carts recklessly and crashing into others, land him in jail and cause further trouble.
At a mental hospital, Happy’s old adversary, Shooter McGavin (/actor/christopher-mcdonald), is being held for parole. Shooter’s attempt at freedom is thwarted when he is angered by Happy’s presence, highlighting their long-standing rivalry. Happy’s path to redemption faces additional hurdles when he’s ordered into a radical alcohol treatment program, run by none other than Ben Stiller, who portrays a sinister orderly abusing patients and exploiting the facility. During this time, Happy befriends Charlotte (/actor/sadie-sandler), a teenager, as he tries to stay sober and focus on training for a comeback in golf.
As Happy works tirelessly to regain his skills, he attends a prestigious golf event hosted by Doug Thompson (/actor/dennis-dugan). He suggests a match between Maxi Golf and traditional golf, sparking a rivalry that culminates in a major tournament. Happy befriends a busboy named Oscar (/actor/bad-bunny), whom he takes as his caddie after witnessing the bullying Oscar endures from a fellow waiter (/actor/travis-kelce). During the competition, Happy faces off against Will Zalatoris, the caddie he once choked during his early days. Using his mental tricks, such as revisiting his “happy place,” Happy manages to beat Zalatoris, who retaliates by choking his own caddie, adding comic drama to the match.
Frank’s greed and ambition lead him to reintroduce Shooter into Maxi Golf, seeking to gain an edge with the help of illegal procedures that enhance hip flexibility—akin to the infamous case of golfer Ben Daggett (/actor/nick-swardson). Shooter, disgusted by the unethical practices, has a confrontation with Frank after learning about the operation plans, resulting in Shooter fleeing in outrage. Happy, now aware of the scheme, teams up with his old rival to stop Maxi Golf from cheating. They reunite with Slim Peterson (/actor/lavell-crawford), the son of Chubbs, who despite his own injuries, agrees to join forces, along with other professional golfers.
The climax centers on a high-stakes, elaborate golf course competition featuring a team of Maxi Golf players—Billy Jenkins (/actor/haley-joel-osment), Harley (/actor/oliver-hudson), and others. Frank’s manipulations include using a platform to hinder shots, fueling tension and chaos. Despite setbacks like injuries and interference, Happy taps into his newfound inner strength and rage, ultimately outplaying Maxi Golf with the help of Oscar and his team. The final moments see Happy winning the tournament after a tense drill involving a last shot on the final hole. His victory symbolizes his return to sobriety and happiness.
In a heartfelt closing scene, Happy celebrates his sobriety and personal growth. When a colleague dismisses his achievements, Charlotte reveals that she betrayed Hal Stiller (/actor/ben-stiller), the abusive orderly, leading to his disgrace. Happy visits Virginia’s grave, and with his opponents watching, he prepares to participate in the British Open, promising a new chapter in his life. As his spirit is uplifted by visions of friends like Chubbs (/actor/lee-trevino) and Virginia, Happy walks home after realizing that while life still holds challenges, he's back on his path to happiness—despite the small inconvenience of an uncharged electric car.
During the credits, it’s revealed that Frank’s Maxi Energy Drink was shut down for causing health issues like gingivitis and bad breath, leading Frank to go into hiding. Meanwhile, some golf pros, such as Scottie Scheffler (/actor/scottie-scheffler), continue their careers, while others, like Scheffler, opt to stay in prison a bit longer, humorously enjoying chicken tenders behind bars.