Happy Gilmore 2: Full list of cast and characters explored
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Cast members of Happy Gilmore 2 (Image via Getty)Happy Gilmore 2, the eagerly anticipated follow-up to the popular 1996 sports comedy, is co-written by the original screenplay's authors, Adam Sandler and Tim Herlihy and directed by Kyle Newacheck. This sequel is an original story that follows Happy's adventure almost 30 years after the first one and isn't based on any previous narrative or literature. The movie premiered exclusively on Netflix on July 25, 2025 in the United States.
It begins with Happy Gilmore (Adam Sandler), who is now retired and working at a grocery store. He is dealing with bereavement, drunkenness, and poverty after his wife Virginia died tragically from a wayward golf shot—an unintentional incident that creates a depressing atmosphere. When Sandler's real-life daughter Sunny portrays his young daughter Vienna, who aspires to attend ballet school in Paris, Happy returns to competitive golf in order to finance her dreams.
The film has a runtime of 118 minutes. Both viewers and critics enjoy the movie. Happy Gilmore 2 three has a 65% "fresh" certification and a 75% audience score on the movie and television rating website Rotten Tomatoes.
Exploring the cast & crew members of Happy Gilmore 2
Adam Sandler as Happy Gilmore
Happy Gilmore 2 features Adam Sandler reprising his well-known portrayal of Happy Gilmore. After retiring as a legend, Happy is now an alcoholic single father of five who plays competitive golf again to pay for his daughter Vienna's ballet school tuition. He eventually portrays a man struggling with loss and redemption while rediscovering his long-lost comedic appeal in this nostalgic mashup of outrageous antics, emotional depth, and appearances.
An American comedian and actor Adam Sandler was born on September 9, 1966. He is known for his role in projects such as Saturday Night Live (1990-24), Dracula Raps (2022-24), and Leo (2023).
Julie Bowen as Virginia Venit Gilmore
In Happy Gilmore 2, Julie Bowen plays Virginia Venit Gilmore again, making brief flashback appearances before being killed early on by Happy's stray golf ball. Her character passes away in the first few scenes, but she is still there in Happy's dreams and emotional recollections, helping him deal with his loss and influencing his decision to resume playing competitive golf as a single father of five. Her passing establishes the tone for the whole follow-up.
American actress Julie Bowen won the Primetime Emmy Award for Outstanding Supporting Actress in a Comedy Series in 2011 and 2012. Some of her previous works are Hysteria! (2024), American Dad! (2022), and Totally Killer (2023)
Maxwell Jacob Friedman, Conor Sherry, Ethan Cutkosky, Philip Fine Schneider, and Sunny Sandler as The Gilmore Kids
Maxwell Jacob Friedman, Conor Sherry, Ethan Cutkosky, Philip Fine Schneider, and Sunny Sandler portray the Gilmore children in Happy Gilmore 2. Ethan Cutkosky plays Wayne, Maxwell Jacob Friedman is Gordie, Philip Fine Schneider appears as Bobby, and Conor Sherry takes on the role of Terry. Sunny Sandler plays Vienna, the only daughter who helps Happy return to the professional golf scene by pursuing her dream of going to ballet school. This lively sibling trio adds heart, humor, and chaos to their father's humorous yet poignant journey of loss and atonement.
Some of these young actors have previously appeared in projects such as AEW Collision (2023-25), The Terminal List (2022), The Conners (2022), FBI: Most Wanted (2021), and Leo (2023).
Christopher McDonald as Shooter McGavin
Christopher McDonald returns to his iconic role as Happy Gilmore's longtime rival, Shooter McGavin. Shooter, who was released from a mental institution 30 years after their first match, makes a comeback to the professional golf scene to take on Happy once more. He continues to act haughtily and disparagingly, calling Happy "caddie-bait" and inciting a cemetery fight that is taken directly from the original movie's script.
Christopher McDonald is an American actor. His notable works include Hacks (2025), and The Last Rodeo (2025)
Bad Bunny as Oscar Mejías
In Happy Gilmore 2, Benito Antonio Martínez Ocasio (Bad Bunny) portrays Oscar Mejías. After being sacked by his snooty waiter supervisor (played by Travis Kelce), Oscar, a well-meaning but uncomfortable former restaurant busboy, is sympathetically hired by Happy Gilmore as his golf caddy. An eager and enthusiastic Oscar adds a unique energy to the green, most notably in a humorous "happy place" vision in which he ties his former boss to a pole and covers him in honey, triggering a bear encounter as symbolic retaliation.
Bad Bunny is a Puerto Rican rapper, singer, actor, and record producer, known for his work in music video such as Bad Bunny: Nuevayol (2025), Bad Bunny: KETU TeCRÉ (2025)
Supporting cast of Happy Gilmore 2
The film features a talented ensemble of actors in supporting roles, some of whom are listed as follows:
- Benny Safdie as Frank Manatee
- Jackie Sandler as Monica
- Sadie Sandler as Charlotte
- Sunny Sandler as Vienna Gilmore
- Dennis Dugan as Doug Thompson
- Kevin Nealon as Gary Potter
- Haley Joel Osment as Billy Jenkins
- Lavell Crawford as Slim Peterson
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