Happy Gilmore Stars, Then and Now: See How the Cast Has Changed Since the Film’s 1996 Premiere

Adam Sandler in ‘Happy Gilmore’ and ‘Happy Gilmore 2.’. Credit :

Moviestore/Shutterstock; Netflix

  • Happy Gilmore premiered in 1996 and starred Adam Sandler, Julie Bowen, Christopher McDonald and more
  • Happy Gilmore 2 debuted on Netflix on July 25
  • The sequel adds new faces, including Travis Kelce, Bad Bunny and Eminem

Adam Sandler’s classic sports comedy Happy Gilmore is back for more laughs.

The 1996 movie follows Sandler’s Happy Gilmore, a failed hockey player who uses his stick skills and anger management issues to excel in golf, all while trying to earn money to save his grandmother’s home. Sandler reprised his role for the 2025 sequel Happy Gilmore 2, which premiered on Netflix on July 25.

The sequel features new faces like Travis Kelce, Bad Bunny and Eminem alongside returning cast members like Julie Bowen and Christopher McDonald.

In July 2025, McDonald assured fans that the sequel still incorporates Sandler’s signature hallmarks.

“[Happy Gilmore 2 is] about family and friends and love and basically a lot of heart, which I love about Adam Sandler’s movies,” McDonald told PEOPLE. “What I love about Adam Sandler is his heart. He’s got so much love for people.”

So, what have the stars of Happy Gilmore been up to in the nearly three decades since the film premiered? Here’s everything to know about where the cast members are now.

Adam Sandler in 1996; Adam Sandler in 2024. Universal/Getty; Dominique Charriau/WireImage

Sandler’s portrayal of Happy Gilmore has become one of his most famous for his over-the-top comedic anger, which turns more heartfelt as the film progresses.

After Happy Gilmore, Sandler continued showcasing his comedic chops for decades with films like Big Daddy, Mr. Deeds, 50 First Dates, Grown Ups and Hubie Halloween, as well as his dramatic abilities in films like Punch-Drunk Love, Uncut Gems and Hustle.

Aside from filming Happy Gilmore 2, Sandler recently starred alongside his daughters, Sadie and Sunny, in You Are So Not Invited to My Bat Mitzvah. He’s been married to his wife, Jackie Sandler, since 2003.

In August 2024, Sandler told PEOPLE that the sequel was the most excited he’d been to make a film in years.

“Well, we worked hard trying to write something that we thought people would have a good time with, and I’m more than excited, probably the most excited I’ve been in many years to shoot something,” Sandler said.

Following Happy Gilmore 2, Sandler is set to star in the coming-of-age dramatic comedy Jay Kelly alongside George Clooney.

Julie Bowen in 1996; Julie Bowen in 2025. Universal Pictures; Jamie McCarthy/Getty

Bowen plays the diligent pro golf tour director of public relations and Happy’s kind, caring love interest Virginia Venit.

Bowen rose to prominence for roles in shows like ER and Boston Legal before securing the role that she is best-known for: Modern Family‘s micro-managing mother-of-three Claire Dunphy. Bowen won two Emmys for her performance.

Since Modern Family, Bowen played yet another Sandler love interest in 2020’s Hubie Halloween. She delved into horror-comedy in 2023’s Totally Killer and the 2024 show Hysteria!.

Off-screen, Bowen filed for divorce in February 2018 from ex-husband Scott Phillips. The former couple share three children: son Oliver and twins Gustav and John.

In October 2024, Bowen told PEOPLE that she’s thrilled to be part of the sequel, although she hasn’t seen the original film since its premiere.

“I’ve seen chunks of it here and there,” Bowen said. “The Bob Barker sequence will pop up on some feed for some reason. I’m like, ‘God that was good.’ That one always makes me laugh. And anything with Carl Weathers was hilarious.”

Christopher McDonald in 1996; Christopher McDonald in 2025. Universal Pictures; Jeff Kravitz/FilmMagic

McDonald played Happy’s boastful, antagonistic golfing rival Shooter McGavin, who tried to sabotage him at every point.

Prior to Happy Gilmore, McDonald rose to prominence as Thelma’s disrespectful husband Darryl in 1991’s Thelma & Louise. McDonald continued acting throughout the years in a range of roles from films like Flubber and House Bunny to shows like Boardwalk Empire and Impeachment: American Crime Story.

These days, McDonald stars as Palmetto Casinos CEO Marty Ghilain in HBO Max’s Hacks. In 2022, McDonald received an Emmy nomination for his performance.

McDonald married Lupe McDonald in 1992. Together, they share three daughters and a son.

In May 2025, McDonald told PEOPLE that he was “over the moon” to be asked back for Happy Gilmore 2.

“I’ve been an ambassador for this movie for so long,” he said. “29 years later … They’ve outdone themselves.”

Ben Stiller in 1996; Ben Stiller in 2025. Universal Pictures; Frazer Harrison/Getty

Ben Stiller is in an uncredited role as Hal L. — a two-faced nursing home orderly who abuses Happy’s grandmother and the other tenants.

Outside of Happy Gilmore, Stiller has joined Sandler as an all-time great comedic actor with roles in comedies like There’s Something About Mary, Zoolander, Tropic Thunder and Dodgeball, as well as in franchises like Madagascar, Night at the Museum and Meet the Parents. In addition to both Happy Gilmore films, Stiller is also currently directing and executive producing Apple TV+’s Severance.

The actor has been married to Christine Taylor since 2000. They share two kids: daughter Ella and son Quinlin.

In November 2024, Stiller said he was “always ready” to reprise his role as Hal L.

“I’m always ready to play Hal L. You don’t get the opportunity to play Hal L. that often,” Stiller told Collider. “So, Hal L. — I’m saying this now in retrospect because I just did it — was so much fun. As we were doing, and I was there with Adam, I was flashing back to whatever it was, however many years ago, and just being so grateful that we’re both still here and able to connect.”

In 2026, he is set to reprise his role as Greg Focker in Meet the Parents 4 alongside Robert De Niro and Ariana Grande.

Kevin Nealon in 1996; Kevin Nealon in 2025. Universal Pictures; Dia Dipasupil/Getty

Kevin Nealon plays Happy’s overly positive AT&T Open partner Gary Potter, who comes off as more of an eccentric self-help guru impersonator than a pro golfer.

Prior to his role in Happy Gilmore, Nealon made his name in comedy with a nine-year stint on Saturday Night Live from 1986 to 1995, including as a Weekend Update host. He has appeared alongside Sandler in many Happy Madison films including The Wedding Singer, Little Nicky and Anger Management.

Nealon married actress Susan Yeagley in 2005. They welcomed a son, Gable Ness Nealon, in 2007.

Despite his career success, Nealon’s Happy Gilmore role has stuck with the actor — partially because fans quote it to him regularly.

“You know, I’ve done so many different things that are catchy,” Nealon told The Tampa Bay Times in May 2012. “It’s Happy Gilmore when I’m golfing in a pro-am tournament, people yelling out, ‘Feel the flow!’ ‘Be the ball,’ ‘Harness the good, block the bad.’ ”

Allen Covert in 1996; Allen Covert in 2022. Universal Pictures; Steve Granitz/FilmMagic

Allen Covert plays a homeless man named Otto whom Happy recruits to be his caddy.

Covert is best known for his leading role in the 2006 Happy Madison comedy Grandma’s Boy and for roles in many Sandler films, including The Wedding Singer, Little Nicky and 50 First Dates. Covert has continued working with Sandler’s production house Happy Madison throughout his career, producing or guest starring in more recent Sandler films like Leo and Murder Mystery 2.

Covert married Kathryn Covert in 2006. She filed for divorce in July 2019, per The Blast; it was finalized later that year in November, he shared in a since-deleted post on X.

In May 2020, Covert revealed why he likes working on movies produced by Happy Madison.

“Every one of them, I’ve been able to have fun and do different stuff,” Covert told Kendall Talks TV.

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