The Cast of ‘Happy Gilmore 2’ Is Packed With Surprises – Including Adam Sandler’s Wife and Two Daughters

The wait is over, and ‘Happy Gilmore 2’ has landed on Netflix, nearly three decades after the original ‘Happy Gilmore’ became a comedy classic. Adam Sandler is back as the wild-swinging golfer Happy Gilmore, delivering the same chaotic energy that made the first film a fan favorite, but with a new emotional depth that ties the story to his family.

This sequel surprises with a packed cast that blends returning stars, new talent, and a slew of cameos from sports icons and celebrities. What makes it extra special is the involvement of Sandler’s own daughters and wife, adding a personal touch to the golf course shenanigans. Let’s break down the key players who make this film a hole-in-one.

Adam Sandler as Happy Gilmore

Adam Sandler returns as Happy Gilmore, the former hockey player with a monstrous golf swing and a short fuse. In ‘Happy Gilmore 2’, Happy’s life has taken a dark turn—he’s quit golf, fallen into alcoholism, and lost nearly everything after a tragic accident.

The story follows his comeback to raise money for his daughter’s ballet school dreams. Sandler’s performance mixes his classic humor with a more grounded, emotional side, making Happy’s journey both hilarious and heartfelt.

Sunny Sandler as Vienna Gilmore

Sunny Sandler, Adam’s 16-year-old daughter, plays Vienna, Happy’s daughter and the heart of the sequel’s plot. Her dream to attend a top ballet school in Paris pushes Happy to dust off his clubs and get back on the course.

Sunny shines in her role, bringing a natural warmth and chemistry with her real-life dad. Her performance shows she’s ready to step out of her father’s shadow and make her mark.

Sadie Sandler as Charlotte

Sadie Sandler, Adam’s 19-year-old daughter, takes on the role of Charlotte, a member of Happy’s support group who later reveals a surprising twist as an undercover FBI agent. Her character adds both humor and intrigue to the story.

Currently studying acting at NYU’s Tisch School of the Arts, Sadie delivers a confident performance that holds its own among the star-studded cast. Her scenes with Adam feel authentic, showcasing their real-life bond.

Jackie Sandler as Monica

Jackie Sandler, Adam’s wife, appears as Monica, Vienna’s ballet instructor, in a brief but meaningful cameo. She sets the story in motion by urging Happy to help fund Vienna’s dreams, adding a spark to the plot.

Jackie’s warm presence is a familiar treat for fans of Sandler’s films, and her role here feels like a loving nod to their long partnership. It’s short but sweet, tying the family dynamic together.

Julie Bowen as Virginia Venit

Julie Bowen reprises her role as Virginia Venit, Happy’s late wife, who appears in flashbacks and as a ghostly figure offering guidance. Her limited screen time still captures the charm and heart she brought to the original.

Bowen has praised the family-friendly vibe on set, especially Adam’s support for his daughters. Her return adds a nostalgic touch, reminding me why Virginia was such a key part of Happy’s story.

Christopher McDonald as Shooter McGavin

Christopher McDonald is back as Shooter McGavin, Happy’s arrogant rival who’s now a washed-up has-been plotting his comeback. His over-the-top villainy remains a highlight, delivering laughs with every sneer.

McDonald’s chemistry with Sandler reignites their iconic feud, and his commitment to the role makes Shooter as hateable as ever. It’s a joy to see him chew the scenery in true ‘90s fashion.

Ben Stiller as Hal L.

Ben Stiller returns as Hal L., the unhinged orderly from the first film, now leading a support group that Happy attends. His wild energy and bizarre one-liners steal every scene he’s in.

Stiller’s cameo is a fan-favorite nod to the original, and his ability to go full chaotic makes Hal a standout. It’s a small role, but he makes it unforgettable with his signature intensity.

Bad Bunny as Oscar Mejias

Bad Bunny, credited as Benito Antonio Martínez Ocasio, plays Oscar Mejias, Happy’s clueless but lovable caddy. His comedic timing and charm bring a fresh vibe to the film.

As a global music star, Bad Bunny surprises with his natural humor, making Oscar a fan favorite. His scenes with Sandler are packed with laughs, proving he’s got acting chops to match his music.

Benny Safdie as Frank Manatee

Benny Safdie joins the cast as Frank Manatee, the shady CEO of Maxi Energy Drink, who’s pushing an extreme version of golf that Happy must confront. His slick, villainous role adds a new layer to the story.

Known for directing films like ‘Uncut Gems’ (2019), Safdie shows his acting range here. His character’s schemes keep the stakes high, making him a perfect foil for Happy’s chaos.

Travis Kelce as Hotel Employee

NFL star Travis Kelce pops up as a hotel employee in a brief but memorable cameo. His natural charisma and quick wit make his small role a standout moment.

Kelce’s appearance, alongside other sports figures, adds a fun real-world touch to the film. He’s clearly having a blast, and it’s easy to see why the set felt electric with him around.

Dennis Dugan as Doug Thompson

Dennis Dugan, who directed the original ‘Happy Gilmore’, returns as Doug Thompson, the golf tour commissioner. His character navigates the chaos of Happy’s return and Shooter’s schemes.

Dugan’s familiar face is a treat for longtime fans, and his dry humor fits perfectly in the golf world. It’s a nice touch to see him back in front of the camera.

Kevin Nealon as Gary Potter

Kevin Nealon reprises his role as Gary Potter, the quirky golfer turned sports commentator. His zen-like musings and deadpan delivery bring a calm contrast to Happy’s wild energy.

Nealon’s return feels like catching up with an old friend. His scenes are packed with subtle humor, making Gary a quiet but essential part of the sequel’s charm.

Haley Joel Osment as Billy Jenkins

Haley Joel Osment plays Billy Jenkins, a young golfer with a swing that rivals Happy’s. His character’s arc, defecting to the rival Maxi Golf team, adds tension to the plot.

Osment, known for ‘The Sixth Sense’ (1999), brings a mix of intensity and humor to the role. His performance feels fresh, making Billy a worthy addition to the golfing chaos.

Lavell Crawford as Slim Peterson

Lavell Crawford plays Slim Peterson, the son of Chubbs Peterson, Happy’s late mentor from the original. Like his father, Slim has a prosthetic hand and a big personality.

Crawford’s comedic chops shine, delivering laughs while honoring Chubbs’ legacy. His scenes with Happy are heartfelt, adding depth to the film’s nostalgic tributes.

Kym Whitley as Bessie

Kym Whitley plays Bessie, a lively member of Happy’s support group who brings humor and heart to the story. Her scenes are packed with energy, making her a standout in the ensemble.

Whitley’s warmth and comedic timing make Bessie a memorable addition. She’s described working with Sandler as a joy, and it shows in her vibrant performance.

Cameos Galore

The film is bursting with cameos that keep things exciting. Golf stars like Rory McIlroy, Paige Spiranac, John Daly, Bryson DeChambeau, and Scottie Scheffler appear as themselves, adding authenticity to the golf scenes.

Celebrities like Eminem as a heckling golfer, Post Malone, Cam’ron, and Ken Jennings in quick roles bring extra star power. These surprise appearances make every scene a potential Easter egg for fans.

Which cameo in ‘Happy Gilmore 2’ stole the show for you, or did I miss a favorite? Share your thoughts in the comments!