Happy Gilmore cast: Where are they now from award wins to tragic loss of legends

Happy Gilmore 2 has finally arrived on Netflix, with countless comedy fans expected to tune into the long-awaited sequel this weekend.

Returning to one of his most beloved roles, Adam Sandler once again steps into the shoes of the rambunctious ex-hockey player who discovers a talent for unconventional golfing.

In the sequel, which is nearly 30 years in the making, Happy is left reeling after an unexpected tragedy and is compelled to take up golfing once again to help his daughter, Vienna (played by Sunny Sandler), pursue her dreams of being a dancer.

Featuring cameos galore and plenty of gags, the movie hasn’t received a Rotten Tomatoes rating just yet but is guaranteed to go down a treat with die-hard fans of the original.

With plenty of returning stars from the original film set to make appearances, let’s take a look at what the cast have been up to in the last 20 years.

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Adam Sandler

Iconic funnyman Adam Sandler led the original comedy and of course returns for the sequel as the washed up hockey player who becomes a golfer.

Nearly 30 years after the sequel, Sandler, 58, has become one of the most successful comic actors in Hollywood, starring in hits like The Wedding Singer, 50 First Dates, Click and Grown Ups.

He’s also branched out his career with a number of acclaimed dramatic roles, including Punch-Drunk Love, Uncut Gems and Hustle, as well as voicing Dracula in the hit Hotel Transylvania animated series.

Outside of showbiz, Sandler has been married to his wife Jaqueline ‘Jackie’ Sandler since 2003. They have two daughters, Sadie and Sunny, both of whom appeared with their dad in the coming-of-age comedy You Are So Not Invited to My Bat Mitzvah as well as Happy Gilmore 2.

Christopher McDonald

Christopher McDonald is best known to fans as Happy’s volatile rival, Shooter McGavin, who also returns for the sequel.

He’s also had roles in major films like Thelma and Louise, opposite his former fiancée Geena Davis, Leave It to Beaver, Requiem for a Dream and The House Bunny.

Away from the screen, he’s been married to actress Lupe Gidley since 1992 and have three daughters and a son together.

Julie Bowen

Julie Bowen portrayed Happy’s love interest Virginia Venit in the original film and has since become a household name for her role as Claire Dunphy in the hit ABC sitcom Modern Family.

She held the role for over a decade and was nominated six times for a Primetime Emmy Award, taking home two trophies.

Bowen is also returning for Happy Gilmore 2, and away from the screen married real estate investor and software developer Scott Phillips in 2004.

They have three sons together, though Bowen filed for divorce from Phillips citing irreconcilable differences in February 2018. It was finalised in September that year.

Frances Bay

Legendary Canadian comedian Frances Bay portrayed Happy’s grandmother in the original film after becoming a screen legend with roles in shows like Happy Days, The Dukes of Hazzard, Cheers and Seinfeld.

After the first film she went on to star in the likes of Charmed, Grey’s Anatomy and The Middle whilst also scoring roles in films like Stranger than Fiction and The Wedding Planner.

Sadly, she won’t be appearing in Happy Gilmore 2 as she passed away at the age of 92 in 2011, due to complications from pneumonia.

Allen Covert

Sandler’s frequent collaborator Allen Covert portrayed homeless man Otto in the 1996 flick, eventually becoming Happy’s caddy.

He’ll be back in the sequel after co-starring with the comedy star in films including Big Daddy, The Wedding Singer, Anger Management and 50 First Dates.

Covert has been either a supporting actor or producer for almost all of Sandler’s projects and shared he has plans to found his own production company to support the return of R-rated comedies to cinemas. He was married to Kathryn Ashley Hagstrom in 2006, though he filed for divorce in 2019.

Richard Kiel

‘Gentle Giant’ Richard Kiel was known for his incredible height of 7 feet 1.5 inches and famously portrayed the James Bond villain Jaws in The Spy Who Loved Me and Moonraker.

He also played Happy’s intimidating boss Mr Larson in the original film, though unfortunately won’t return in the sequel. Kiel passed away from heart disease on 10th September, 2014, three days before his 75th birthday.

Kiel was previously married to Faye Daniels from 1960-1973. He then married Diane Rogers a year later and they remained together until his death, welcoming four children and nine grandchildren over their 40-year marriage.

Ben Stiller

A-list comedy actor took on an uncredited role as the abusive orderly Hal who torments Happy’s grandma in the original movie.

He’s since become globally recognised for his roles in Zoolander, Tropic Thunder, Meet the Parents and the Night at the Museum franchise, as well as more dramatic parts in While We're Young, The Meyerowitz Stories and Brad's Status.

Stiller has also directed several of his most iconic films, including Zoolander, Tropic Thunder and The Secret Life of Walter Mitty. He has since received acclaim for director episodes of the hit Apple TV+ sci-fi drama Severance.

Away from his career, Stiller has been married to actress Christine Taylor since 2000, going on to star together in several films. They temporarily separated in 2017, but reconciled when they lived together during the Covid-19 pandemic. They have a daughter, Ella, and a son, Quinn.

Carl Weathers

One of the most fondly remembered parts of the original Happy Gilmore is Carl Weathers as Happy’s coach, Chubb Peterson, who famously had his hand bitten off by an alligator.

He was also remembered for portraying a fictionalised version of himself in Arrested Development, though before turning to comedy was known for his iconic portrayal of Apollo Creed in the Rocky franchise, as well as Colonel Al Dillon in the original Predator film with Arnold Schwarzenegger.

In recent years Weathers returned to the mainstream by playing Greef Karga in the Star Wars spin-off series The Mandalorian, picking up an Emmy nomination for his performance.

Happy Gilmore 2 frequently plays tribute to the star, as Weathers sadly died last year at the age of 76 from a suspected atherosclerotic cardiovascular disease.

He married three times though was survived by his partner of 10 years Christine Kludjian.

Happy Gilmore is available to stream on Netflix.