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Home»Entertainment

Happy Gilmore cast then and now – from award wins to devastating loss of legends

amedpostBy amedpostJuly 25, 2025 Entertainment No Comments6 Mins Read
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Happy Gilmore 2 has finally landed on Netflix, with numerous comedy enthusiasts expected to watch the eagerly anticipated sequel this weekend.

Adam Sandler returns to one of his most cherished roles, once again portraying the boisterous ex-hockey player who uncovers a knack for unconventional golfing.

In the sequel, which has been almost 30 years in the making, Happy is left stunned after an unforeseen tragedy and feels obliged to return to golf to support his daughter, Vienna (portrayed by Sunny Sandler), in her aspirations to become a dancer.

With a host of cameos and a plethora of jokes, the film hasn’t yet received a Rotten Tomatoes rating but is sure to be a hit with devoted fans of the original.

With many stars from the original film set to make appearances, let’s see what the cast have been doing over the past two decades, reports the Mirror.

Adam Sandler

Adam Sandler finally returns to one of his most iconic roles (Image: UNIVERSAL/GETTY)

Read more: Happy Gilmore 2 review – obnoxious Netflix sequel is more cameos than comedy

Read more: Pamela Anderson series she demanded a ‘public apology’ for is free to watch

Adam Sandler

Legendary comedian Adam Sandler led the original comedy and naturally returns for the sequel as the down-and-out hockey player turned golfer.

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

He’s also diversified his career with several acclaimed dramatic roles, including Punch-Drunk Love, Uncut Gems and Hustle, as well as providing the voice for Dracula in the popular Hotel Transylvania animated series.

Away from the glitz and glamour of Hollywood, Sandler has been happily married to his wife Jaqueline ‘Jackie’ Sandler since 2003. The couple have two daughters, Sadie and Sunny, who have both made appearances alongside their father 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 portrays Happy’s unpredictable rival, Shooter McGavin (Image: UNIVERSAL/GETTY)

Christopher McDonald

Best known for his role as Happy’s fiery rival, Shooter McGavin, Christopher McDonald is set to return for the sequel. He’s also had significant roles in major films such as Thelma and Louise, where he starred opposite his former fiancée Geena Davis, Leave It to Beaver, Requiem for a Dream and The House Bunny.

Off-screen, he’s been happily married to actress Lupe Gidley since 1992, and they have three daughters and a son together.

Julie Bowen

Julie Bowen went on to win two Emmy Awards for Modern Family (Image: UNIVERSAL/GETTY)

Julie Bowen

Julie Bowen, who played Happy’s love interest Virginia Venit in the original film, has since become a household name due to her role as Claire Dunphy in the hit ABC sitcom Modern Family.

She held this role for over a decade, earning six Primetime Emmy Award nominations and winning two trophies.

Bowen is also set to return for Happy Gilmore 2. Away from the screen, she married real estate investor and software developer Scott Phillips in 2004.

The couple have three sons together, but Bowen filed for divorce from Phillips citing irreconcilable differences in February 2018. The divorce was finalised in September that year.

Frances Bay

Legendary actress Frances Bay sadly died in 2011 aged 92 (Image: UNIVERSAL/GETTY)

Frances Bay

Frances Bay, the legendary Canadian comedian, won’t be gracing the screen in Happy Gilmore 2.

Best known for her role as Happy’s grandmother in the original film and her appearances in popular shows like Happy Days, The Dukes of Hazzard, Cheers and Seinfeld, she sadly passed away at the age of 92 in 2011 due to complications from pneumonia.

Allen Covert

Allen Covert has worked on nearly every Adam Sandler project (Image: UNIVERSAL/GETTY)

Allen Covert

Allen Covert, a frequent collaborator with Sandler, will be reprising his role as Otto, the homeless man turned caddy from the 1996 film.

Having co-starred with Sandler in films such as 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.

He revealed plans to establish his own production company to bring back R-rated comedies to cinemas. He married Kathryn Ashley Hagstrom in 2006, but filed for divorce in 2019.

Richard Kiel

‘Gentle Giant’ Richard Kiel passed away in 2014 (Image: UNIVERSAL/GETTY)

Richard Kiel

Richard Kiel, known as the ‘Gentle Giant’ due to his towering height of 7 feet 1.5 inches, is famous for his role as the James Bond villain Jaws in The Spy Who Loved Me and Moonraker.

Regrettably, Kiel, who played the role of Happy’s formidable boss Mr Larson in the original film, will not be returning for the sequel. He passed away from heart disease on 10th September, 2014, just three days shy of his 75th birthday.

Kiel was first married to Faye Daniels from 1960-1973 before tying the knot with Diane Rogers a year later. The couple remained together until his death, raising four children and nine grandchildren during their 40-year marriage.

Ben Stiller

Ben Stiller returns as Hal the abusive orderly (Image: UNIVERSAL/NETFLIX)

Ben Stiller

The A-list comedy actor had an uncredited role as the abusive orderly Hal, who torments Happy’s grandma in the original film.

Stiller has since gained international recognition for his roles in films such as Zoolander, Tropic Thunder, Meet the Parents and the Night at the Museum franchise, as well as more serious parts in While We’re Young, The Meyerowitz Stories and Brad’s Status.

In addition to acting, Stiller has directed several of his most iconic films, including Zoolander, Tropic Thunder and The Secret Life of Walter Mitty. His directorial skills have been praised in recent times for directing episodes of the hit Apple TV+ sci-fi drama Severance.

Away from his professional life, Stiller has been married to actress Christine Taylor since 2000, with the pair starring together in several films. They briefly separated in 2017, but reconciled when they lived together during the Covid-19 pandemic.

They are parents to a daughter, Ella, and a son, Quinn.

Carl Weathers

Iconic star Carl Weathers passed last year after huge roles in Rocky, Predator and Star Wars (Image: UNIVERSAL/GETTY)

Carl Weathers

Carl Weathers, who played the role of Happy’s coach, Chubb Peterson, in the original Happy Gilmore, is hilariously remembered for his character losing a hand to an alligator.

He also made a mark with his portrayal of a fictionalised version of himself in Arrested Development, but before turning to comedy, he was known for his iconic roles as Apollo Creed in the Rocky franchise and Colonel Al Dillon in the original Predator film alongside Arnold Schwarzenegger.

In recent years, Weathers returned to mainstream media with his role as Greef Karga in the Star Wars spin-off series The Mandalorian, earning him an Emmy nomination.

Sadly, Weathers passed away last year at the age of 76 due to suspected atherosclerotic cardiovascular disease, and Happy Gilmore 2 pays frequent tributes to the star.

Despite being married three times, he is survived by his partner of 10 years, Christine Kludjian.

Happy Gilmore is available to stream on Netflix.

adam sandler award cast Cast Updates comedy devastating Gilmore happy happy gilmore 2 happy gilmore 2 cast happy gilmore cast now happy gilmore cast then and now happy gilmore original cast Hollywood james bond legends loss Netflix Star Wars wins

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