Love him or hate him, there’s something about Adam Sandler that keeps audiences coming back to his movies. His latest, The Ridiculous 6, became the most viewed movie on Netflix and his films have grossed a total of $4.8 billion worldwide. But back in 1996, he was just coming off Billy Madison and beginning to establish himself as a legitimate star outside of Saturday Night Live.

Happy Gilmore, the sports comedy about a wannabe hockey player with a bad temper who uses his innate talent for golf to save his grandmother’s house, earned the ire of critics when it was initially released. It also made nearly $40 million at the box office on a budget of $12 million. With the help of TV personality Bob Barker, the film has since become a cult favorite and remains one of Sandler’s most beloved.

With its 20th anniversary quickly approaching, it’s time to take a look at where the stars have landed since the comedy’s release on Feb. 16, 1996.

12. Bob Barker – Himself

bob barker happy gilmore1 The Cast of Happy Gilmore: Where Are They Now?


He’s only in the film for a few minutes, but Bob Barker participates in one of the most memorable and unexpected moments. After being paired with a newly zen Gilmore, things quickly escalate when an unruly fan pops up. Gilmore becomes agitated with the heckler and takes it out on Barker via a punch to the face. A surprisingly agile Barker fights back and the two then engage in a comedic fight scene that has become synonymous with the film.

The white-haired and heavily tanned television personality hosted the hit game show The Price Is Right for 35 years until retiring in 2007. He’s made sporadic appearances on shows like The Nanny and How I Met Your Mother, and even hosted an episode of WWE Raw in 2009. He also voiced Bob Barnacle, a snail business owner, on Nickelodeon’s SpongeBob Squarepants. He made headlines in October after taking a nasty fall and hitting his head, but reports say his injuries were minor. The ex-TV cost recently appeared on Best Time Ever with Neil Patrick Harris but is otherwise enjoying his retirement at 92 years young.

11. Will Sasso – Mover

will sasso happy gilmore1 The Cast of Happy Gilmore: Where Are They Now?


In an unnamed role, Sassy played one of the movers who challenges Happy Gilmore to hit a golf ball further than he can. This inspires Gilmore to hustle more golfers with his hidden talent for swinging a golf club, so you could say the movers play an integral part in the movie.

Despite a bit part in the movie, Sasso went on to find major success in comedy. In 1997, he join the cast of MADtv and became a fan favorite for his impersonations of Kenny Rogers and Bill Clinton. He’s also had the good fortune of joining a few television shows for at least a season, including the sci-fi series Sliders and the sitcom $#*! My Dad Says. He also appeared in Family Guy, Children’s Hospital and The Cleveland Show. He currently has four projects either announced, filming or in post-production.

10. Joe Flaherty – Donald the Unruly Fan

joe flaherty happy gilmore The Cast of Happy Gilmore: Where Are They Now?


When Gilmore finally learned to control his temper, Shooter McGavin (Christopher McDonald) saw fit to destroy that progress by hiring a heckler to set him off. Donald, the unruly fan, followed Gilmore closely and found ways to berate him at the most inopportune moments. He accomplished his goal and helped start the fire that would soon turn into a major brawl with television personality Bob Barker.

By the time Happy Gilmore came around, Flaherty had appeared in a number of movies, including Back to the Future Part II. The comedian came up through the Second City Network, which is a breeding ground for future Saturday Night Live cast members like Gilda Radner, Dan Aykroyd, Chris Farley, Tina Fey, Amy Poehler, Cecily Strong and Aidy Bryant. He didn’t quite reach leading man status, but he has found steady work with appearances in shows like Family Guy, parodying the role he played in Back to the Future. He also starred in the dramedy Freaks and Geeks as Harold Weir, the father of two teens and recently had a role on the short-lived Canadian series Call Me Fitz.

9. Dennis Dugan – Doug Thompson

dennis dugan happy gilmore1 The Cast of Happy Gilmore: Where Are They Now?


As the commissioner of the Pro Golf Tour, Thompson wasn’t too happy with Gilmore’s violent outbursts, and contemplated removing him from the tour. However, Virginia Venit (Julie Bowen) changes his mind, but the commissioner does put her job on the line should Gilmore fail to play nice.

Adam Sandler loves to work with his friends, and Dennis Dugan is a frequent collaborator. The actor and director also appeared in Big Daddy, I Now Pronounced You Chuck and Larry, You Don’t Mess with the Zohan, That’s My Boy and Grown Ups 2. He also directed most of those movies. Aside from Happy Madison productions, Dugan directed the 1990s film Problem Child, six episodes of NYPD Blue and other shows. He will soon add writer to his resume with The Queen’s Corgis: Dognapped, which he will also direct.

8. Richard Kiel – Mr. Larson

richard kiel happy gilmore1 The Cast of Happy Gilmore: Where Are They Now?


Mr. Larson was Gilmore’s former boss and a pain in Shooter McGavin’s (Christopher McDonald) side. His brief but memorable role found him commenting on the sidelines and insulting or threatening McGavin, much to the golf villain’s dismay.

In real life, was a legendary actor who starred as Jaws in the James Bond films and appeared on popular shows like Gilligan’s Island, I Dream of Jeannie and The Incredible Hulk. His career had slowed down by the time Happy Gilmore came out, but he did end up voicing Vlad in Disney’s Tangled. After decades in film and television, the 7’2’’ actor died in 2014 at the age of 72.

7. Kevin Nealon – Gary Potter

kevin nealon happy gilmore The Cast of Happy Gilmore: Where Are They Now?


Potter was Gilmore’s first opponent on the Pro Golf Tour who appears to be very nice but also slightly off his rocker. When Gilmore confides in him about the presence of the media, Potter advises him to “harness in the good energy” and “block out the bad.” It seems like sound advice, were it to come from anyone but the eccentric golfer.

Like others in the cast, Nealon knew Adam Sandler before the movie’s released. The previously worked together on Saturday Night Live and Nealon would go on to appear in more of his movies. Additional Sandler production appearances include Little Nicky, Joe Dirt and Eight Crazy Nights. The comedian found his niche in productions outside of Happy Madison with TV shows like Still Standing, ‘Til Death, Glenn Martin DDS and Weeds.

6. Allen Covert – Otto

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Otto was the heavily-bearded homeless man Gilmore brings on the Pro Golf Tour to be his caddy. While his role in the film is quite small, he leaves a memorable mark thanks to the beer hat he wears and sips on while watching his new friend golf.

Covert knew Sandler before this film and went on to frequently collaborate with the comedian in even more films. Additional Sandler productions he appeared in include The Wedding Singer, The Waterboy, Big Daddy, Little Nicky, Mr. Deeds, Grown Ups 2 and Hotel Transylvania.

5. Carl Weathers – Chubbs Peterson

carl weathers happy gilmore The Cast of Happy Gilmore: Where Are They Now?


As a former golf star and current club pro, Chubbs was the mentor Gilmore needed to break into the golf world. They meet at the driving range when the short-tempered hockey hopeful was looking to hustle some golfers for extra money. Chubbs convinces him to participate in the local tournament but is dismayed he ends up joining the Pro Golf Tour. Against his advice to wait at least six months, Gilmore encounters a few stumbles along the way. After seeing him progress, Chubbs offers him a modified putter that looks like a hockey stick. Gilmore returns the favor with the head of the alligator that bit his hand off. Startled, Chubbs dies after falling through the window, although his ghost does pop up in the end to congratulate Gilmore on his big win.

Weathers’ role in the film helped change the way the industry saw him. Before this, he predominantly starred in action roles such as Apollo Creed in the Rocky saga and the titular character in Action Jackson. After the movie came out, he reprised his role in Little Nicky and even played a fictionalized version of himself in Arrested Development.

4. Frances Bay – Grandma Gilmore

frances bay happy gilmore The Cast of Happy Gilmore: Where Are They Now?


Gilmore’s sweet grandmother faced serious financial trouble that left her in a nursing home under the watch of a sadistic manager named Hal (Ben Stiller). Luckily, her faithful grandson gets her out of that awful situation and we rarely see her for the rest of the movie. We know it all works out for her in the end because Gilmore wins back her house and probably made enough money to keep her comfortable for the rest of her life. Cheers for that.

Bay didn’t start acting until she reached middle age, but found steady roles as a character actress since 1977. After Happy Gilmore, she continued on with roles in shows in Seinfeld, Charmed and Hannah Montana, and in films like The Wedding Planner and Inspector Gadget. Her last major TV role was in the sitcom The Middle as Aunt Ginny. She died in 2011 at the ripe old age of 92.

3. Julie Bowen – Virginia Venit

julie bowen happy gilmore1 The Cast of Happy Gilmore: Where Are They Now?


Virginia was the beautiful public relations director who always seemed to be on Gilmore’s side. After his explosive outburst, Commissioner Doug Thompson (Dennis Dugan) contemplated removing him from the tour but she changed his mind. She even volunteers to work with him on his anger issues, which actually works—until he encounters Bob Barker. Missteps aside, her faith in him paid off because he ended up defeating McGavin in one final match.

The movie didn’t exactly launch Bowen’s career. She had already appeared in a few movies and starred in a TV show called Extreme the year before that. Years after the film, however, she began to really carve a place in television with roles in shows like ER, Ed with Tom Cavanagh, Lost, Weeds and Boston Legal. It wasn’t until her breakout role as Claire Dunphy on Modern Family that she saw major critical success. The part earned her six consecutive Primetime Emmy Award nominations for Outstanding Supporting Actress in a Comedy. She took home the trophy in 2011 and 2012.

2. Christopher McDonald – Shooter McGavin

christopher mcdonald happy gilmore The Cast of Happy Gilmore: Where Are They Now?


From the beginning, Shooter McGavin had it out for Happy Gilmore (Adam Sandler). He saw Gilmore’s violent outburst as harmful to the sport and fought vehemently to get him removed from the tour. Backed by fame and a legion of fans, the rock star pro’s ego made him an undeniably entertaining villain. After outbidding Gilmore for his grandmother’s house, he agrees to one final wager: If he beats Gilmore, the ill-tempered wannabe hockey player must quit the tour forever. If he loses, Gilmore gets the house back. In a predictable ending, Gilmore wins and McGavin throws the temper tantrum to end all temper tantrums.

McDonald was already established before the movie was released. That same year, he had six other films released including Celtic Pride and House Arrest. While he hasn’t achieved major movie star status like others in the film, he has consistently worked for the last four decades with roles in films like The House Bunny and Fanboys. He also ventured into television with guest roles in Without a Trace, The Twilight Zone and Beware the Batman as the voice of Harvey Dent. He currently has 7 projects either completed, in post-production or filming.

1. Adam Sandler – Happy Gilmore


Happy Gilmore was an aspiring hockey player with a heck of a slapshot and a short temper. When movers repossess his grandmother’s (Frances Bay) furniture for owing $270,000 in back taxes to the IRS, Gilmore wins money on a bet hitting golf balls with said slapshot. This gives him the idea to hustle other golfers at a local driving range so he can make some money to help her keep the house and he ends up running into club pro Chubbs Peterson (Carl Weathers). After winning a local tournament and earning a spot on the Pro Golf Tour, Gilmore’s unorthodox attitude made him the enemy of fellow pro Shooter McGavin (Christopher McDonald) who tries to get him removed from the tour. In a reversal of roles, he learns how to control his temper (not before getting into a fist fight with Bob Barker) and defeats McGavin, who throws a major temper tantrum in the end.

Unlike Gilmore, Sandler was already an established comedian by the time Happy Gilmore was released but the movie did help turn him into a legitimate star. The sports comedy was the second in a string of profitable films by the Saturday Night Live alum. Others include 1995’s Billy Madison, The Wedding Singer and The Waterboy in 1998 and Big Daddy in 1999. Sandler also ventured into drama with films like Punch-Drunk Love, Spanglish and Funny People. In 1999, he started Happy Madison Productions, which has produced a number of movies including The House Bunny with Anna Farris and Grown Ups with Kevin James, Chris Rock, David Spade, Rob Schneider, Salma Hayek and Maya Rudolph.

Despite box office success, Sandler’s movies remain critically panned. Roger Ebert gave Happy Gilmore one and a half stars and called the title character a “violent sociopath.” In December, it was announced he had signed a 5-movie deal with Netflix. The first, a western called The Ridiculous 6, became the most viewed film on the streaming service even after the controversy that saw dozens of Native Americans walk out on the production because of offensive stereotypes. He can next be seen in The Do Over with Paula Patton, David Spade and nephew Jared Sandler.

Has anyone else from the movie popped up anywhere interesting in the past 20 years? Let us know in the comments!