The list of golf comedies is rather on the lean side, and while Caddyshack will likely forever be the top champ, Happy Gilmore can certainly lay claim to its fair share of memorable moments. While infinitely more sophomoric than Caddyshack, its story of a struggling hockey player turned pro golfer helped solidify Adam Sandler as the standout of his SNL class.
While Sandler was the movie’s star, it was the supporting cast that provided many of the most memorable moments. From Bob Barker’s fist fight to Carl Weathers’ phony hand, Happy Gilmore always had the right club for whatever the scene required. It seems like a good time to check in and see what the cast has been up to since Happy ricocheted his putt off a fallen TV tower to win the tournament.
Christopher McDonald as Shooter McGavin
Before playing arrogant golf pro Shooter, Christopher McDonald had made a name for himself playing jerks in movies like Thelma and Louise, Fatal Instinct, and Grumpy Old Men. In Happy Gilmore, of course, Shooter went on to likely be murdered by Mr. Larson, but McDonald would continue as a much sought-after character actor working on popular shows like The Sopranos, Boardwalk Empire, Happy Endings and 2015’s Western miniseries Texas Rising. In addition to filming his recurring role on the final season of The Good Wife, McDonald worked on the crime drama Jekyll Island with Minnie Driver and Mary McCormack.
Allen Covert as Otto
It’s not easy to recognize regular Happy Madison actor Allen Covert behind the long hair and beard as Happy’s disheveled homeless caddy. Covert had previously appeared with his buddy in both Airheads and Billy Madison, and Happy Gilmore would be only the third of the many movies that the actor, writer, and producer has worked on with Adam Sandler over the last 20 years, with highlights including significant screen time in The Wedding Singer, Big Daddy, and the Sandler-produced Grandma’s Boy, in which Covert played the lead. Besides his work with Sandler, Covert also works as a founder and author of Cherrytree Books, a company that specializes in children’s literature for the iPad.
Carl Weathers as Chubbs
Former Oakland Raiders linebacker Weathers had appeared in mostly action movies like the Rocky franchise and Predator before Adam Sandler came along and helped him start his foray into comedy. Besides working with Adam Sandler (reprising the role of Chubbs for Little Nicky and providing the voice of a water bottle in the animated movie, Eight Crazy Nights), Weathers has appeared in episodes of Arrested Development, The Shield, and he has a recurring role on the USA sci-fi drama, Colony.
Kevin Nealon as Garry Potter
Surprisingly, Kevin Nealon was the only other ’90s SNL cast member to show up in Happy Gilmore — though it does also feature SNL writer Robert Smigel as an IRS agent. The veteran stand-up would go on to reunite with Adam Sandler in The Wedding Singer and Little Nicky in addition to working on projects with former SNL cast members like David Spade in Joe Dirt. Nealon’s worked steadily over the years with both regular roles in shows like ‘Til Death and Weeds, as well as smaller parts like his portrayal of Chuck Falcon in The League. Nealon still tours comedy clubs and theaters regularly and is an active supporter of several charities.
Julie Bowen as Virginia Venit
Julie Bowen’s role in Happy Gilmore provided a springboard for a part in Multiplicity and recurring parts in TV shows like ER, Lost, and Weeds. Bowen is best known these days for playing Claire Dunphy on Modern Family, a role that has nabbed her two Emmy awards. Additionally, Bowen has popped up in Horrible Bosses, Family Guy and the Adult Swim cult favorite, Children’s Hospital.
Francis Bay as Grandma
Canadian actress Francis Bay played Happy’s sweet, tax-cheat grandmother whose financial hardship pushes Happy onto the links. Bay didn’t start her acting career until she was into her fifties, landing her first TV role on Mary Tyler Moore and following it up with parts in The Dukes of Hazard and The Jeffersons. Bay would regularly work in TV and film throughout the ’80s and ’90s, appearing on Cheers, Newhart, ALF, and playing marble rye nemesis to Jerry Seinfeld as recurring character Mrs. Choate on Seinfeld. Bay passed away at age 92 in 2011.
Richard Kiel as Mr. Larson
An imposing figure, Richard Kiel was best known for playing steel-chomping James Bond villain Jaws in The Spy Who Loved Me and Moonraker, but worked as a math teacher before taking up acting. The seven-foot giant and took on a variety of villainous parts in movies like Inspector Gadget and lent his voice to the 2010 Disney movie Tangled. Kiel passed away in 2014 at the age of 74.
Bob Barker as Himself
Bob Barker arguably provided one of the best cameos of the ’90s when he played himself and engaged in fisticuffs with Happy on the golf course. The longtime host of The Price is Right retired from telling people to “come on down” in 2007, and has remained an active advocate for longtime animal charities like PETA and the Humane Society.
While the 92-year-old former TV host might not be clocking in to the CBS lot five days a week, he’s stayed plenty busy lending his voice to Family Guy and Futurama, and occasionally visiting his old game show stomping grounds. Probably his most notable appearance of late came when he revisited his grudge against Happy during the Night of Too Many Stars special.
Ben Stiller as Hal L.
Ben Stiller didn’t have a huge role in the movie, but his take on the two-faced a-hole at Happy’s grandmother’s nursing home remains one of his best cameos. Stiller already had success in TV shows like The Ben Stiller Show and movies such as Heavyweights prior to offering Happy’s grandmother “a warm glass of shut the hell up.” Stiller finished up the ’90s starring in comedy classics like There’s Something About Mary and went on to direct and star in box office hits Zoolander and Tropic Thunder. Stiller has also starred in Meet the Parents and its sequels, as well as the Night at the Museum movies.
If it wasn’t evident by his IMDb resume, Stiller’s cemented his place as one of Hollywood’s most reliable comedic actors, and most recently revived fan favorite Derek Zoolander with the (not incredibly successful) release of Zoolander 2.
Adam Sandler as Happy Gilmore
Sandler already had his first post-SNL movie hit a year earlier with Billy Madison and again teamed up with former SNL scribe Tim Herlihy (who has now written 11 Sandler movies) on Happy Gilmore. The movie would also be Sandler’s first in a series of eight screwball comedies that he starred in with Dennis Dugan as director.
Happy Gilmore might be Sandler’s most-loved movie, and he’s followed it up with box office hits like The Waterboy, Big Daddy, The Wedding Singer, and 50 First Dates. The 2000s saw the actor branch out from his slapstick humor to drama, appearing in Punch Drunk Love, Reign Over Me, and former roommate Judd Apatow’s dramedy Funny People. The Grown Ups star recently teamed up with Netflix for the western comedy The Ridiculous 6 (which he co-wrote with Herlihy) and with SNL buddy David Spade in The Do Over.