What The Happy Gilmore Cast Looks Like Today

Actor, writer, comedian, and producer Adam Sandler has had a lot of ups and downs over the years, creating a few critically acclaimed movies but also releasing several projects that were almost universally panned by critics and fans alike. One thing that everyone can largely agree on, however, is that "Happy Gilmore" is one of Adam Sandler's best comedy movies and is fondly remembered by fans of '90s comedies.

Following directly from the success of "Billy Madison," this tale of a hockey player who turns to golf after discovering he can drive the ball more than 400 yards established Sandler as a bankable comedy star. The story sees Gilmore becoming a professional golfer in an effort to rescue his grandmother's repossessed house. Along the way, he competes in a variety of championships while facing off against his new nemesis, Shooter McGavin.

With the movie launching in theaters way back in 1996, it might surprise you to learn just what the cast looks like today. Many of the actors involved in the film have gone on to bigger and better things in the more than two decades since it was released, but all of them look very different to when they appeared in "Happy Gilmore."

Every good hero needs a villain to battle against, and Christopher McDonald provided that in "Happy Gilmore." The actor played pro golfer Shooter McGavin, a man determined to keep golf free from Gilmore's wild antics and get his hands on the fictional — but highly coveted — gold jacket. As one of the top athletes on the pro tour, McGavin goes to extreme lengths to enforce golf etiquette and ensure that Gilmore doesn't succeed in winning the prestigious Tour Championship. He even goes as far as hiring a heckler to distract his rival on the golf course.

Before the actor was cast in the 1996 comedy, he was known for roles in acclaimed films like "Thelma and Louise" and "Quiz Show." He had a history of playing villains, along with credits in "Grease 2," "The Boys Next Door," and "Grumpy Old Men." After "Happy Gilmore," McDonald appeared in the likes of "Requiem for a Dream," "Flubber," and "The Faculty" before turning up in more recent movies such as "American Pie Presents: The Naked Mile" and "Deep in the Valley." In recent years, he has kept busy with recurring roles on the television shows "Ballers," "Hacks," "The Watcher," "Secret Invasion," and the third season of "American Crime Story" tracking the Bill Clinton and Monica Lewinski sex scandal.

Before appearing in "Happy Gilmore" as Happy's golf coach and mentor Chubbs Peterson, Weathers was a familiar face in a wide range of Hollywood movies. The biggest roles of his early career were as Dillon in "Predator" and Apollo Creed in the "Rocky" movies. Before acting, he played professional football for the Oakland Raiders, appearing in eight games before being released.

After "Happy Gilmore," Weathers continued his acting career and even reprised his role as Chubbs in the 2000 movie "Little Nicky" with Sandler. He then went on to play a fictional version of himself who helps tutor Tobias in the sitcom "Arrested Development." As a voice actor, he has portrayed Combat Carl in the "Toy Story" series across various movies, television series, and specials, and later voiced Omnitraxus Prime in "Star vs. the Forces of Evil." Over the years, Weathers has continuously branched out into other mediums including web series, music, and even video games like "The Artful Escape" and "Mortal Kombat X," the latter of which found him reprising his role from "Predator" for a special DLC skin. Most recently, he has been a pivotal part of "The Mandalorian" as Greef Karga in all three seasons of the show thus far.

Although he's uncredited, Ben Stiller has a relatively large role in "Happy Gilmore" as Hal L. This character is a cruel and devious orderly who works at the nursing home where Gilmore's grandmother moves after leaving her repossessed house. While he outwardly appears warm and kind at first, it is later shown that he takes advantage of the elderly residents under his care, forcing them to work for him.

Stiller's uncredited role in "Happy Gilmore" might have been somewhat surprising, considering that the actor had appeared in a number of movies in the late '80s and early '90s and even had his own television series in the form of "The Ben Stiller Show." Yet Stiller and Sandler were both comedians who started on "SNL," and have even admitted in an interview with USA Today that fans often confuse the pair. Stiller later reprised his role as the orderly in the 2020 movie "Hubie Halloween."

After "Happy Gilmore," Stiller became one of the biggest names in comedy, writing and starring in films such as "Zoolander," "Dodgeball," "Meet the Parents," and "Night at the Museum." He also voiced Alex the lion in the "Madagascar" animated film series and directed "The Secret Life of Walter Mitty" in 2013. Over the course of the last few years, he has largely remained behind the camera, working as a director and producer on numerous television and movie projects.

Although fans of "Happy Gilmore" will recognize Dennis Dugan from the movie, he played a far bigger role than simply portraying one of the characters. In addition to playing Doug Thompson, the commissioner of the Pro Golf Tour and the man who decides the fate of Gilmore, Dugan actually directed the flick. Speaking to The Independent in 2013, he revealed that he got the job of directing the movie after previously trying to hire Sandler for another project he was shooting.

This first collaboration between Dugan and Sandler would not be the last. "Happy Gilmore" sparked a relationship that has lasted three decades, with Dugan directing many Happy Madison Productions films. These have included "Big Daddy," "Grown Ups," "Jack and Jill," and "You Don't Mess with the Zohan." He has also appeared in several of these projects in minor roles. In 2020, he directed and co-wrote the romantic comedy "Love, Weddings and Other Disasters," although it went on to gross just $900,000 worldwide, according to Box Office Mojo.

From 1972 until 2007, Bob Barker was the host of the television game show "The Price is Right." As one of the most recognizable men on TV in the United States, it may have shocked some people to see him appear in "Happy Gilmore." The presenter plays a fictionalized version of himself who teams up with Gilmore in the Pepsi pro-am event. When Donald manages to put Gilmore off his game, he and Barker get into an argument that ends up in a fight. The confrontation between the pair won the 1996 MTV Movie Award for Best Fight.

Barker continued to present "The Price is Right" for more than a decade after "Happy Gilmore" was released, before retiring after 50 years in television, according to Reuters. However, he has made some special guest appearances on the show and worked on other projects, such as an autobiography that was released in 2009. He has also been involved in commercials for various companies and even made a guest appearance on an episode of "SpongeBob SquarePants," where he played a snail rescue center operator known as Bob Barnacle (via Yahoo!).

Lee Trevino is a former professional golfer who was well known for not only being a great athlete but also a witty person. He could entertain viewers with his play and humor, so it makes sense that the producers of "Happy Gilmore" would come knocking on his door when they wanted a pro golfer to add to the cast and lend some credibility. Trevino won six majors during his career, coming first twice in the U.S. Open, The Open Championship, and the PGA Championship.

He appears as himself in the movie, often showing up for just a few moments to shake his head and disapprove of what Gilmore is doing. While Trevino's part in the film was inoffensive, he later revealed that he regretted doing the movie. Speaking at the University of Texas in 2013, he said (via the LA Times), "If [I'd known] they were going to use all those foul words in there, I never would have done it."

In an interview with Sports Illustrated, he confirmed that he still plays golf regularly and takes part in events. While he has tried broadcasting and other jobs, his love of golf keeps him playing the sport rather than doing other things.

Richard Kiel appeared in the 1970s James Bond movies "The Spy Who Loved Me" and "Moonraker" as Jaws, arguably one of the greatest villains in the history of the 007 franchise. During the height of his career, he also had roles in "The Longest Yard" and "Silver Streak" but found new fame after portraying Mr. Larson in "Happy Gilmore." Larson is Gilmore's former boss and someone who looks out for him as he becomes a professional golfer, threatening McGavin several times throughout the movie.

"Happy Gilmore" ended up being one of Kiel's final roles. According to Reuters, he largely retired from acting after suffering injuries in an auto accident. However, he did appear in "Inspector Gadget" as a parody of his Jaws character in 1999. His last major role came in 2010, when he provided the voice for the character of Vladimir in the Disney animated movie "Tangled." He passed away in 2014 from a heart attack at the age of 74.

Ken Camroux-Taylor — credited at the time as just Ken Camroux — played the role of Happy's hockey coach who cuts him from the team and subsequently gets beaten up near the start of the film. Camroux-Taylor is a hard-working character actor who has been working steadily since the beginning of the 1970s. He has racked up over 130 credits over the years, mostly in minor supporting roles.

"Happy Gilmore" is still probably one of his most recognizable roles, but he has also been in big movies and TV shows like "The X-Files," "The Outer Limits," "Saving Silverman," and "Reindeer Games." One of his most prominent performances in recent years was on CW's "The Flash" TV series. He played the recurring supporting role of Judge Hankerson in Seasons 3 through 6. His time on the series ended in 2019, and he has only been in a couple of projects since. Camroux-Taylor's latest role to date was in a 2021 episode of the Netflix original series "Firefly Lane," in the bit part of an unnamed pharmacist.

Nancy Hillis played Terry, Happy's girlfriend who dumps him on the same day he is cut from the hockey team. Hillis went by the name Nancy McClure at the time of the film's release in 1996, but was also known by the name Nancy McGiffert, which she used when making her acting debut in 1991 with "If Looks Could Kill." Hillis hasn't acted all that much over the years, and "Happy Gilmore" has remained her largest feature film role. 

Most of her other roles were unnamed bit parts, playing an airline rep and a waitress in the made-for-TV movies "Nowhere to Hide" and "Convictions." She also worked briefly as a segment producer on the Nickelodeon game show "What Would You Do?" and served for a time as the personal assistant of Bobby Roth, a television director best known these days for his work on "Agents of S.H.I.E.L.D." and "Prison Break."

Just one year after "Happy Gilmore" was released, Hillis took an extended break from acting. For over two decades, Hillis lived her life outside of the entertainment industry altogether. She eventually made a surprise return to acting in 2018 with a role in the short film "Outage." Since making her return, she has continued acting on a sporadic basis. Her latest role, and also her biggest by far since "Happy Gilmore," was as Penelope Dearbon on two episodes of "The Flash."

Alongside Will Sasso, Dee Jay Jackson played the other mover who repossesses Grandma's belongings and gets Happy to try golfing for the first time. He had already been acting since the late 1980s with small roles in notable titles like "Look Who's Talking," but "Happy Gilmore" was the biggest film of his career at that point.

Jackson's career continued with similar small roles and bit parts over the years. Some of his most notable films and shows include "Screwed," "Agent Cody Banks," the animated series "RoboCop: Alpha Commando," the 2014 "Godzilla" reboot, "Smallville," "Slither," and "Scary Movie 3." Most of his roles have been small, but he has been in over 150 different projects throughout the course of his roughly 35-year career. He joined the cast of the CW's "Superman & Lois" in the first season and has stuck with the show since. In what is arguably the largest role of his career as Cobb Branden, Jackson remains an important part of the ongoing series.

Brett Armstrong played the more prominent of the villainous Shooter McGavin's two golf caddies. "Happy Gilmore" was only Armstrong's second acting role after appearing in the made-for-TV movie "Little Criminals" the prior year, but he was already working in the entertainment industry in other capacities. Armstrong was in a couple of other movies, including "Saving Silverman" and "Drone," but his acting resume is quite slim. It is clear that acting isn't and has never been his primary focus. Instead, that honor belongs to stunt work.

Since the beginning of the 1990s, Armstrong has worked as a stunt performer and coordinator. He has amassed an incredibly prolific body of work in the world of stunts and continues to work on several projects per year. He is rapidly approaching 300 total stunt credits with more on the way. Some of the biggest movies Armstrong has been involved in include "The Predator," "I, Robot," "Star Trek Beyond," and the last two installments in the modern "Planet of the Apes" trilogy, amongst plenty of others.

Joe Flaherty played the pivotal role of Donald, a fanatical Shooter McGavin fan who will do anything to get close to his idol. The pro golfer hires him to heckle Happy in an attempt to force him to lose his temper, so he will be kicked off the tour. By the end of the film, he is crazed enough to drive his car onto the course and hit Happy, injuring him in the final of the Tour Championship before crashing and getting set on fire.

Prior to appearing in "Happy Gilmore," Flaherty was known for being one of the main talents on the Canadian sketch comedy show "SCTV." He went on to appear in minor roles in a series of movies throughout the '80s. One of Flaherty's most recognizable roles was as Harold Weir in the 1999 series "Freaks and Geeks," where he was part of the main cast alongside the up-and-coming talents of Linda Cardellini, James Franco, Seth Rogen, Martin Starr, Jason Segel, and Samm Levine. He also played one of the leads on the short-lived "Police Academy: The Series," the television offshoot of the popular movie series. Flaherty continued acting steadily throughout the 2000s but his career was winding down by the start of the 2010s. His last professional production was a one-off appearance on an episode of the TV show "Call Me Fitz," and his final performance overall was in the six-minute-long 2014 short film "Nightlife" in which he played a vampire. Flaherty has been in retirement ever since.