Bob Barker wasn't sure if he wanted to be in the movie. When he learned that he was going to win the fight with Adam Sandler, he accepted the role.

When Dennis Dugan told Bob Barker that a stunt double would be used in the fight scene, Barker insisted on doing his own stunts, saying, "Wait a minute, I know how to fight."

During scenes involving Richard Kiel (Mr. Larson), he had to stand still or lean on items. In one scene it's a fence, in another it's another actor. This was due to a severe automobile accident he had in 1992 where he suffered head trauma, losing his ability to balance without aid.

In a 2011 interview with the AV Club, Christopher McDonald claims he originally turned down the role of Shooter McGavin several times because he was growing tired of being typecast as an antagonist. He reconsidered playing the role, as he had enjoyed Adam Sandler's previous film Billy Madison (1995) and while he was playing a golf tournament in Seattle while taking a break from filming his previous movie in Vancouver. Realizing that he was playing an antagonist in a comedy, and having been satisfied with the script, he asked for an arrangement to be made so he could meet with Sandler to discuss the movie. Upon their first meeting, McDonald ultimately decided to accept the role and has said it remains one of the best decisions of his career.

Adam Sandler's favorite role and movie of his own.

Bob Barker studied Tang Soo Do for decades under Chuck Norris and his brother Aaron Norris.

Ben Stiller took an uncredited role as the nursing home orderly. He's never called by his name by any of the characters, but his name tag says "Hal L".

The concept was inspired by Adam Sandler's childhood friend Kyle who was a hockey player. Kyle regularly played golf with Sandler and Sandler's father. Kyle is now a teacher in Manchester, New Hampshire (Sandler's home town) and coaches the high school hockey team.

In real life, Adam Sandler is terrible at both hockey and golf.

Before his first tournament, Happy asks Chubbs why he didn't play a real sport, "like football, or somethin'." Carl Weathers (Chubbs) was a professional football player before becoming an actor.

Because of Bob Barker's cameo, ratings for The Price Is Right (1972) rose considerably amongst college-age viewers.

According to Adam Sandler, Christopher McDonald had difficulty believing Shooter would be afraid of fighting Happy due to his size advantage. MacDonald is 6'3" while Sandler is 5'10". They debated for a while until Sandler convinced MacDonald that Shooter was afraid of Happy's violent temper.

The only two true PGA golfers in the movie are Mark Lye (the golfer who talks to Happy at the cocktail party) and Lee Trevino (the silent golfer who shakes his head in disbelief, only saying the line "Grizzly Adams did have a beard.") Nick Faldo is mentioned, but never seen on-screen.

The NHL Shop has sold hockey stick putters for many years.

To help promote the movie, Adam Sandler made a cameo appearance on The Price Is Right (1972), The Price Is Right: Episode #24.98 (1996) during the "Showcase Showdown". The clip of Sandler fighting host Bob Barker was shown to the studio audience.

Julie Bowen later revealed on Access Hollywood that there is a deleted segment of the Happy Place scene where she made out with the dwarf dressed like a cowboy.

Was the very first winner of the MTV Movie Award for Best Fight.

The hockey player Happy mentions in the beginning of the film is Terry O'Reilly. Once during a game, he jumped into the stands at Madison Square Garden and fought with a fan.

This film was rewritten by Judd Apatow, which went uncredited.

German golfer Martin Kaymer tried a Happy-style approach during the long drive competition at the 2015 PGA Championships.

The script called for an immediate scene transition after Happy slugged Bob Barker, but then they got the idea to turn it into a full-blown fistfight instead.

The first of many Adam Sandler movies directed by Dennis Dugan who also plays the character Doug Thompson.

Happy's shaggy homeless caddy (Allen Covert) is named Otto in the credits. This name is spoken in a deleted scene, but never in the main feature.

Bruce Campbell auditioned for the role of Shooter McGavin.

In 2016, Verne Lundquist stated he still gets a monthly $34 check from the Screen Actors Guild for his appearance in the film.

The guy who says "Grizzly Adams did have a beard" is Lee Trevino, one of the all time great golfers

During the mini golf scene Adam Sandler provided the voice of the laughing clown.

At many points in the film, Chubbs can be seen wearing Lacoste clothing, obviously as a link to the fact he lost his hand to an alligator.

This movie, as well as the rise of Tiger Woods around the same time, were pointed to as reasons for the surge in popularity of golf among younger demographics in the late 1990s-early 2000s.

Joe Sakic of the NHL's Colorado Avalanche appears uncredited during the hockey tryout scene.

Within the recurring commentary team that's seen throughout the tournaments, the co-commentator Jack Beard never speaks.

In a 2021 interview with NBC Sports, Christopher McDonald revealed that he modeled the character Shooter McGavin after golfing legend Greg Norman.

The hockey game in the opening scene features the now defunct Roller Hockey League's Vancouver Voodoo.

Verne Lundquist filmed all his scenes in one day, on the same set, even when he was in "different" locations for the golf tournaments.

Gilmore's "bull dance", where he gallops down the fairway while miming riding his driver, was famously reprised by PGA Tour golfer Boo Weekley during his 2008 Ryder Cup singles match playing for Team USA against England's Oliver Wilson playing for Team Europe at Valhalla Golf Club in Louisville. Weekley replicated it after his tee shot on the first hole and went on to defeat Wilson 4 & 2, with Team USA winning by 16½ to 11½ for their first Ryder Cup victory since their famous comeback in 1999.

Around 30 minutes of the film were cut in order to obtain the PG-13 rating.

Happy's car is a 1973 Plymouth Duster.

Originally Happy Gilmore was supposed to fight Ed McMahon but when Adam Sandler and director Dennis Dugan offered a role to McMahon he declined because of the film's profanity and crude humor. Sandler then re-wrote the role for Bob Barker who agreed to appear in the film.

Kevin Costner was offered the role of Shooter McGavin but declined. However, he did play a golf pro in Tin Cup (1996).

Mr. Larson is described as "Frankenstein" at one point. Richard Kiel played the Frankenstein monster in The Monkees: I Was a Teenage Monster (1967).

Early on, they considered obtaining the PGA or USGA license, but passed due to the high costs and likelihood of the script being rejected by both.

When Happy trains with Chubbs at the miniature golf course, the first hole is surrounded by penguins that terrorized him in Billy Madison (1995).

In October 2017, Christopher MacDonald was arrested for drunk driving. McDonald was driving in the Lake Arrowhead area on a Saturday night when he drove his classic silver Porsche off the highway, taking out a gas meter at Stater Bros. and ended up in an embankment. Before cops took him into custody, McDonald pulled the celebrity card telling them, "I was in 'Happy Gilmore'." They were not impressed. McDonald was taken to a nearby jail where he was kept until he sobered up. He was released without bail.

Adam Sandler initially offered the role of the nursing home orderly to Rob Schneider. Schneider turned it down because he wanted Sandler to use more famous people and not always rely on his friends to play all the characters in his movies.

Early in the movie, Chubbs tells Happy he could win a gold jacket, to which Happy responds, "Gold jacket, green jacket, who gives a shit?" This is a reference to The Masters, one of the four major tournaments of the PGA tour (the others being the U.S. Open, the Open Championship, and the PGA Championship) where the winner gets a green jacket.

Adam Sandler and Christopher McDonald went on to later appear in Dirty Work (1998), with McDonald also playing the antagonist in that film. While they both have the majority of screen time together in this movie, they share no scenes together in the latter film.

When Happy makes his Subway commercial, they are cutting their bread the original way. V shape down the middle which started the change over to the hinge in 1999.

Tim Allen was considered for the role of Shooter McGavin.

Lee Trevino said that had he read the script and seen the salty language, he would've passed.

In real life, the PGA does have a tournament called The Tour Championship. It is played annually in September, at East Lake Golf Club in Atlanta, and is the final event of the FedEx Cup Playoffs. Unlike its movie counterpart, however, it is not considered one of golf's Major championships, and the winner does not take home a gold jacket.

During the miniature golf sequence when happy destroys the clown out of frustration the laughing sound the clown makes was provided by Adam Sandler

In the Waterbury Open scene, Chubbs is seen wearing a Lacoste v-neck jumper with a logo of a crocodile, very similar to Chubbs' nemesis the alligator.

Adam Sandler, Ben Stiller, Allen Covert (Otto), and Joe Flaherty (Jeering Fan) all appeared on the sitcom The King of Queens (1998). Sandler's appearance was uncredited. Stiller's appearance was uncredited on that sitcom as it was in this film. Covert played 2 different characters on that sitcom. Flaherty had a recurring role on that sitcom as the priest, Father McAndrew.

Earlier in the film when Chubbs is trying to convince Happy Gilmore to play golf, he refuses, saying "Golf requires goofy pants and a fat ass." Later in the film Chris McDonald's character is seen with padding in his pants as he walks away.

When Happy arrives at the Waterbury Open, he notices a white limousine pulling up behind him and says "Whoa, must be Burt Reynolds or something." Adam Sandler later worked with Burt Reynolds nine years after Happy Gilmore (1996) in The Longest Yard (2005), which was a remake of The Longest Yard (1974), in which Burt Reynolds previously appeared. And, Richard Kiel, who was also in Happy Gilmore, played in the original film The Longest Yard

Both Richard Kiel (Mr. Larson) and Frances Bay (Grandma Gilmore) would later star together in Inspector Gadget (1999).

Both Julie Bowen(who plays Adam Sandler's love interest in this movie) and Richard Kiel were both in Tangled(2010),Rapunzel Tangled Adventure(2017-2019)

Steve Guttenberg was briefly considered for the role of Shooter McGavin but he agreed to do It Takes Two (1995) at the same exact time and turned down the role.

Joe Flaherty plays the character of the 'Jeering Fan', who drives into Happy with a white Volkswagen beetle. Flaherty had previously appeared in the film "Sesame Street Presents: Follow That Bird" (1985), where a yellow Volkswagen beetle figured prominently into the plot.

Julie Bowen and Kevin Nealon appeared in Weeds (2005). Bowen played the brief target of Nealon's character Doug's affections.

Happy tells Virginia that his grandmother (Frances Bay) took him to see the film "Endless Love" (1981) starring Brooke Shields. Frances Bay and Brooke Shields both had recurring roles on the ABC sitcom 'The Middle' (2009-2018): Bay as Aunt Ginny and Shields as Rita Glossner. The Middle (2009) also premiered on the same night and the same network as Julie Bowen's sitcom Modern Family (2009).

In this film, Frances Bay appeared on-screen with Ben Stiller. Bay also appeared in the 1998 series finale of Seinfeld (1989), as did Ben Stiller's father, Jerry Stiller (in his recurring role as Frank Costanza).

This movie and Employee of the Month (2006) feature one of the actors singing the song "Kiss You All Over" by Exile (1978). It also is featured in Man on the Moon (1999).

David Hasselhoff is mentioned twice by Shooter McGavin in this film. Adam Sandler would later star in Click (2006), with David Hasselhoff who plays his boss.

Italian censorship visa # 91749 delivered on 5 June 1997.

One deleted scene in the movie involves Happy throwing the nursing home orderly out the window after finding out how badly his grandma was treated.

In an interview with Vulture, Christopher McDonald has stated that he had attempted to work with Adam Sandler in other films following Happy Gilmore by auditioning for roles in his films but always ended up not getting the role. According to Christopher, Adam's response is always the same which is "dude, you'll always be Shooter."