During scenes involving Richard Kiel, 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.
Before his first tournament, Happy asks Chubbs why he didn't play a real sport, "like football, or somethin'." Carl Weathers, who played Chubbs, was a professional football player before becoming an actor.
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 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 a 2011 interview with the AV Club, Christopher McDonald claims he originally turned down the role of Shooter 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 Adam 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.
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 lines "Grizzly Adams did have a beard.") Nick Faldo is mentioned, but never seen on screen.
To help promote the movie, Adam Sandler made a cameo appearance on "The Price Is Right" during the "Showcase Showdown". The clip of Sandler fighting "PIR" host, Bob Barker was shown to the studio audience.
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 US Open, the Open Championship, and the PGA Championship) where the winner gets a green jacket.
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.
Julie Bowen and Kevin Nealon both started in Happy gilmore and would later work together on 'Weeds', though they did not share any scenes in Happy Gilmore, Bowen played the brief target of Nealon's character 'Doug's affections.