There were plans for Carl Weathers to return as Chubbs before his death in 2024. Adam Sandler said, "We had a painful change. Carl Weathers had a massive part. I would talk to Carl, and we were excited, and then Carl passed away. We had to rewrite a lot of the stuff, and even what the story was. We made a lot of nice references to how great Chubbs was in the movie. That was the biggest change."
This movie will be dedicated in memoriam to Bob Barker (self), Carl Weathers (Chubbs), Frances Bay (Grandma), Richard Kiel (Mr. Larson), and Joe Flaherty (Donald) who appeared in Happy Gilmore (1996).
Early in the film, when Happy first returns to a golf course to join a game, the attendants checking him in are watching a show featuring the late Cameron Boyce. Boyce, who played one of Adam Sandler's sons in Grown Ups, as well as its sequel Grown Ups 2, passed away in July of 2019.
The entire Sandler family makes appearances in this film. Sunny Sandler plays Vienna, his daughter in the movie. Her older sister Sadie Sandler plays Charlotte, a member of the support group. And Adam's wife Jackie plays Vienna's ballet teacher.
Happy's sons are all named after famous hockey players: Gordie (Howe), Wayne (Gretzky), Bobby (Orr) and Terry (O'Reilly).
Rob Schneider: as the Tricycle Cowboy in Happy's dream, yelling "You can do it!" Basically, Schneider is doing his "You Can Do It!" guy role that he has played in many Adam Sandler films.
Kelsey Plum: As the Municipal Starter. This role marks the WNBA star's acting debut, according to Bleacher Report.