In the latest episode of Boardroom Talks, Sandler and fellow cast members Julie Bowen, Christopher McDonald, and Benny Safdie discuss bringing the second film to life.
Writing a sequel to a cult classic is not an easy feat, especially if it’s a film still beloved three decades later. Not only is there pressure to make it culturally relevant, but also to maintain the same banter that initially attracted audiences. Well, not everyone is as gifted as Adam Sandler, because the funnyman accomplished just that and more with Happy Gilmore 2 on Netflix, a film that tugs at the heartstrings while also eliciting multiple belly laughs in 114 minutes.
If you haven’t seen the 1996 film, stop reading this and go to Netflix immediately before continuing. In all seriousness, the original was a classic ’90s production with comedic zingers that highlight the depths of Sandler’s wit. It takes on a life of its own, thanks to one-liners still used today — “You eat pieces of sh*t for breakfast?” — and the audience’s introduction to iconic characters, with whom we almost feel sorry for. (Well, maybe it’s just me who sympathizes with Shooter McGavin‘s ruthless attempts to earn his yellow jacket.)
The 2025 follow-up almost mirrors the same exact format, too. Rather than saving his grandmother’s house, Happy, now retired, decides to re-enter the competitive world of golf in order to pay for his daughter Vienna’s (played by his real-life daughter, Sunny) tuition to a prestigious dance academy in Paris. Dennis Dugan, the film’s original director, didn’t helm the sequel, but appears in the film. In fact, Sandler tells Boardroom he was still on set mentoring director Kyle Newacheck, who previously worked with Sandler on 2019’s Murder Mystery.
“He’s a great man, and Kyle loved Dennis. But he’s got a great youthful spirit, always in a great space, creates a nice, happy environment, loves comedy, knows comedy, and comes up with great thoughts. He came up with that thing when Happy’s on the municipal course and he’s not playing well, and he’s cursing, and we’re cutting out everything. He came up with that, and that was like, we were all like, oh yeah, that’s beautiful.”
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One of the cornerstones of the first movie’s success is the celebs who made guest appearances both for fun and to advance the plot. I mean, who can forget the epic fight scene between the late The Price is Right host Bob Parker and Happy, which ended in embarrassment for the latter?
Sandler upped the star power for the sequel, bringing together some of the best in sports and entertainment. Bad Bunny headlines the cast as Happy’s lovable caddy Oscar, who needs some gentle parenting every now and then but overall means well. His pushy boss at the prestigious country club is played by none other than Chiefs tight end Travis Kelce, who Sandler confirmed would have a role months ago. And if you blink, you might miss the moment, because the A-list guest stars include pro golfers Rory McIlroy, Scottie Scheffler, Justin Thomas, Brooks Koepka, and LPGA world No. 1 Nelly Korda, to name a few. Artists lending their talent include Cam’ron, Eminem, and Post Malone. Ben Stiller also returns to wreak havoc, while we get a Haley Joel Osment sighting, as well.
Sadly, not everyone introduced in the 1996 film reprises their role in this iteration. Carl Weathers, who plays Derick “Chubbs” Peterson, a former pro golfer and Happy’s coach and mentor, sadly passed away last year. Sandler confirmed that Weathers was alive when they started the script, so he and Tim Herlihy reworked the storyline to pay tribute to the late actor.
“We just rewrote it and made sure we showed him the love he deserves. Happy Gilmore, that was a long time ago, but we got tight on set and over the years. We’d see each other and we’d always say, ‘Still hear about Happy, man.’ That was, Bob said it, Carl Weathers, Joe Florida, everybody. We had this thing like, man, you still hearing about Happy Gilmore? That was the one that stuck out the most. So it was great to think of them while we made it.”
Boardroom spoke with Sandler, Julie Bowen (“Virginia Venit”), Christopher McDonald (“Shooter McGavin”), and Benny Safdie (“Frank Manatee”) on the film’s decades-long impact, possible spin-offs, and more in the latest Boardroom Talks. Happy Gilmore 2 is available now to stream on Netflix.
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