Adam Sandler Plays Golf With Bryson DeChambeau and Mostly Gets Out of the Way

Adam Sandler has been doing the shooter fingers approximately forty times a day for thirty years. He did not ask for this. It just happened, the way most great things happen, which is that Tim Hurley came up with the name Shooter and then Christopher McDonald ran with it and now there is no escape. Sandler seems genuinely okay with this. He also seems genuinely okay with most things, which is either the secret to his longevity or just what a man looks like after decades of getting paid obscene money to play golf with his friends on camera.

Break 50 is Bryson DeChambeau’s YouTube show, the premise being that he and a partner attempt to shoot 23 under par in a two-man scramble. Episode four pairs him with Sandler, who recently finished shooting Happy Gilmore 2 and shows up in Curry basketball shoes with a stiff back and a 54-degree wedge he cannot stop pushing right. The goal is not really achievable. They end up at 21 under, one eagle and one birdie short. They do not seem devastated.

What makes this work, and it does work, is that Sandler is the rare celebrity guest who does not perform being a good sport. He actually is one. He calls his bad shots before anyone else can, he asks DeChambeau real questions about becoming a golfer, and when DeChambeau starts talking about not wanting kids to see him lose his temper on course, Sandler just nods and says you’re going to make mistakes throughout your life and set the wrong example on occasion, but what can you do. That’s it. No inspirational pivot. Just a shrug that lands like a point.

The Happy Gilmore Mythology Gets a Fact-Check

DeChambeau grew up watching Happy Gilmore five times a week, which is a thing he announces at the top of the episode with the sincerity of a man who means it. Sandler receives this information the way he receives most information, with mild amusement and then a segue. But he does give up some genuinely good production lore. Shooter McGavin’s last name was a tribute to Darren McGavin, who played Billy Madison’s father, because Sandler and Hurley always tried to tie their movies together with small connections. The first name came from Hurley. The fingers were all McDonald.

The only one we fight over who wrote what is he says ‘eats shit for breakfast.’ I think I wrote it and he thinks he wrote it. No way. We only argue over that one and we hear that line a lot on the streets.

The Cameron Boyce story lands harder. Sandler explains that the ‘chocolate wasted’ line from Grown-Ups was improvised by Boyce on the day, and that Sandler asked if it might be funnier coming from his little sister instead. Boyce, then a kid, immediately said yes. Sandler describes him as ‘like an old-timer just going whatever’s best for the movie.’ Boyce died in 2019 at nineteen. Sandler doesn’t linger. He says ‘anyways, this is us’ and they go back to golf, which is exactly the right call.

I just kind of lost in Happy Gilmore land.

The Scream Loosens Everything

There is a stretch in the back nine where DeChambeau is visibly tense, partly because they need eagles they are not making, partly because the show’s cameraman Chase keeps delivering the kind of passive-aggressive commentary that would get a caddy fired on any professional tour. Sandler diagnoses the problem immediately. He asks DeChambeau to yell as loud as he can into the woods. DeChambeau does it. He then hits one of the better three-woods of the round. Nobody is surprised.

The scream loosened everything.

Happy Gilmore 2 comes out July 25th. Sandler says it has a PG-13 rating, a lot of jokes, and a sweet family feel. He describes showing it to friends and watching them feel like youngsters again. DeChambeau, meanwhile, announces he is going to be an actor now, especially after Oakmont. Whether that is a threat or a promise depends entirely on your feelings about the US Open.

Nobody wants to connect with an asshole. So you try to not be an asshole too much.