How many fictional characters have had more of an impact on a sport than Happy Gilmore? Before the Adam Sandler comedy, golf was viewed as a luxury sport reserved for the wealthy and entitled. The game’s slow pace, strict etiquette, and expensive fees gave golf the reputation of a rich man’s game. Look how golf has changed in the 30 years since Happy Gilmore, from relaxed wardrobes and affordable courses to increased marketing and inclusive encouragement. Unfortunately, Timberland boots on the course never caught on.
Nearly 30 years after the original, Sandler dons his favorite Bruins jersey and heads to the golf course in Happy Gilmore 2. In the sequel, Happy lost most of the joy in his life, especially in the game that saved him. When his young daughter needs money to attend an illustrious dance school, Happy grabs his clubs and returns to the sport he once loved, though things have changed in his absence.
Ahead, director Kyle Newacheck explains the moment on set when Sandler’s performance gave him chills. The Workaholics co-creator also reveals what it was like to direct professional golfers and the athlete who surprised him the most on set.
This interview has been edited for length and clarity.
Digital Trends: You directed Happy Gilmore 2. Adam calls you up and says, “Kyle, I want you to direct another sequel to one of my movies, and I’m going to let you pick.” What are you taking, and why?
Kyle Newacheck: Little Nicky.
Why’s that?
I don’t know. I think it’d be fun. I think it would be wild. I think right now, you could make a wild version of Little Nicky.
That is definitely a good one. I like the idea of something that maybe wasn’t as critically or commercially successful and getting to go back into that and re-explore stuff.
I do, too. I think going into the little niche hallways of the Sandler-verse would be really fun.
I was reading an interview you did about this movie. You said that Happy brings people together, and that’s clearly a direct result of Adam. You’ve directed him in two movies. What makes Adam so undeniable as an actor?
He cares about people. He puts everybody else around him first. He cares about how they feel. He is a selfless individual. He knows how to make people laugh. He just knows. It just comes out of him. You’re not going to sit next to Sandler for longer than three minutes before something is going to make you just laugh your ass off. That’s him. I do think he is connected with the culture in a way … he just cares about it.
When was the first time you met him [Sandler]? Take me through that interaction. What was it like?
Oh my gosh. The first time I met Sandler must have been at the office when I was prepping Murder Mystery. I remember. He comes in, and he’s like, “Hey, how you doing?” I’m like, “What’s up?” He’s like, “You’re Kyle? You’re big. You’ve got wide shoulders. You play sports?”
So immediately, it goes to the coach and the team and how that works. Noticing you and figuring out where you go [laughs] and all that in this … I’ve hung out with him so much since. Every time, it’s just fun. It’s fun.
Ever get him on the pickleball court?
I keep telling him, dude. I keep telling him. He’s worried he’s going to hurt himself.
The guy’s playing basketball all the time.
That’s what I say. I say I think this is a little bit lighter than basketball, dude. But truth be told, I’m pretty deep in pickleball, and it’s a brutal sport when you get into it.
I believe you. I want to go back to the day on set when Adam steps onto the course in the tournament. He’s wearing the Bruins jersey, the sweatpants, and the boots. He performs that iconic swing. What was that day like for you and the entire crew watching Adam transform into this iconic character for the first time in nearly 30 years?
I mean, I have, like, probably one-third of the chills on my arm right now that I had when it actually happened because it’s magic when you see him put on the Bruins jersey. For me, I had been looking at the Bruins jersey and looking at the character’s wardrobe for a little bit. You’ll see we try to vary it up a little bit in the movie, which is cool.
For me, it was the Timbs [Timberland boots], dude. The Timbs brought it all to life. That was the original character choice of Happy Gilmore that really made it for me. There wasn’t a scene that we did where he didn’t have the Timbs on. That’s the character to me. It’s the Timbs. Timbs on the golf course? That’s the coolest thing you can do. The hockey jersey — I’ve seen some people play with hockey [jerseys] nowadays. I’ve never seen anybody golf in Timbs, even now.
And he [Sandler] wears them like a true Timbs wearer. It’s not fully tied. He flaps them over a little.
Slips ’em on. Slips ’em on. Yeah, dude.
There are so many cameos in this movie that I lost track. It’s insane, but in a great way, especially with the golfers. There’s that scene — a dinner — where it’s pretty much all golfers and not a lot of actors. What was it like directing the golfers?
Man, that was incredible — incredible! — to have that one scene where you have 10 of the greats, like five of the absolute greats, sitting at a table with Adam Sandler. The energy that came off of it, I could feel it. I could feel it. When we started getting going, those guys came to deliver lines. They did a really good job. They really did. That was incredible.
Sir Nick Faldo, Lee Trevino, Jack Nicklaus, Fred Couples, and then Adam Sandler at one table? Then you got Xander [Schauffele], Ricky [Fowler], Jordan Spieth, Keegan Bradley, Colin Morikawa. Then you got Bad Bunny and Travis Kelce, and this is one room.
Crazy.
It was one room, and I remember just running around, running around between everybody, saying, like, “You good? How you feeling? OK, let me hear that. Yeah, good. OK. Cool.” Just moving around and trying to keep the vibe right.
Who surprised you the most out of the golfers? Was someone coming up to you like, “I need notes for this line. I need a lot of direction.”
You know who had a natural delivering ability? Jack Nicklaus. Like, he did good. [Laughs] Every time he would give a little shrug, almost like he was on stage. And I’m like, I could see this guy in a sitcom. He was really surprising. I also think I was surprised how much I fell in love with John Daly. Like on a real level.
How can you not?
I know. I know. I just knew I was gonna really like him. I could just tell when he showed up; his whole being is a beautiful man. Beautiful.
Happy Gilmore 2 premieres on Netflix on July 25.
