Sandler, Shooter and me: What happened when I joined the 'Happy Gilmore 2' cast on the golf course

BEDMINSTER, New Jersey — After spending a day zooming around a country club in a golf cart, feeling the balmy breeze filter through my collared sweater vest, I saw the best thing I’d seen all day: Dozens of middle-aged golf tournament participants, clad in baseball hats and polo shirts, hollering “Shooter McGavin!” with unbridled joy.

From my perch on the back of the bougie vehicle, I could see actor Christopher McDonald in the cart ahead of me, beaming with joy as real-life golfers recognized him as the uppity villain he played in a movie that premiered 29 years ago, Happy Gilmore. On the greens of Fiddler's Elbow Country Club on July 13, the 1996 comedy about a belligerent failed hockey player who transforms into a golfer to save his grandmother’s home might as well be in theaters today.

I don’t think the real-life golfers knew this, but McDonald and I were there — along with Adam Sandler, Julie Bowen, Benny Safdie and a gaggle of other journalists — for a press event on behalf of Happy Gilmore 2, its long-awaited follow-up, which starts streaming on Netflix July 25.

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Any questions I had about why Happy Gilmore is one of the few Sandler characters to get his own sequel dissipated when I saw that crowd erupt. People aren’t just going to stream this movie because they love seeing familiar material rebooted and rehashed. They love this guy — the outsider who invaded their sport, messed it up and defeated the established Goliath of golf.

Earlier that day, I sat with McDonald and Safdie on a hill overlooking the course. They gushed to me about the timelessness of Happy Gilmore, excitedly quoting the original movie to each other as they talked about why it needed a follow-up film.

Safdie, who directed Sandler in a rare dramatic role in 2019's Uncut Gems, estimates that he’s seen Happy Gilmore hundreds of times. He told me he could close his eyes and watch the film in his mind from beginning to end, adding that it’s “one of the best, funniest movies there is.” Lines from the movie, like “five iron, huh? You’re fired.” — something McGavin mumbles to his caddy before letting him go — have become part of his daily lexicon.

McDonald was more straightforward. “Our fans demanded it,” he told me. Earlier that day, Sandler joked to me that “30 years of pressure from Shooter McGavin” is the main reason they got the gang back together at all.

Find your ‘happy place’

I felt out of place when I rolled into the country club parking lot that morning, my battered Subaru Impreza sticking out among BMWs and Cadillacs. I told the security guard what I was there for. He put his hands on his hips, mocking me as if I were the fancy one, then broke into a smile to share that he’d met Sandler during their New York University days. I might have been at a ritzy country club, but a few scenes from the sequel were filmed here, and this was Sandler’s domain.

Netflix gave the author some Happy Gilmore 2 merch. (Photo illustration: Yahoo News; illustrations; Jiaqi Wang for Yahoo News; photos: Kelsey Weekman/Yahoo News)

I took the portable neck fan Netflix had given me the night before at a screening, now smudged with the orange streaks of the makeup I sweated off, and hopped in a golf cart that took me to a driving range. There, a kind staffer handed me a Boston Bruins jersey and a hockey stick and invited me to try to put a golf ball into a hole. I could not do it in less than four swings, no matter how hard I tried or how close I stood, even after the country club’s staff professional gently encouraged me to “just tap it in.”

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I wanted to blast the ball into the stratosphere or drop to my hands and knees on the green and shriek, “That’s your home! Are you too good for your home?!” at the menacing little sphere, but I had to go meet Sandler. And my sweater vest was a rental item I couldn’t afford to cover in grass stains.

When I met the megastar, he was wearing an oversize polo shirt and shorts — in keeping with the country club’s dress code, but true to his signature style. Sandler’s laid-back demeanor instantly put me at ease as he fired off jokes and sipped from a venti Starbucks drink with his old pal, Bowen, aka Virginia Venit, the gorgeous PR director who quickly fell for Gilmore’s rough-around-the-edges style and became his “happy place.”

Their love anchors the original movie, so I was surprised when I heard Bowen say she didn’t expect to be in the sequel. She thought she might be replaced by a younger actress.

“My kids were like, ‘It’s never gonna happen for you, old lady!’” she told me, adding that Sandler didn’t owe her anything. Sandler rejected that, saying, “She was wonderful in it. Our characters love each other!”

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“In real life, I don’t love being near her so much,” he added, joking that their best day on set was when Bowen finally left.

Family matters

I was moved by how much the sequel was centered around family. Sandler and Bowen’s characters are still very much in love and have several sons and a daughter, played by Sandler’s real-life kid, Sunny. His daughter, Sadie, and wife, Jackie, also have roles in the new film.

Sandler told me the first time his real-life family was all together onscreen was in 2008’s Bedtime Stories — in one scene, Jackie is holding Sadie while pregnant with Sunny.

I flashed back to my own screening of Happy Gilmore 2 the night before, where members of the press gathered at a fancy hotel in New York City to watch it, and how I couldn’t stop thinking about how it was impossible to pinpoint when I’d seen the original film because it had probably been one I stumbled upon playing on TV while channel flipping with my dad. I bonded with other journalists about this bygone era of content consumption: How we, now entertainment reporters, used to watch so many movies in short bursts between commercials, censored by networks and abbreviated for time — never sitting down to watch something from beginning to end. We absorbed them through osmosis, which somehow made the jokes we caught even more memorable and quotable.

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I know my dad will watch Happy Gilmore 2 on Netflix at home in North Carolina without me and text me about it after, but I wish we could have seen it together in the living room of my childhood house, cackling together when Sandler yells something goofy or when the smack of his hockey stick against a golf ball results in a rocket-launch sound effect. The sequel’s touching father-daughter storyline would have added a sweetness to the raucous premise we initially bonded over.

“Ask if he ever considered having Bill Murray reprise his role as Carl from Caddyshack in Happy Gilmore,” my dad texted me when I told him I was interviewing Sandler. He gets it.

My dad is a big sports fan — a college track athlete and a longtime high school football coach. He’s always bonded with my brothers over sports, but I was lacking in the athleticism and attention span departments. Not wanting to miss any opportunity to hang out with him, I started playing a game with myself every time we watched a sporting event: I’d think of how rules could be added or subtracted to games to make them more fun. To watch a game closely enough to know exactly how to best break it is a twisted but profound love language.

Happy Gilmore put this into practice by treating a golf ball like a hockey puck. The fictional character knew that people should be able to smack it with as much ferocity as possible and maybe beat up a few haters on the sidelines, so long as they’re technically fine after. I applied this to my own thought experiments: Football players should have to hug the people they tackle afterward. If a hockey player gets put in the penalty box, they should be able to choose a song that plays for the length of their stay.

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While watching the sequel, I realized that having a guy come in and break all the rules of a sport and unexpectedly become the best at it is kind of a trend right now. There’s Happy Gilmore, of course, but Brad Pitt’s character does the same thing in F1, crashing into people constantly. I asked the Happy Gilmore 2 cast members to pitch other sports that would be fun to break the rules of for future movies.

Julie Bowen and Adam Sandler did interviews at Fiddler's Elbow Country Club in New Jersey. (Photo illustration: Yahoo News; illustrations; Jiaqi Wang for Yahoo News; photos: Kelsey Weekman/Yahoo News)

Bowen suggested Ping-Pong, and Sandler pointed out that Marty Supreme, a movie about table tennis legend Marty Reisman starring Timothée Chalamet, is out this year. (When I told him I can’t hear “Chalamet” in my head without saying it in the voice Sandler did at the 2025 Golden Globes, he kindly performed the soundbite for me.)

Safdie suggested basketball since it’s so popular — Space Jam and Air Bud pushed the sport to its limits, but there are plenty more rules to break. He directed The Smashing Machine, a mixed martial arts biopic starring Dwayne Johnson that’s out later this year and likely fits the bill, though he didn’t plug his upcoming project.

McDonald couldn’t think of a sport that needed to be broken in the moment, but he approached me after the interview to pitch that someone should ruin curling — maybe with a hockey stick? Not a bad idea for the next Happy Gilmore installment.

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“I love the fans. They just think the movie's the bomb,” McDonald told me. I saw it firsthand.

From the dudes rallying around Shooter McGavin to Sandler’s girl-dad tendencies to my own memories with my father that this whole experience brought up, it makes perfect sense to me why Happy Gilmore is a character that deserves revisiting. The nostalgia he inspires is tinged with warmth and community, uniting sports-loving fathers and pop culture-loving daughters as well as country club golfers and belligerent hockey players over a film about family, rule breaking and lighthearted physical violence.

Happy Gilmore forever.