Picture it: It’s a hot summer day. You’re shooting some hoops at a neighborhood basketball court. The sun is pounding down and the air is muggy, but you’re playing the best pickup game of your life. You’re dribbling your way to the basket, past some paltry defense, when suddenly a hand shoots out and blocks your way. You fumble; the ball is out of your hands. Your new opponent catches it, and you look up to see that it’s none other than Opera Man himself. Adam Sandler has joined the game.

Watch Adam Sandler Shoot Hoops On The Set of Hustle

It may sound absurd, but it’s a shockingly common story. Adam Sandler is a fixture in pickup basketball games throughout the country. His new movie, Hustle, in which he plays a rough-around-the-edges scout for the Philadelphia 76ers, is only the latest installment in a lifelong love affair with the sport. Below, we’ve traced a path through that history, from its earliest days to the Sandman’s role in Hustle.

1970–1980: Meet cute

“Basketball started for me [when] I was a young man,” Sandler tells Tudum. “I played with my dad, my brother and my uncle, who was 6-[feet]-6. And we had a telephone pole on our street... My father painted a little board brown, put it up on the telephone pole, put a rim on it. It was very small, so you didn’t have much backboard to work with. But we used to play hoops out there in the street, and when a car came by we’d have to stop. But I got addicted to it then.” Sandler went on to play church league basketball with his Jewish community center’s team. 

1980–1984: High school sweethearts 

While attending New Hampshire’s Manchester Central High School, Sandler joined the school’s basketball team, but by his own admission didn’t get much playing time. “I sat [on] the bench,” Sandler said on The Dan Patrick Show in 2019. “I was very slow, but I played guitar. My coach liked that, so he would have me jam during the basketball practices.” An auspicious beginning to a long career.

1990–1995: A hot Saturday Night date

During his five years on Saturday Night Live, Sandler’s love for basketball took a bit of a back seat, but he managed to sneak it into a few sketches. His Cajun Man “Weekend Update” character is mostly an excuse for a joyously undercooked Cajun accent, but it’s also a segment about... March Madness predictions? Of course, the pinnacle of Sandler’s basketball fandom on SNL has to be the week he worked with host and all-time greatest NBA star Michael Jordan. Unfortunately, Sandler didn’t snag an autograph — the cast’s demand for Jordan’s signature was actually slowing down rehearsals.

2000: Sympathy for the devil

In the satanic comedy Little Nicky, Sandler plays one of three sons of the Dark Lord himself. His character is a bit faster than the real Sandler at basketball. In one crucial scene, Nicky performs an outrageous half-court dunk on his brother, Cassius. Talented devil.

2005: On the rocks

The Longest Yard is by and large (long?) a football movie, but in an early sequence Sandler wins some cred after brutally losing to one of the prison’s hard-assed basketball players. In the process, he learns a valuable lesson that he probably should have learned from watching Rocky: It’s not whether you win or lose, but how you do it that counts.  

2010: Married life

Grown Ups might as well be a movie about Adam Sandler in an alternate universe: One in which he was a little better at high school basketball. The titular grown-ups are a crew of arrested-development cases who won their middle school basketball championship in 1978 and reunite after their coach dies. Unfortunately, their childhood rivals (including the great Tim Meadows) are just as immature as they are — they claim Lenny’s (Sandler) game-winning 1978 shot shouldn’t have counted. The film ends with a rematch and a lesson about the joy of playing with others. “What I loved about playing was hanging out, having teammates, wanting the same objective, wanting to score, wanting to play good D, comradeship from that,” Sandler tells Tudum. “Also, it’s guaranteed exercise for a guy like me who needs to possibly eat a little less.”

2013: Starstruck

Grown Ups 2 has far less basketball than the original, but it improves on its predecessor with the presence of Shaquille O’Neal, who plays the older brother of Meadows’ character. The film gave Sandler and company the opportunity to go on a delightful press tour with the towering NBA icon. And Sandler got some compliments along the way. “Adam is a damn good player,” O’Neal said when the cast joined Good Morning America. “No, no, really good. Good passer, good shooter, knows the game. And I think we’re undefeated.” Not bad for a guy who spent high school basketball practice playing guitar.

2019–2021: Pickup lines

The Sandler who regularly goes viral playing pickup basketball on Long Island courts has come a long way from his high school bench days. It’s not really that he’s blindingly fast — he’s efficient, a passing machine who’s not afraid to take a shot. He’s generous and helpful, but he’s also not in it for long-term glory. At one point in 2019, he made a basket, won the game and hit the road almost immediately. “He took his ball, dapped a couple dudes up, got in a really regular-looking car — that he street-parked — and just bounced,” Sandler teammate Chris Collins told MEL Magazine. “It was nuts.” Or, as his basketball-obsessed Uncut Gems character, Howard Ratner, might put it to former NBA star Kevin Garnett: “This is how I win.”

2022: Back to the bench

In Hustle, Sandler’s character asks Bo Cruz (Juancho Hernangómez) a simple question: “Do you love this game?” Sandler himself clearly does. “I lucked out getting into this movie,” he tells Tudum. “I love the sport. I liked being around gyms growing up. That’s all I ever did. I played pickup basketball literally five, six times a week, sometimes seven times a week.” As a 55-year-old man, he’s had to slow down a bit lately. “I’ve just been sitting back and watching hoop a little bit more than playing,” he says. Hopefully, he’ll be back.

Check Out The All-Star Roster In 'Hustle'Juancho Hernangómez, Anthony Edwards, Trae Young, Kyle Lowry, Jordan Clarkson, and Seth Curry are just a few of the prolific NBA players in 'Hustle.'