This probably sounds unthinkable in 2024, but 25 years ago, the notion of Adam Sandler appearing in a film with even the slightest of awards hopes was considered deranged. The “Saturday Night Live” veteran was one of the biggest movie stars in Hollywood, but the movies that brought him to the mountaintop were almost all critically maligned goofs. Aside from the sweet-natured rom-com “The Wedding Singer,” Sandler was viewed as a juvenile vulgarian who unrepentantly aimed low. Even though he could procure the services of respected actors like Drew Barrymore, Steve Buscemi, and John Turturro, Sandler’s brand of inspired stupidity could not be accepted as worthy of their generation’s comedy imbecile Jerry Lewis.

So when word got out in 2001 that Paul Thomas Anderson, one of the most exciting young auteurs working at the turn of the millennium based on the strength of “Boogie Nights” and “Magnolia,” announced that he’d cast Adam Sandler as the star of his fourth feature which he’d written for the blockbuster goon, cinephiles of a certain age were aghast. Anderson had not only assembled a wildly prestigious cast for “Magnolia,” he’d landed arguably the biggest star in the world in Tom Cruise — who’d just worked with Stanley Kubrick. Now Anderson was going to work with Sandler? After he’d bombed out with “Little Nicky?”

Ironically, what felt like an affront to many film snobs was set in motion by the man who’d made his third movie a cinematic event.

How Adam Sandler Cruis-ed to Punch-Drunk Love

Adam Sandler dropped by the SmartLess podcast in 2020 and told hosts Jason Bateman, Will Arnett, and Sean Hayes that his path to working with Paul Thomas Anderson started when Nicole Kidman hosted “Saturday Night Live” in 1993. Kidman was married to Cruise at the time, so her husband tagged along to the show and found himself exchanging phone numbers with Sandler. Years later, when Anderson was shooting “Magnolia” with Cruise, he revealed to his star that he wanted to work with the clown prince of the multiplex.

According to Sandler, this is what happened next:

“Tom called me up, and he says, ‘I’m doing a movie with my friend Paul, and he’s a great director and he’s interested in doing a movie with you. Can I put him on the phone?’ Paul was very nice, and he’s going, ‘Hey, I loved “Billy Madison.”‘ And I was like, ‘Okay, thanks,’ but I didn’t know who he was. He goes, ‘I just love your movies and your albums. Is it ok if I write you a movie?’ I said, ‘You can do whatever you want man.’ He was sweet. I could tell he was funny.'”

“Punch-Drunk Love” received mostly enthusiastic reviews, but came up completely short at the Academy Awards. Anderson’s creative risk earned his film zero Oscar nominations, and while the movie turned a lot of snobs around on Sandler he has yet to receive an acting nod from the Academy (interestingly, Sandler was worried he’d ruin the film). That day, I am confident, will come. And as is often the case, it’ll probably be a make-up Oscar for this and “Uncut Gems.”