Adam Sandler’s Everlasting Shtick

We cruised down West Pico in Adam Sandler’s ride, a custom Chevy passenger van tricked out in the style of an orthopedic shoe. The cup holders jangled with suburban odds and ends — a pair of tiny glasses belonging to his daughter; a bottle of Dry-n-Clear ear drops. We were bound for Hillcrest Country Club, the oldest Jewish country club in Los Angeles. “You’re going to like this,” Sandler said. He whipped the van into the valet station. Alongside the row of town cars and coupes, it looked like an airport courtesy shuttle.

Hillcrest was founded in 1920, when Los Angeles’s Reform Jews started earning major cash and no country club appeared willing to let them spend it. Barred from joining the WASP establishment, they banded together to forge a simulacrum, a place where self-proclaimed “Jewish big shots” could unwind in semiassimilated fashion. Today Hillcrest is an upgraded Eden with 18 holes, a pool, tennis courts and an initiation fee of more than $200,000. The club’s dress code, a three-page document, betrays the legislative eagerness of a people only recently allowed to make the rules: Hat bills must face forward at all times; jeans will be worn only in the Men’s and Ladies’ Card Rooms. That day, Sandler was wearing cheap surf-shop shades, untied and toe-creased Jordans and capri-length silky basketball shorts. He vetted the outfit before the hostess’s stand.

“Hey, am I too disgusting?” he asked.

“You’re always welcome here,” the maître d’ replied.

Sandler stepped inside to consider the buffet, then quickly refocused himself on our mission. He’d taken us there to look at old photos of a group of Jewish comics called the Hillcrest Round Table, who met for a standing lunch throughout the 1940s, ’50s and ’60s. This overt gesture toward comedic lineage, done for a reporter’s benefit, was exactly the kind of stunt that Sandler had avoided for years. He last sat for a magazine profile in 1996, not long after his comic ur-text, “Billy Madison,” came out.

I started chasing Sandler in early 2017. His presence in my own childhood had been mythic — a Jewish cultural influence more imposing than anyone I’d ever learned about in Hebrew school. Thinking about the scope of his career, I was enchanted by the prospect of me, a person of modern and hardly coherent gender, grappling with America’s foremost man-child. I dispatched my editor to email his publicist. At night, from my apartment in Queens, I wondered if Sandman, from his mansion in the Pacific Palisades, was considering my offer.

We followed up. Time was marked by the arrival and deletion of my weekly “Adam Sandler” Google Alert, which detailed a still-persistent comedy career, achieved with infrequent engagement with the press. Soon he mocked me everywhere I went, his face staring down from the subway ads for his latest movie, “Sandy Wexler.” On Netflix, his new stand-up special debuted, and he did the late-night shows. I waited. Months turned to years. And just like that, the Google Alert started to spit out photos from a movie set: Sandler in a louche leather coat and diamond earrings, filming the indie thriller “Uncut Gems.”

Sandler had taken dramatic roles before, most notably in Paul Thomas Anderson’s 2002 film, “Punch-Drunk Love.” Then, as now, a question emerged: If he was such a good actor — and he was — then why did he keep making dumb comedies? This was a question I had long since learned that he resented, and in my pursuit, I had been careful to avoid it. Now it seemed the precaution had paid off. By some act of God — or, more likely, behind-the-scenes arm-twisting — we found ourselves together at last, standing in his country club, staring down the gallery of early Hillcrest members.