Movies For Grownups Career Achievement Award Winner Adam Sandler Keeps Defying Expectations — Even His Own

The Gen X icon admits he never expected to receive such an honor. “I was always trying to just continue marching forward,” Sandler says. “But it’s random moments like this that are interesting. It’s almost like flipping [on] the TV and seeing an old movie of yours. You just go, ‘Oh man, I used to be pretty damn skinny!’ ”

There is no shortage of films that still make that broadcast rotation. After his five-year stint on Saturday Night Live from 1990 to 1995, Sandler embarked on a successful run in films including Billy Madison, Happy Gilmore, The Wedding Singer and The Waterboy. While those films didn’t receive critical raves, they were financially successful and became instant comedy classics, and in 1999 Sandler founded the production company Happy Madison that specialized in the broad, goofy comedies that made Sandler a household name. 

In 2002, however, Sandler changed direction and appeared in his first “serious” film role with Punch-Drunk Love from writer-director Paul Thomas Anderson, 55. His performance earned him a Golden Globe nomination for best actor and proved his dramatic acting chops, even if the film — in which Sandler starred as a socially anxious businessman who falls in love — is certainly a comedy, albeit darker and more grounded than his earlier fare.

Since then, he’s seamlessly alternated between those two poles. Among the numerous comedies like 50 First Dates, Anger Management, and You Don’t Mess with the Zohan in his filmography are sober turns in Reign Over Me (in which Sandler played a man struggling with depression following September 11), Men, Women and Children (an ensemble drama about troubled relationships), and Uncut Gems (a crime thriller for which Sandler won the 2020 Movies for Grownups Award for Best Actor). 

“There’s a difference between the [movies] I make with my buddies and something like Noah’s movie,” Sandler says of Jay Kelly, his second collaboration after The Meyerowitz Stories with director Noah Baumbach, 56. Since he’s only on board as an actor and not a producer, Sandler respects his role as a member of the larger team. “It’s Noah’s movie. He writes it, puts it together, shoots it, decides what’s right. I just try to do the best I can for him and don’t let him down.”

Baumbach, who cowrote the film with 54-year-old British actor Emily Mortimer (who also plays Jay Kelly’s makeup artist), envisioned the role with his friend Sandler in mind, and revealed as much years ago before the official offer came to the star. “You just get excited,” Sandler says of first hearing of Baumbach’s idea. “I don’t know when that’s coming, but that will be fun. He writes pretty on-the-money stuff that happens to be funny as hell and smart as hell, and can also break your heart. It’s beautiful.”

One can see the similarities between Sandler and his character pretty easily. Ron is affable and kind, alternating between doing everything he can for his client and friend and keeping his family happy. The latter is what Sandler really related to the most, particularly a scene toward the end of the film in which Ron reads a book to his son over FaceTime as they’re on opposite parts of the world. “That just feels very real,” Sandler says. “When [I’m] making a movie, most of the time my family is with me. But when they’re not, I’m just dying to get any time with them on the phone … and let them know I’m thinking of them. And they let me know they’re thinking of me.”

Jackie Sandler and Adam Sandler attend AARP's 19th Annual Movies For Grownups Awards in 2020.

Getty Images for AARP

It’s the relationship between Jay and Ron that is the film’s central conflict, with the spoiled and self-centered actor unable to give back to his devoted manager. Their friendship is also complicated by the transactional nature of the actor-manager partnership: Is Ron a real friend, or just another one of Jay’s many employees? It’s a complicated situation that Sandler knows well as a Hollywood veteran. 

“It feels like a lot of relationships in our town — and also [with] every job,” says Sandler. “You see each other daily, and you have some sort of closeness and rapport. [Jay and Ron have] been through so much together, and they do feel a true affection and love for each other.” He has seen this relationship play out among his peers over the years, and it was very real in the film that Jay and Ron are tempted to go their separate ways. “I've heard a lot of different people say, ‘Oh, I have a new agent,’ and that is part of the business, too — starting new relationships,” the actor says. 

But Sandler himself doesn’t relate, as he’s tried his best to maintain a community of friends and collaborators in his orbit. “I've had the same team for a very long time, since [I was] a young guy, and I see they feel very close to what I’ve done and the choices I’ve made,” he says. “They’re a part of those decisions and thoughts, so it feels like [everyone feels] the ups and downs together.”