Since the age of 24, when he was hired as a writer on Saturday Night Live, Adam Sandler has not been what anyone would qualify as a loser— but he sure has felt comfortable playing one. From dimwitted hotel heir Billy Madison to Uncut Gems's luckless Howard Ratner, the prototypical Sandler character is a man incapable of making things easy on himself.

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Which makes Stanley Sugerman, the basketball character at the center of Hustle, in some ways yet another classic Sandler character. Burned out by the endless travel and long hours, Stanley dreams of becoming a coach but is shunted aside by his team's new co-owner, instead left to bet his entire future on a brand-new prospect from Spain, Bo Cruz (played by real NBA player Juancho Hernangomez). Stanley has a loving wife (Queen Latifah) and daughter (Jordan Hull), not to mention Dirk Nowitzki on speed dial, so he's better off than, say, Hubie of Hubie Halloween. But he's the kind of striving everyman Sandler perfected in The Wedding Singer or Punch Drunk Love, woven into a crowd-pleasing sports drama that has earned Sandler, fresh off the awards hype of Uncut Gems, a renewed wave of the best reviews of his career.

So, after 30 years as one of the most dominant forces in comedy, why does Sandler still feel so comfortable playing a downtrodden schmuck? "I just have a natural part of my brain that feels like I don't belong here," he says on this week's Little Gold Men podcast. "This feeling uncomfortable and loser stuff I've been doing for years, it's in me." But that unassuming attitude—like his casual fashion sense, a Sandler trademark—belies an incredibly busy schedule, with his Netflix movie deal, a stand-up tour, and a new project with the Safdie Brothers all on the horizon. For a guy who gets accused of just making movies in exotic locations with his friends, Sandler's schedule is remarkably busy and varied, and he seems to plan to continue surprising himself—and us. "If I feel a little like, I'm not sure how I'm gonna go after that, that's probably a good sign—[when I'm] nervous about a particular project."

Read below for excerpts from Sandler's Little Gold Men Interview, or listen to the conversation above. Topics include learning to write comedy on Zoom, how his father taught him to work a little less, and what he regrets about his past acting roles—but why he wouldn't change a thing, either.

I saw you in person at the last party I went to for a long time, at our Oscar party in 2020. You were there with the Safdies. I know the Uncut Gems process was a whirlwind, and I wonder how you felt the day after that. What did you feel ready for?

Boy, I just remember that whole process was fun. Getting to know those guys, getting to be with those guys, it kind of felt like the old days, like early Saturday Night Live, hanging out with a group, going places together, believing in a project together. I just felt like I had great teammates there.

Did that change what you wanted to do next?

I think that it always goes like that. Whatever you're feeling in the moment, you enjoy that moment. And then you say, "What can I do to..." I mean, it doesn't happen every time, but you say, what can I do, what feels right next? What would I think is gonna be exciting for me? What might be interesting to the audience? You try to mix things up and do stuff that makes you wake up and go, "Oh man, I gotta go crush this."

So then a month after that Oscar party, COVID hits. Then what do you decide you wanna do?

That was all, like everyone else on the planet, just making sure the family was safe and everybody was good. And then eventually as it progressed, time was moving on and people were finding ways to work. I remember the movie Hustle, I think that came up, and then I met Jeremiah Zagar, the director. We met because Ted Sarandos from Netflix told me I should watch his movie. And I watched this movie We the Animals and I loved it. And I called him up to just tell him how much I loved it, and we were discussing stuff and somehow we ended up talking about this Hustle movie. We started Zooming and jamming on stuff over Zoom every day.

I think you said that Hustle came to you from LeBron James's company. So had you been talking to them before? Had you been trying to pursue something with his company before this one came up?

This all, like most of the stuff I've been involved with, just luck. Joe Roth, who also worked on the movie and was partners with LeBron on this movie, they somehow thought of me and they sent it my way. I loved it immediately. I loved the idea of behind the scenes basketball and getting to see hard work. And I'm just a big fan of so many players and basketball has been such a huge part of my life, so it was exciting.

Had a basketball movie been on your mind before that came in? You're such a big fan. 

Yeah, yeah. You know, I've involved basketball over the years in my comedies and stuff, but this was a different approach at it. Like when I did Uncut Gems and I was [playing] a jeweler, I was starting from scratch because I knew nothing about jewelry. So I had to do a lot of preparation and being comfortable and confident in knowing as much as I could know about the craft and that business. Basketball I had a nice head start because I knew a lot of stories, a lot of stuff. I knew a lot of players over the years. I knew my history—not as much as, like, a super fan, but I'm pretty in there.

I was thinking about Stanley Sugerman in the line of losers that you've played on screen, because they go back a long way. And you had success pretty early in your career. I wonder if it's just that playing losers is fun, or if there's some kind of sliding doors— like, "that could have been me"—to those characters that appeals to you?

That's a good question. I think I'm comfortable in that world. It's probably natural to me, because I don't... I've been doing this a long time. I mean I just went on stage last night. When I first walked on the stage, I never go like, "All right, here I am." I'm always just like, "Oh, oh, oh, what the hell am I doing here right now?" I just have a natural part of my brain that feels like—I don't belong here, why am I setting myself up like this, I don't think I should be asking people to look at me right now. So I guess it's this feeling uncomfortable and loser kind stuff I've been doing for years, it's in me.

Do you get to the end of the day and just think, okay, thank god I can go back to being with my family and in my own life? Do you get all that out on the set?

I like being on a movie set. I'm probably the most comfortable on a set—

More than on stage?

Stage, if it's rolling along and we're doing good, I feel great. In standup you could be killing for 15 minutes and then all of a sudden make a wrong turn and then the last 10 minutes of the show it's like, "Wow, what happened there?" You got to concentrate, you got to just ride it out, feel comfortable. Sometimes you veer off and all of a sudden you lose the audience, and sometimes you lock into getting them back and then sometimes you walk of stage going, "Wow, that hurt. That was a painful moment for everybody."

Is that part of what brings you back, when you're like, "Okay, well that didn't go right, but I can do it better next time."

The nights you do poorly you cannot wait to get introduced again somewhere else to make up for it, because you're like, "I can't live with that one. Let's end on a good one." And then when you have a super show part of your brain is like, "Yeah, why am I doing tomorrow night, man? There's no way the show is going to go as good as that." There's no way you can crush it perfectly. It's just some nights where just your energy is great, the audience's energy is great. It just connects and then you go, "Let me try to duplicate that," and then that just never works out for you.

I think it's interesting when people are in the position in Hollywood to be able to choose what they do, because as you know, not a lot of people get to do that. So when someone comes you with a script or someone to work with, what kind of makes you say, "Oh yeah, that's the thing"?

Who's involved with it, if I can act to a subject matter. If I feel a little like I'm not sure how I'm going to go after that, that's probably a good sign—that nervous about the particular project. I'm going to do a movie with the Safdie brothers and we're supposed to start in the late winter, right. So part of my brain right now is like, "I'm on tour." Then once that Safdie brothers movie starts—and I love those guys, I know we're going to dedicate ourselves into working our asses off and making sure it's as good as it can be, and I know that takes a lot of time. So part of my brain is going, "Wow, once that movie starts I'm in deep and our lives are going to change." Like everybody, when you work hard you're tired, you're knocked out, and you miss out on some stuff that you wish you could've seen. But ultimately, I know it's going to be a few months of going after a goal that we all feel the same about. We want to do the best we can.

So you expect that to be as intense as making Uncut Gems?

Yeah, because of how much these guys care. And how much I don't want to let them down. And I see how hard they work, and just like when I'm working on my comedies with my friends, it means a lot to us. Every joke means a lot. The Safdie boys, every word means a lot to them, every frame of the movie means a lot. So I don't want to walk through anything. I care about it, and I respect those guys so much.

When you look back on your comedy or even your acting, like before Billy Madison, do you recognize that actor and that person? Do you still feel like you're that same person or do you feel the distance there?

I feel the same in the way that I was always pretty excited to be doing it. I don't look back at any of my old stuff and go, "Wow, you nailed it there, man." I'm usually like, "Wow, you were just getting by, man." I think just getting more and more settled as a human being, my acting is probably changing over the years. I always thought I was doing the right thing in the moment, and I still do, but I look back at even stuff from five years ago and I go, "Oh, should've done this, man, that was a little weird choice that you made there, man. What the hell happened?" Maybe I played it too big or maybe I played it—I was too trying to show what I was feeling in that moment or the joke was over the top or whatever the hell it was. But it meant a lot to me and I believed in it then, so I still back it up.