Lately, Kiefer Sutherland has been thinking a lot about regret and opportunity. The Canadian star has managed an impressive and varied career across iconic films (Stand by Me, A Few Good Men) and television series (24) over more than four decades, receiving plenty of awards recognition along the way. But for an actor who quickly became known for a kind of villainous mien—at least before his star-making 24 turning point—such a specific profile took its toll. “I wish I’d been a little smarter,” Sutherland says. “The thing I didn’t understand at 15 was that people take their movies really seriously and they take them really personally. I have had occasions where someone would not shake my hand because of a part that I played.”

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Arguably the worst offense came with the panned 1996 thriller An Eye for an Eye, in which Sutherland portrayed a psychopathic killer opposite Sally Field. He took the part because of the film’s Oscar-winning director, John Schlesinger. But Sutherland brings that film up on this week’s Little Gold Men (listen below) to reveal how the late William Friedkin cast Sutherland in his final film, The Caine Mutiny Court-Martial. Eye was developed by Friedkin’s widow and Paramount’s then chairman, Sherry Lansing. “Mr. Friedkin appreciated the fact that I was willing to take a role that was going to risk my entire career because I wanted to work with a director,” Sutherland says.

So Caine Mutiny, now streaming on Paramount+ With Showtime, feels like a full circle for Sutherland. Once again, it finds him portraying a dislikable figure—but in this case, it’s the richly shaded role of Captain Queeg originated by Humphrey Bogart in the 1954 film.

This latest cinematic take on the classic novel, which premiered at the Venice Film Festival less than a month after Friedkin’s death and is contending for this year’s Emmys, again takes the shape of a single-setting courtroom drama, in which Sutherland’s Queeg, captain of the USS Caine, spars with attorney Lieutenant Greenwald (Jason Clarke). Sutherland’s quivering, exacting take reveals a man battling both irrelevance and a changing world—and maybe a reckoning with his own failings. For Sutherland, the character hit profoundly close to home.

Vanity Fair: I saw this movie before it premiered in Venice last year, so it’s been a minute. I imagine it’s been even longer for you.

Kiefer Sutherland: It has, unfortunately. COVID and the writers strike, then the SAG strike, made the release of this film fragmented. I’m very excited for people to see it because, as much as I’m proud of my performance and I’m proud of all of the other actors, the story behind the making of this movie and the incredible talent that was on display was pretty extraordinary. We shot the film in two weeks, which is unheard of for a feature-length film. I’m in two parts of the movie and they’re split up by two different kinds of testimony that I provide in the course of the film. The second piece of testimony is somewhere between 20 and 30 minutes long. That was all done, from entrance to exit, in one take.

He had seven cameras moving at the same time in a very small space, which was that courtroom. To have seven cameras working like that in congress with each other is one of the most off-the-chart games of Tetris I’ve ever seen. And he did it with a kind of skill that was so matter-of-fact. We didn’t really even get full rehearsals because he knew what he wanted the cameras to do, and told each operator specifically what their requirement was.

To your point, this is a film that requires a certain level of finesse to keep it moving. How was this update of The Caine Mutiny presented to you? And how did you find your way in?

The fact that it was an iconic film to me—by virtue of Humphrey Bogart—and an iconic play, an iconic book, represented so many things that I was fascinated by. For my character specifically, two things collide together in the course of this film: It’s a man being confronted with who he is, not who he wants to be. That’s a terrible moment for anyone. That, I think, is heartbreaking, to come to the realization that you missed your own mark.

The other thing that I found so fascinating is this notion of becoming irrelevant. The US Navy was willing to put up with some of Commander Queeg’s misgivings because he was needed during a World War, and now he’s no longer needed. How do we get rid of him with the least fuss? As you get older, you are confronted with the world moving on. It’s not going to wait for you, and there is not going to be not even a day where the whole world mourns your passing…. As much as I don’t like some of Commander Queeg’s traits myself as a person, I have great empathy for what he’s going through. It’s also at a time in my life where, on some level, I’m questioning: How far off am I from the mark of the man that I wanted to be?

There’s certainly things I wish I had done better. You certainly can’t help as you get older to start to realize that there’s a lot of other young people coming up, and you are less relevant than you might’ve been 10 or 15 years ago. It’s very interesting to play a part about a series of topics that you’re actually dealing with.

You play some of those psychological disconnects in his physicality in a way I found very compelling. Was your preparation unique for this role?

Very much so. The preparation was just the volume of dialogue that was going to have to be learned as a play. Unlike a play, where you learn your dialogue and then you rehearse for six weeks and then you start performing it, that wasn’t going to be an option here. I knew that I had to work with someone so that by the time I went to shoot with Mr. Friedkin, I had a real strong sense of what I was going to do with it. As a director, he’s known for wanting the first one or two takes of a performance—and for very justified reasons.

When someone’s testifying and that much is at stake, they’re inherently going to be nervous, and they’re inherently going to be scared. That’s very similar to an actor performing a first take of anything, right? He wanted that natural kinetic energy to be going through you for real in the circumstances of your performance. It started like that. I worked with a woman named Beth Elliott and ran it top to bottom like a play, and the physicality started to find itself in places where I thought it was going to matter the most. The hands started to move. The foot kind of wedges itself into this uniquely uncomfortable position. All these little things telling you how tortured this person is, while the rest of the facade looks very presentable and cool and calm.

I revisited the film a little bit just before this, and you feel this sense of loss with William and with Lance Reddick, your costar, who also passed away recently. There’s a poignancy to it as well.

The poignancy is just the fleeting nature of it, right? You wouldn’t find a better-looking, stronger-looking man than Lance—you just won’t. And so that just doesn’t make sense. My heart breaks for his wife, for his family and friends, and you just have to take solace in what an amazing man he was and how many great things he did. But that’s never going to be enough, and certainly not for the people that surrounded him. And then William. [Pause] I think that’s the first time I’ve called him William.

That may be my fault.

No, no, no. I always called him Mr. Friedkin. I started off with “Sir,” and he kept saying, “You need to call me Billy.” And I said, “I can’t do that.” Then it ended up “Mr. Friedkin,” and I said, “Look, you have to understand, you’re the reason.” I was a theater actor in Toronto, Canada, and I was 15 years old, and I went and saw The French Connection. This was before VHS. This was the second, third run of the movie. I’d never seen a trailer for it. I just went to go see it because I’d heard it was something to see. And after that, that’s what I wanted to do. I wanted to tell stories like that, and I wanted to tell them like that. I wanted to tell them that violently, and I wanted to tell them that impactfully, in that current and that dynamic.

I’d love to go back a bit to what you were saying about how you connect to Queeg and this question of relevance, especially in the wake of some of your recent work. Something like They Cloned Tyrone is such a change of pace for you, or even playing FDR in The First Lady.

Well, Mr. Friedkin was a fan of 24, and I had done a film with his wife, Sherry Lansing, at Paramount called Eye for an Eye. Which was a really hard film for me to make, because the character was so awful. But I really appreciated the story, and John Schlesinger was the director, and I wanted to work with him. The one benefit of getting older is that some of the younger people that might be hiring you have no idea what you’ve done. [Laughs.] They’re willing to take a chance on you doing something different because they either don’t know any better, or they actually think you can do something different. When I look back, I wish I’d been a little smarter. *Stand by Me, The Lost Boys, Flatliners…*then when you start thinking of A Few Good Men, A Time to Kill, and all of the films that followed, and Eye for an Eye at the height of that, those were all characters that were just kind of nasty and not nice at all.

That’s true. You stood out, though.

My rationalization as an actor is, well, if those characters aren’t kind of awful, then the good part of this story can’t be told. Eye for an Eye was very hard that way. About a week after that had come out, my daughter was maybe eight years old, and we went to Chuck E. Cheese. I ordered a pizza. By the time we got to the table, all the other mothers had grabbed their kids and just left. Literally, we were the only people left in this restaurant that sat like a thousand people. My daughter thought I’d rented the place out for us. [Laughs] The character was just unfortunately just terrible.

It’s been hard, but in the earlier stages of a career, you’re always just so grateful to work. So being given other opportunities like They Cloned Tyrone—and the pandemic had something to do with it, I think. Less people were available. You take whatever opportunity you can. You do the best you can with it, and you’re grateful to have had it. I’m embracing the idea that with age comes opportunity and nuanced change.

When you’re a leading man, you’re holding the center a little bit more, whereas in something like Caine Mutiny, you come in and the energy is electric. You can be more unpredictable, right?

When you take a look at Anthony Hopkins in Silence of the Lambs, he’s barely in a quarter of it. But the impact he has is so great, and the performance that he gives is so profound, that he’s with you through the whole film. As an actor, you relish those kinds of opportunities. Jack Nicholson in A Few Good Men was a perfect example of that. I would say he was in less than a quarter of that movie, and yet commanded so much attention.

I know you just worked with another master, Clint Eastwood. Can you tell me about that experience and doing films like this in succession?

I had read that Clint Eastwood was making his last film. I knew that it had been predominantly cast, but I wrote him a letter introducing myself, telling him that one of the great dreams of my life would’ve been to have been in a film that he had made and that there was no part that would be too small. Like, “If it’s the greatest extra part of all time, I’m in. I would like to just be there. And I would like to say I was a part of it.” The part I ended up getting was not a big part, but it was a really impactful part for me when I read the script.

The first scene that I did was in a house. I’m introducing myself to another character and we’re becoming neighbor-friends. There was a tricky moment of how to navigate the last couple lines of the scene and then get out of the house. As I was leaving, I made enough room between myself, the camera, and the door, which was really narrow, and I only had a few inches on each side. I used a line to bridge what looked like an awkward way out. As I was starting to initiate that move, the first AD went to go say something, and I heard way off in the background, Clint Eastwood said, “No. Don’t. He knows what he’s doing.” And I got out the door.

I’ve had a really, incredibly fortunate career, but that’s a moment that’ll last with me forever. That for one brief moment, Clint Eastwood told his first AD of 25 years not to worry—that I would figure it out. And he didn’t fire me, so I figured I did.

This interview has been edited and condensed.