‘The Gentlemen’ and ‘Damsel' Star Ray Winstone Talks Us Through His Tough-Guy Filmography

Courtesy of Netflix

In the Netflix complicated-crime-in-great-clothing series The Gentlemen—the British director Guy Ritchie’s first foray into television, a reimagining of his 2019 movie of the same name—Ray Winstone plays a guy named Bobby Glass. This, naturally, results in a character saying, with no small fear in their eyes, “I respect Bobby Glass. Everyone respects Bobby Glass.”

Which is more or less the aura Winstone’s brought to most of the roles he’s played over the past 40-plus years—respect him, or else. The East London-born actor has made himself a minor legend embodying thugs, tough guys, hard men and other folks with whom you would not want to mess.

But in the heroic fantasy Damsel, the other Netflix property in which Winstone stars this month, Winstone plays against type as a king who must make a strategic marriage for his daughter (Millie Bobby Brown) without her entirely knowing what she’s signing up for. It’s a reminder that there’s more to him than the guy who can make other characters fold with nothing but a glare—although he's still very, very good at that. Here are 11 performances that display the full Winstone.

SCUM (1979)

Carlin, a young criminal

I got expelled from drama school the day I auditioned for Scum. I found myself going along with the rest of the guys who were at college who were going up for this job at the BBC Play for the Day for [the original 1977 production of Scum]. I was just going along for the ride, to have a beer with the boys. I started talking to the receptionist, and the receptionist asked me if I'd like to go in and meet the director, who was Alan Clarke. I was the last one in and we had a chat. Because I was the last there, he saw me out and watched me walk down the corridor. He said he employed me because he liked the way I walked; I was a boxer and walked like a boxer. It's nothing to do with acting, believe me. Getting expelled and getting Scum is this “sliding doors” moment for me.


Billy, a punk singer

The only way I was involved in music was listening to music. As kids, we had the plastic Beatle wigs with the guitars, and we used to sing outside like every other kid. But parties around my Mom and Dad's house when we were young, it was always Frank Sinatra and Tony Bennett, and everyone sang along. Punk was a whole different thing for me. When we came to do that film, I just couldn't get this thing of the way they dressed and all that stuff.

I remember my wife—when we were filming that in Vancouver, we'd only just got married, and she came along with me. I just couldn't relax into [the part.] I felt a bit of a fraud. And she said to me, “Well, you're not a singer. You're not. You're not a punk. You're not a rock and roller. She said, But you're an actor. You're supposed to act it.” I went, “Oh, right.” It took my wife, who had no idea of the industry, to actually put me in the place.


Will Scarlet, a not-so Merry Man

I’ve got to be honest—[at the time I got Will Scarlet] I wasn't that interested in being an actor. It just seemed a bit of a laugh to me at the time. People like me don't become actors. That's for other people. That's not for us. Basically, it was a series that paid the rent. “Oh, I'm going to earn a nice few quid here.” We just had Lois, our first daughter, and Jamie was on the way at a certain point during the shooting. It was a way of earning a living. It was a straight way. [laughs]


Raymond, a violent man

I met [Nil writer and director Gary Oldman] at Alan Clarke's funeral in 1990; we had a good chat there. He brought this script to the Royal Court [Theater], where I was doing a play. With scripts, sometimes you read them and you put them down and you pick them up again. This one, you don't put down. I've never seen writing like it.

We only rehearsed, I think, for a couple of weeks. Gary had one of these miniature movie cameras and he was just finding shots and playing with microphones so people could talk over one another. If he didn’t like something, he’d say [extremely Gary Oldman voice] “Raymond, I see you acting.” And I'd go, “All right, girl.”

It had a very British feel to it, yes, but filmed like Mean Streets, like an American film, which we were lacking in this country to a certain extent. It made me interested in being an actor. It made me feel that, yeah, I have a place in this profession.


Gary “Gal” Dove, a retired safecracker

I'm going to sound a bit poncy, but Gary's a lover. Sexy Beast, to me, is a love story. Gal’s not worried about the threat to him—he's worried about the threat to [his wife]. He wanted a different lifestyle. He wanted something else. But there’s this fear of this organization, this corporation of gangsters coming for you, that you got to say yes, because you got to protect her, you got to protect your friends.

And it was about working with [director] Johnny Glazer as well—it was his first motion picture. I mean, his eye is second to none. He's a proper filmmaker. But working with actors, it was new for him. He learned so quickly that a shot ain't working [if] the actor ain't comfortable. Let the actor do it first, and then put the camera where you want after.

Winstone (left, with Angela Bassett) in ‘Damsel’
Winstone (left, with Angela Bassett) in ‘Damsel’
Courtesy of Netflix


Bors, a knight

King Arthur was [directed by] Antoine Fuqua. I remember standing next to him in the field in Ireland and this helicopter came in and it landed. And this big fella with a great big cigar and a baseball cap got out. And Antoine went, “Fuck, man, who's that?” And I I went, “That's the money. It's got to be the money.

That job was fun. Mads [Mikkelson, who played Tristian] and all the boys. Clive Owen, who's one of the gentlemen of the film game, he's a lovely man. Ray Stevenson, God bless him, who's just passed away tragically. We had fun and we were a bit younger then.


Mr. French, a gangster

When I met Scorsese, I had this brown leather car coat on. A really nice one. Still have it. I went in to see him and we sat down and had a chat. I was supposed to play one of the cops, [but] I said, “I don't want to do a Martin Scorsese film playing a cop. I want to play Mr. French.” The only way you get to know about Jack [Nicholson’s] character, Costello, is through Mr. French. Their conversation, the way they are with one another. A few days later, I heard that I got the role. And Marty said to me, “Will you bring the brown leather coat? I wanted you to wear that in a film.” See, I'll get films on the way I walk or the coat I've got on. It's got nothing to do with the acting ability.


George "Mac" McHale, a British agent

A beautiful experience. It was just a wonderful thing watching Spielberg, and he loved showing you what he's doing. He’s not just a filmmaker, he’s a teacher as well. You understand the man you've got when you’ve got a teacher. You'll realize the camera's moving in a certain way in certain scenes and he'll show you that and he'll talk that through with you. I just loved it.


Dreykov, a Soviet baddie

I had a wonderful time making it, actually. I worked very closely with the director, and we created this awful character that is a groomer of young girls. Comic books are almost like old fairy stories: Don't go into the woods, what are these strange people about? I don't want to sound like being big-eared, but we were getting applauded, not just me, but the other actors applauded off set at night. Some of the best work I've ever done. Then I got a phone call when we'd finished telling me that we had to do some reshoots.

I just went, “I think you should get another actor, because I've just done it. I've done that and I was very happy with it.” But contracts are contracts. So I had to go back, but there was nowhere to go with the character. And in the end, they said it was fine, and you still had a nice time with people. But I felt that I was just a bad guy in a suit. I didn't feel that I'd contributed anything to it.

DAMSEL (2024)

The King

For me, it just rung out Sophie's Choice. You're the influencer. You're the head of your town, your folk, they tell him what the deed is and what's going to happen. And he has a decision to make, on the spur of the moment—his people or his daughter. And it's the decision he makes that destroys the man for one moment in time. Again, a sliding door. I think it's important that everyone brings something to the table when they come into a film. Not always accepted, and sometimes you're wrong, but that's why you have good directors. You sort that out.


Bobby Glass, a gangster

It was a long time coming, working with Guy. I love the fact that, again, it's about two families in a way. It's about the hierarchy, the mob up the top, who actually got all their property years and years ago for murder, rape, and pillage, and now have become the high society of our country. And then there are our families, which are the working classes who are trying to survive. The working class families and the aristocratic families. They need one another. It's a jungle out there.

Originally Appeared on GQ