Ray wears tux by Connolly, vest by Marks and Spencer, chain by Goosens, glasses by Jacques Marie Mage // 📸 : Gavin Bond

The Legendary Ray Winstone on Life, Love, and Loyalty

"Walls are there to be knocked down," says Ray Winstone, as he reflects on his journey from London's war-ravaged East East to his current perch at the top of the Netflix global TV show and movie charts, with The Gentlemen and Damsel respectively.

Words by John Pearson
Photography by Gavin Bond

If, like me, you’re Gen X, then you’ll remember key moments from our cultural landscape. The day Elvis Presley died, hearing that Marvin Gaye passed, the moment you were told that John Lennon had been shot in New York City. You also might remember the thrill of the school corridor when your pubescent classmates were lit up by the gore of having seen Ray Winstone’s character Carlin pack a sock with snooker balls and give a vicious beating to his nemesis in legendary director Alan Clarke’s brutal and uncompromising 1979 film Scum. “I’m the daddy now,” he growled. Which he certainly was, and remains today.

That, and films like Quadrophenia and That Summer, were the genesis to a career that hasn’t ceased in momentum and has rightfully placed Winstone on the mantle of greatest British actors of all time.

Ray wears Coat Vintage, Suit shirt by Tailour Tie vintage // 📸 : Gavin Bond
Ray wears vintage coat, suit and shirt by Taillour, vintage tie // 📸 : Gavin Bond

Winstone, born and bred in post-war London’s battered East End, was beloved by his parents and inspired by England’s World Cup winning captain, Sir Bobby Moore, a man who shared similar humble beginnings, who was local to his manor, and led his beloved West Ham F.C. — a gentleman who epitomized what could be achieved.

Influenced in the movies by the likes of John Wayne, James Cagney and Edward G. Robinson, at the age of 12 Winstone stepped into the world of pugilism as a welterweight, collecting 80 trophies, winning three London schoolboy titles and fighting twice for his country. He really was, and is, hard as nails! With a film, TV, and theater resume which reads like a who’s who of creative giants, Winstone has worked with Martin Scorsese (The Departed), Steven Spielberg (Indiana Jones), and Anthony Minghella (Cold Mountain) on big-ticket Hollywood films, whilst also committing to debut directorial movies by his peers, Gary Oldman (Nil by Mouth) and Tim Roth (The War Zone). He’s shared the screen with the likes of Michael Caine, Tom Courtney, Michael Gambon, Anthony Hopkins, Sir Ben Kingsley, Russell Crowe, John Hurt, Mel Gibson, and Harrison Ford. That’s decent company to be keeping.

Ray wears Cahmere sweater by Connoly // 📸 : Gavin Bond
Ray wears cashmere sweater by Connolly // 📸 : Gavin Bond

Speaking the other day with a lady friend of a vintage age, around 25 years my senior, she immediately glowed with delight when I mentioned that I’d interviewed Ray and said that Sexy Beast remains her go-to movie when she wishes to be truly entertained. “I like to imagine the fun they had with each other in between takes,” she said. Winstone does that to us, he touches that chord, and seamlessly crosses the generations. As renowned film critic, the late Roger Ebert, said of Winstone’s presence in The Departed, “He invests every line with the authority of God dictating to Moses.”

And so it was, when 15 minutes after wrapping our Mr Feelgood shoot in London, our photographer, Gavin Bond, a seasoned veteran of fashion and A-list subjects, called me to say that, “I think I’ve just had the very best few hours of my professional career working with Ray.” I received an email from Greg Chapman, our stylist on the shoot, later that night expressing just the same. When I informed Ray of this, he was quick to respond, “Please tell them ‘thank you’ from me. God bless them, we had fun! You’ve gotta have a bit of fun, you know? It was very enjoyable, and you know, if you’re not a male model and you’re getting your picture taken — it’s not my game. But just to have a great group of guys, it was blinding.”

Ray wears Tux by Connoly, Vest by Marks and Spencer, Chain by Goosens, Glasses by Jaques Marie Mage // 📸 : Gavin Bond
Ray wears tux by Connolly, vest by Marks and Spencer, chain by Goossens, glasses by Jaques Marie Mage // 📸 : Gavin Bond

Showing no sign of slowing down, and now playing drug baron Bobby Glass in Guy Ritchie’s The Gentlemen — currently the streamer’s No1 show in the US, UK, and worldwide — Ray, 67, says, “You’ve got to keep working. We’re not in the business that we can stop working and retire, because you can’t be a year behind in your tax. They’ve kind of got you by the short and curlies. It would be lovely to be able to come back and do a job now and then when you feel like it. But I’m kind of a workaholic. I’ve tried not working but it doesn’t work for me. I get itchy fingers because I want to be doing something. So I think for me, I’ll keep working until I can’t.”

This month has also seen the Netflix release of Damsel — currently the streamer’s No1 movie in the US, UK, and worldwide — written by Dan Mazeau, and directed by Oscar-nominated filmmaker Juan Carlos Fresnadillo. Winstone plays the king to Millie Bobby Brown’s princess, whose Prince Charming flips the script and sacrifices her to the dragon. Also sharing the screen are Angela Bassett, Robin Wright, and Nick Robinson.

As a father of three daughters and with a marriage that’s lasted over four decades, you get the sense that family means everything to Winstone. It’s his bedrock. And he had this to say about speaking to one of his daughters about her following in his footsteps, “If you’re lucky enough to do the thing you love doing, and you have a chance of doing it well… There’s a million people out there who do jobs they can’t stand doing. If you don’t try, if you don’t have a go at it, then you’ll never know — and you’ll regret it the rest of your life. So if you enjoy what you do, then you’re in the best job you can ever have.”

Ray wears Sheepskin Jacket by Connoly, Glasses by Jacques Marie Mage // 📸 : Gavin Bond
Ray wears sheepskin jacket by Connolly, glasses by Jacques Marie Mage // 📸 : Gavin Bond

And reflecting on other aspects of his long and journeyed career, he adds some sage advice, “Rejections make you stronger and if they don’t, then you’re in trouble. You have to dig in, you have to, you have to have another go. And so I look back and I’m quite proud of that. That I kept on through the rejection, through everything else, and just thought, you know what, I might be a little bit different, I’ve got different ideas, I’ve got a different way of going about work, sometimes rightly, sometimes wrongly. But I can look back with pride and say, ‘Yeah, I’m very proud of that, and I’ve had a great life.'”

It was an absolute pleasure speaking with Winstone, an integral player in the cultural fabric of our lives. He was as polite, open, warm, and affable in stark contrast to the villains he’s portrayed over the years. We hope you enjoy the photographs (he made a fantastic male model!) and our conversation in our latest installment of Mr Feelgood’s ‘Who the F** Are You?’ profile, answering the 20 questions that get to the heart of who we are.

Who the f*** are you?

Well, I’m Ray Winstone. I’m 67 years of age.

Ray wears Coat Scarf and Trousers by Connoly, Boots by Grenson // 📸 : Gavin Bond
Ray wears coat, scarf and trousers by Connolly, boots by Grenson // 📸 : Gavin Bond

How are you feeling right now?

At the moment, at this present time, I’m feeling pretty damn good! I gave up smoking a year ago and I was sitting in my car and I fancied a cigarette. I dunno why I fancied a cigarette, I’ve never really liked smoking, it’s something to do with your hands I guess. So I bought a packet of cigarettes. I was in the car and I lit it up and I took a puff and I just thought, what the f*** am I doing? I wanna see my grandchildren grow up. So I just threw it out of the window. I know I was littering and that’s a bad vibe but I just screwed up the packet and threw it away, and I haven’t had a cigarette since. I found it pretty easy, you know. I have a bit of a vape, every now and then. The thing with me and cigarettes is that I never really took it down. It was just something to do, I guess. It’s funny the way your life changes. You get to a certain age and you think about your own mortality and I just fancied a clean-up. The detox in the morning [from smoking] is worse than you get from a hangover. I haven’t had a drink in nine days. In Covid, I really caned it. There was nothing else to do. I got right on it during Covid and I found that I was having a drink more or less every night. And I thought, what am I doing? I’ve gotta get out, I’ve got to motivate myself a bit. And now I feel great, I feel absolutely blinding. I didn’t have a drink on my birthday [two days prior to our interview] and I’ve gotta say, it’s very good for me. I didn’t want it, and I was working the next day anyways. It’s funny, I make my mind up to do something and I do it. I’ve got that kind of mentality. I’m a lucky boy there, you know.

Ray wears Hat by Herbert Johnson, Coat and Scarf by Connoly // 📸 : Gavin Bond
Ray wears hat by Herbert Johnson, coat and scarf by Connolly // 📸 : Gavin Bond

Where did you grow up and what was it like?

I was born in Hackney hospital, in 1957. Brought up in Plaistow, West Ham, E15 — went to the Brimsdown school. It was a bomb site, 12 years after the Second World War. And whilst they were rebuilding Berlin and Munich and all them gaffs, London was still a bomb site, you know. And that’s where we used to play. They were great memories, all the summers seemed longer then — hotter and longer. I don’t know why. Perhaps because when you’re kids, time goes slower. It was a really joyous time. Everybody in the street knew everyone. Everyone looked after one another’s kids. Whenever there was a party, everyone from the street was there. It was like a family. I hold great memories of the place.

What excites you?

Wow! West Ham winning the European Cup, that excites me. I know everyone probably says this and quite rightly so, but watching my kids grow up. There’s not another answer because there’s nothing more than family. Watching them grow and develop from these little things, and growing into women and then producing you a grandchild, a son. I had three daughters and now I’ve got a little boy in the firm. And that, that excites me. It drives me crazy as well but it excites me at the same time. If you wanna talk about work , then yes, walking onto a set that you’re really happy with, with a good script and good people, that can excite you. It don’t happen that often but when it does happen, it’s good.

Ray wears Suit Shirt by Tailour, Tie vintage, Glasses by Jacques Marie Mage // 📸 : Gavin Bond
Ray wears suit and shirt by Taillour, vintage tie, glasses by Jacques Marie Mage // 📸 : Gavin Bond

What scares you?

Oh, I don’t know. The way the world is, I guess. You look at it all. The Russian/Ukraine conflict. There’s been so many good documentaries lately. I watched one on [Alexei] Navalny the other night, who they just found murdered. What is going on with human beings? Where does it come from that we just completely destroy one another? All the time. And it’s all about land. About having something that’s not yours — it’s about gangsterism really, taking something that’s not yours. And everyone blames everyone. Well, our generation, we’re on our way but the next generation, they’re completely f***ed. And it’s not getting better, it’s getting worse. Freedom of speech has gone out of the window. That’s what frightens me, you know. It ain’t so much for me, it’s for my kids and their kids and theirs. How long are we going to be around for? Because the way it’s going, we’re not going to be around for much longer. And do you know what, quite rightly so.

Ray wears Leather Jacket and Cashmere sweater by Connoly // 📸 : Gavin Bond
Ray wears leather jacket and cashmere sweater by Connolly // 📸 : Gavin Bond

What’s your proudest achievement?

Again, a bit of a cliché I guess but again, having my kids, having a family, being married for 44 years. God help us, ask anyone who knew me 45 years ago if I’d be married to the same woman, it would have probably been a no. I was a bit of a handful, you know. Actually, becoming who I am now to what I was. Because without that, I wouldn’t have what I’ve got today. So yes, I’m proudest of that.

What’s the hardest thing you’ve ever done?

Honestly, that question’s really a double-edged sword because it’s probably walking into a boxing ring for the first time, or walking onto a film set. Not just the first time, but the first few times. Kind of believing that you’re not really supposed to be there, and having to get over that. I think the boxing ring got me ready for it. You can get punched on the nose, or laugh it off if you do it wrong, but sometimes I’d rather be punched on the nose. But walking onto a set didn’t take that long to get used to because film sets are really quite down-to-earth. Theatre was a little bit different because that can be ‘them and us,’ and I’ve felt that in my own inverted snobbery in a way. So it was something I had to get over, more than them. There are probably plenty of actors out there that don’t think I’m much of an actor, and that’s fine, you know. We all have opinions about people, and that wasn’t really my worry. I guess my problem was with me, that I didn’t quite believe that I was in the profession where I was supposed to be.

Ray wears Sweater by Connoly, Eye rings by The Great Frog // 📸 : Gavin Bond
Ray wears sweater by Connolly, eye rings by The Great Frog // 📸 : Gavin Bond

Who was your greatest mentor and what did they teach you?

There’s a few there. From being a young boy, watching Bobby Moore. Because of where we came from, and this is crazy, but the heroes were gangsters — Reggie and Ronnie Kray and all that. It’s all people ever talked about. And then Bobby Moore came along and became captain of England. And he came from our manor, he came from up the road. And he presented himself as a gentleman, he wiped his hands when he shook hands with the Queen. He was kind of the first. Then obviously my father. And my grandfather ‘Toffee’ — Charles Thomas Winstone. I lived with him for a while and he was an absolute gentleman. He used to wear a suit and raise his hat to ladies. It was that time. And before I went to work, I went to a boxing club called the Repton Amateur Boxing Club. And we had a trainer there called Tony Burns. There’s many of these guys around at amateur boxing clubs now, and it’s not just about the boxing, about being a champion, it’s about taking kids off the streets and turning them into men. And that’s not through the physical side of it, it’s through the mental side. To have respect for your opponent, to have respect for people from all walks of life. So that kind of made me ready for the world. And then you’ve got people like the director Alan Clarke who was a mentor to me as a teacher. Ian Rickson at the Royal Court Theatre. There are probably one or two more along the way, but those come to mind now.

Ray wears vintage coat, suit and shirt by Taillour, vintage tie // 📸 : Gavin Bond

Who are your fictional and real-life heroes?

Fictional heroes? I don’t think I’ve got any, not that I can think of at the moment.

Again [in real life], Bobby Moore — an absolute hero. We went through a stage in the 60s when we didn’t like [Muhammad] Ali because he messed up Henry Cooper. You know he cheated in that fight, they cut his gloves and all that. But over the years when you find out about the world and what he stood for, then he becomes a hero. I actually love Smokin’ Joe Frazier. He was so game, he’d get knocked down and then he’d get back up. Rocky Marciano, I’ve seen all his fights from back in the 50s. What a man he was. And I have to say John H Stacey. John H Stacey came from my club. He was older than me. He won the world championship in Mexico again José Nápoles. He went there with no chance and won the world title and for us kids, coming from our area, it meant everything. There was nothing you couldn’t achieve. So I’ve got to say that John H Stacey is a great influence in my life. Walls are there to be knocked down. You’ve got to knock the walls down, you know.

Ray wears Cashmere sweater by Connoly // 📸 : Gavin Bond
Ray wears cashmere sweater by Connolly // 📸 : Gavin Bond

What is your favorite item of clothing in your wardrobe?

I do like my spectacles. I have to wear slightly dark glasses to look at the videos. You know the blue screen — it starts to do your eyes in. I love spectacles, I spend money on spectacles because I think they’re important. Shoes. If you have a bad suit on with good shoes, the suit looks good. I think at the moment my favorite thing in my wardrobe is the suit I wore at my daughter’s wedding. It’s by Gresham Blake who’s based in Brighton but he’s also in the City of London and the West End. We based my suit on an Elvis suit because my daughter’s an Elvis fan. She loves Elvis, as we all do. So I kind of modernized the style — it’s a light purple mohair! It’s tricky, it’s a bit tricky, I gotta tell ya, but it’s my favorite item of the moment.

Ray wears Tux by Connoly, Vest by Marks and Spencer, Chain by Goosens, Glasses by Jaques Marie Mage // 📸 : Gavin Bond
Ray wears tux by Connolly, vest by Marks and Spencer, chain by Goossens, Glasses by Jaques Marie Mage // 📸 : Gavin Bond

What music did you love aged 13, and do you still love it now?

The Beatles, I was probably about six or seven when the Beatles started kicking on. That kind of pop. And the Rolling Stones who were probably going through that psychedelic phase at the time. They got a bit weird for us because we were a bit mod. It was a bit of that, and then we built up to Motown. And then I remember reggae coming coming in, that was great stuff. And then it was The Clash and the Sex Pistols. So it was a great time in Britain, in England, we were the guv’nors, putting all that stuff out all over the world. But I also grew up listening to Frank Sinatra, Tony Bennett and Judy Garland. Every Sunday morning Dad would go out and get the papers and the bread and come back, and we’d read the papers in bed. We used to have a record player in the corner so we’d all get on the bed and listen to Frank Sinatra — and we still listen to Sinatra.

What is the most inspiring book you have ever read?

Do you know what? I’m not a great reader of books. I couldn’t really read properly until I was 11 and I probably was a little bit dyslexic and didn’t know it. But then I started reading scripts, and scripts I read more than anything now. The one book that I did read that I can tell you about, a book I loved, was The Searchers. You know the John Wayne film, The Searchers, one of the best western’s ever made? I had the book and it had very small chapters, so at night when you’re chilling, just before you go to sleep, you can read a chapter. It’s an amazing book because you can literally smell the prairie when you’re reading it. And because I’d seen the film, it was so good, I could picture it. Although years ago we read Paddington and Lord of the Rings — actually the teacher read Lord of the Rings to us, so I’d be cheating if I said that one!

Ray wears Coat by Applied Art Forms, Glasses by Jacques Marie Mage // 📸 : Gavin Bond
Ray wears coat by Applied Art Forms, glasses by Jacques Marie Mage // 📸 : Gavin Bond

What is a movie that has left a lasting impression on you?

There’s a few. There’s many films that I love. Once Upon a Time in America is one of my favorite films of all time. There’s a film called They Shoot Horses, Don’t They? It’s probably the most boring film you’ll ever watch for 90% of the film. And seeing it kind of ruined things for me, because I have to read the script to the end now, in case it gets good. It starts off with a horse running through a field with a kid chasing it. The horse falls and breaks its leg, and you hear the gun go off. It then cuts to America during the depression and there’s a marathon dance competition going on at the end of a pier, and it’s Michael Sarrazin and Jane Fonda. They meet at this competition and they have a dance. And the dance goes on and it’s f***ing boring. I mean the director, Sydney Pollack was so brave to make this film, the way he made it, because I’m going, “Come on let’s have something, let’s do this.” You get involved in their lives but you still need something to happen. They don’t even win the dance competition. They get disqualified, or something like that. And then they’re standing there at the end, and they’re talking, and she pulls a gun out and gives it to him. She says “kill me” and he goes bang and he shoots her in the head. And you think, f***, what happened there? They put him in a paddy wagon and the cop says to him, “Why’d you do that son?” And he says, “Well, they shoot horses don’t they?” And your hair stands up on your head. You’ve just watched a film for two hours that you were bored silly with, but it’s the bravest film I’ve ever seen. Another was The Tin Drum. A German film, I saw it in New York, thinking it was a war film, which it was in a way. It had subtitles, and after ten minutes I knew what was going on and I stopped reading. But I thought, wow, that’s a film. It’s a film about a broken Germany. It’s quite an incredible piece of work and it changed my opinion about what a film is and should be.

Ray wears Coat Vintage, Suit Shirt by Tailour, Tie vintage, Glasses by Jacques Marie Mage // 📸 : Gavin Bond
Ray wears vintage coat, suit and shirt by Taillour, vintage tie, glasses by Jacques Marie Mage // 📸 : Gavin Bond

What is your favorite word or saying?

(Starts laughing) Well, it means so much… It can be said in so many ways in English… It’s a word that is hated in America.. It’s c*nt!

You know, “I love you, you c*nt!” “You’re such a c*nt!” But you can say it in so many ways… it can be beautiful. It’s only how we perceive it, you know. It’s like Lenny Bruce used to say — if you say the word enough, it doesn’t mean anything anymore. It’s a word I try not to use in public very often, but it’s part of our language where I’m from. A lot of people would say that’s because your language is not very intelligent, well, maybe that’s true, but it says so much. I can get hold of my mate and go, “Come here you c*nt, I love you!” For me, I’ve got to say that.

What do you want people to say about you at your funeral?

It doesn’t really matter because I won’t be there. It’ll be nice if people think of me as a friend. Who was loyal to them, as much as they had been loyal to me. That’ll do. That’ll be alright. And that I’m loved. It’s nice if your family, and the people you love, loved you. That’s enough.

Ray wears Hat by Herbert Johnson, Coat and Scarf by Connoly // 📸 : Gavin Bond
Ray wears hat by Herbert Johnson, coat and scarf by Connolly // 📸 : Gavin Bond

And finally a quickfire five favorites?


I’ve always loved the Jaguar. I’ve owned Jaguars since I was a kid. I’ve had old banger ones. There’s something about a Jag, you can have a pair of old jeans on but still feel alright. You know, with a Rolls Royce, you’ve probably got to have a suit on, but with a Jag, you get in and all the wood and the leather smells beautiful. You can have your jeans on and a baggy shirt and it still feels okay. There’s something about a Jag that I’ve always loved. I guess it’s a poor man’s Aston Martin now, isn’t it? The same shape, but cheaper. I’ve always loved a Jag.

Sports team?

There’s only one, mate — the old Claret and Blue Army, West Ham.

Ray wears Suit Shirt by Tailour, Tie vintage, Glasses by Jacques Marie Mage // 📸 : Gavin Bond
Ray wears suit and shirt by Taillour, vintage tie, glasses by Jacques Marie Mage // 📸 : Gavin Bond


Indoors, it’s river roast beef, roast potatoes, Yorkshire pudding, carrots in honey, cauliflower cheese, Army and Navy gravy, horseradish. Done! That’s me. I’m a bit partial to the Dijon mustard too, funnily enough, rather than the English, which is a bit unusual for me to go for the French rather than the English.

Grooming product?

Cartier aftershave, beautiful. I’ve been using it for years and years — they call it Declaration. I’m turning very French (laughs) Oo La La.

Clothing label?

I don’t mind a bit of Ralph (Lauren) in the summer. You know for us big boys, they seem to fit us better. There’s a shirtmaker called Frangipani, have you seen them? Linen shirts, really light. But in the winter, overcoats, zip-ups, and all that.

Styling by Greg Chapman
Grooming by Oliver J. Woods using Oliver J. Woods products
Photo Assistance by Brandon Hepworth

John is a world-renowned male model who has been the face of countless leading fashion houses. During his 36-year modeling career he has also moonlighted as an actor, writer, restauranteur, editor, and producer. He co-founded Mr Feelgood to provide a safe space for candid discussion and sharing ideas.

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