The first trailer for Guy Ritchie’s latest gangster caper, The Gentlemen, is a pretty accurate reflection of the eight-episode Netflix series, a spin-off of his 2019 film. The director’s usual preoccupations are present — old money and modern criminality, the drugs trade and boxing, cross and double cross. Then comes the big reveal, the one designed both to set audiences at ease and make them punch the air: the unmistakable, bearish figure of Ray Winstone.

There is something reassuring about Winstone in the flesh, too. It’s easy to imagine the 67-year-old holding court in his gruff cockney tones at Raymondo’s, the bar in the Essex home he shares with his wife Elaine, displaying all the quiet authority and easy charm of a man with no end of stories and nothing to prove. Although the latter, he will explain during our conversation in a London hotel, was not always the case.

“The series is proper,” he says, putting down the vape he has adopted after 45 years of cigarettes. “It’s tongue in cheek too, because usually that stuff is very real and can become very boring. Sometimes you need to laugh. And God, if prison was like it is for [my character] Bobby Glass — open air, barbecued steak — I’d be there tomorrow. Few people I’d like to iron out first, mind.”

Glass is a genial hardman whose light-touch incarceration has diminished neither his latent menace nor his cannabis empire, now run by his daughter (Kaya Scodelario), a femme fatale for Theo James’s reluctant heir to a fortune. For Winstone, an actor with a CV full of wrong ’uns, is Glass much of a stretch?

Ray Winstone, wearing coat and sunglasses, sits at an outdoor table where there is a joint of meet. Kaya Scodelario and Theo James sit either side of him
Winstone in ‘The Gentlemen’ with co-stars Kaya Scodelario and Theo James
Ray Winstone, with long hair and beard, stands next to Angela Bassett on board a ship
As Lord Bayford in ‘Damsel’, with Angela Bassett as Lady Bayford

“No, it’s fine,” he shrugs. “Gangsters are hero-worshipped and they shouldn’t be, you know? They come in all shapes and forms — look at these country manors which came out of murdering and robbing in the empire days. Some of the biggest gangsters don’t come from where I come from. They’re on Wall Street.”

A day after The Gentlemen arrives on Netflix comes Damsel, a fantasy romp in which Winstone plays Lord Bayford, who, in the process of marrying off his daughter (Millie Bobby Brown), drags her into an ancient debt involving a dragon. “There were no egos, which surprised me,” says Winstone of the shoot. “I thought Netflix would be on your case all the time, but we were free to go to work.”

Both are supporting roles that an actor of Winstone’s presence makes something of, even on cruise control, but they’re not exactly Nil by Mouth or Sexy Beast. “Listen, if the role’s good enough, it’s big enough,” he reasons. “I’ve got leading roles in me, of course I have, otherwise I’d just stop, but it’s somebody else’s turn.”

Always an unlikely star, young Ray used to perform in a Beatle wig to impress girls in front of his family’s east London home. But it wasn’t his first choice: “I’d rather have been with all the boys, playing football.”

His parents nudged him into acting “to get me off the streets” after seeing him in a school play he joined also in pursuit of a girl. He later enrolled at drama school, only to be expelled for vandalising the head teacher’s car. That same day, Winstone visited a schoolmate auditioning for Alan Clarke’s uncompromising borstal drama Scum at the BBC. It was 1977. Having talked his way into the room, he walked his way into the leading role of Carlin with the swaggering gait he’d acquired as an accomplished teenage boxer. Banned by the BBC, Scum was remade two years later for cinema and Winstone belatedly got his break.

A young Ray Winstone stands in a bathroom, holding a handful of cash, threateningly close to a nervous-looking Patrick Murray
Winstone and Patrick Murray in a scene from ‘Scum’ (1979) © Shutterstock
Ray Winstone sits holding a mug in a kitchen. Kathy Burke sits next to him, smoking a cigarette
With Kathy Burke in Gary Oldman’s 1997 film ‘Nil by Mouth’ © Alamy

“My whole career is down to getting expelled,” he chuckles, quick to credit good fortune over ability. “I had no idea what I was doing, but I was lucky to have Clarkey because he cared about me, a little fucking toerag. There was something about him I thought was honest and real, so I took it in.”

Also in 1979, Winstone appeared in the mod movie classic Quadrophenia and seaside drama That Summer!, where he met Elaine (they have three daughters, actors Jaime, Lois and Ellie Rae). Yet despite a Bafta nomination for the latter, Winstone got stuck as a jobbing TV actor until the 1990s. Partly it was off-screen carousing (“I was a bit of a lunatic”), but also a niggling sense of imposter syndrome.

“I thought people like me didn’t do acting — I was a bit lost and just didn’t feel accepted. I used to go out with the sparks and riggers because I had nothing in common with actors. I was questioning myself: the way I talk, where I’m from, should I really be in this game? . . . You have moments of crisis, I guess, and I’m not sure I’ve ever really thought I’m good at it, just that I’ve got something different to offer. Some people like what you do and some don’t. You’ve got to be all right with that.”

Did he worry his moment had passed? “Yeah, it went a bit pear-shaped for a while,” he admits. “If I’d got famous then, I might be dead now. Who knows? Probably done me the world of good in hindsight. You get kicked in the nuts and realise it ain’t that easy, you know? You fall out of favour or you’re not doing your homework, not conducting yourself right because you’re too busy enjoying yourself. I don’t regret that, but I understand now what was going on a little bit.”

A man in sunglasses with his mouth open
Ray Winstone photographed for the FT by Ollie Adegboye

It took a return to theatre to instil the discipline to accompany his talent, then Gary Oldman — “probably the best director I’ve ever worked with” — to remind us, and perhaps Winstone himself, what he was capable of on screen. His Bafta-nominated performance in Nil by Mouth (1997) as Ray, husband of Kathy Burke’s Val, dredged the humanity from an abusive monster.

“Roles like that are like therapy, in a way,” he says. “You get rid of it on screen, then you don’t need it when you get home. Learning about it, talking to people who have suffered from it . . . it stands you in good stead to be a man for the rest of your life.”

High-profile excavations of masculinity followed, with perhaps the apotheosis coming in Tim Roth’s The War Zone. His role as the local life-and-soul conducting a violently incestuous relationship with his daughter is, says Winstone with a characteristic blend of mischief and honesty, the closest of all to who he really is.

“I’m saying it for effect, I suppose,” he admits, “but I played me to a certain point. You had to recognise the geezer who tells stories to his kids and laughs, and times are hard, but he looks after you. You kind of fall in love with him, then he does something: how do you feel about him now?”

Ray Winstone, wearing swimming shorts, sits in an inflatable floating armchair in a pool, next to a camera and crew on a deck
Filming Jonathan Glazer’s 2000 debut feature ‘Sexy Beast’ © Alamy

Jonathan Glazer’s feature debut, Sexy Beast (2000), offered Winstone both mild reinvention and an entrée to Hollywood. Having rejected the role of psychotic gangster Don Logan (played unimprovably by Ben Kingsley), retired thief Gal Dove was a more muted and melancholy twist on the career criminal. Winstone has remained in demand ever since, working with Martin Scorsese, Steven Spielberg and Darren Aronofsky as well as in more wayward ventures (Cats, The Sweeney) and under-the-radar gems (Jawbone, The Proposition).

Future projects include a “very surreal” biopic of maverick snooker player Jimmy White and a film with Fred Schepisi, director of 2001’s Last Orders, but there will be no follow-up to his early-years memoir Young Winstone.

“What are you gonna write about doing films?” He rumbles with laughter, proffering a hand as he leaves. “‘I met him, then I met her?’ The best stories, you can’t tell . . . ”

‘The Gentlemen’ is on Netflix from March 7; ‘Damsel’ from March 8

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