Ray Winstone and Guy Ritchie on the set of The Gentlemen season two Given Ray Winstone’s background in the gangster movie genre, it’s hard to believe that his work in Netflix’s The Gentlemen marks his first time collaborating with director Guy Ritchie. Back in 2024, following the release of season one, Ray told Men’s Health magazine that he and Guy’s paths had actually first crossed years earlier, when he almost landed a role in Lock, Stock And Two Smoking Barrels. However, this didn’t end up happening, with the British actor admitting that he and the filmmaker had a major fall-out around this time. “We were younger kids, arguing, and kind of fell out,” he recalled, admitting that he continued to watch Guy’s career blossoming from afar. “It’s a shame, because over the years I watched his films and, you know, begrudgingly liked them,” he joked. Ray Winstone at the premiere of The Gentlemen season two earlier this month During a subsequent interview with the same magazine published in September, Ray revealed that mutual friends had encouraged the two men to meet up and clear the air, which is how they came to finally work together. “We had a chat,” Ray said. “I suppose it’s part of growing up – becoming a man instead of a silly little boy. We had a little chat and a little hug, as you do in the film business.” Ray added that finally working with the Snatch director definitely lived up to his expectations and he “really enjoyed” the experience. He also opened up more on the subject during a chat with Esquire magazine, saying: “When I was younger, something happened. I just didn’t like the way... the film was put on hold and I took umbrage to the fact that no one was told. “These actors, this crew, have rents to pay. And if it’s been put on hold and the money’s not coming through for a film, tell everyone. They’ve got a choice then – go and find some more work or whatever.” Ray admitted: “I just thought it was a liberty. I aired my opinion, said, ‘See you later.’ Then, we had words a bit later on. I didn’t like what he’d done. There’s a way of going about your business, and I’ve probably got the wrong end of the stick anyway. But anyway, it was done, it was said, move on.” Guy Ritchie While he claimed that he could previously have “never” imagined working with Guy again, he conceded: “Then you watch what he’s doing. You know a Guy Ritchie film when you watch it. He’s not copying anyone. He does what he does, and the more you get to know him, the more challenging you realise he is.” “When it came through that he was interested in me doing [The Gentlemen[, I thought I owed him to go and see him and talk to him about it,” he continued. “And we had a little cuddle. And it was all right. “I’m glad that did happen, because you can’t go on [carrying a grudge]. When you’re kids, you do things, don’t you?” Ray has now played Kaya Scodelario’s on-screen father, the formidable Bobby, in both seasons of The Gentlemen. He is expected to return for the show’s third outing, which was confirmed to be in the works last month. READ MORE: There's Good News And Bad News For Anyone Already Hoping For The Gentlemen Season 3 Thought The New Stars Of The Gentlemen Season 2 Looked Familiar? Where You've Seen Them Before Netflix Exec Breaks Silence On Rumours Meghan Markle The Gentlemen Season 3 Rumours