Ray Winstone’s Unforgettable On-Set Encounter With His Idols

Ray Winstone’s reputation often precedes him—gravelly-voiced, a bit of a bruiser, and frequently cast as the hard man. Yet, his career is anything but one-note. From big-budget blockbusters to offbeat comedies and even the occasional musical, he’s managed to sidestep the trap of typecasting more than most would expect. His filmography boasts collaborations with the likes of Martin Scorsese, Matt Damon, and Leonardo DiCaprio, not to mention a memorable stint alongside Jack Nicholson, though he’s been known to downplay that particular experience. Winstone’s journey through the world of film has been peppered with stories of working with some of the industry’s most celebrated figures, but one project stands out for him above the rest.

During a chat with Shortlist, Winstone looked back on his time filming the 2001 drama Last Orders. Cast as the son of Michael Caine’s character, he found himself face-to-face with a legend he’d admired for years. Their first meeting was anything but intimidating.

“He said to me, ‘Now, Raymond. I know you’re probably nervous, working with me. But don’t worry, son, I’ll look after you’,”

Winstone recalled.

“He was good as gold. He was lovely. And then I find out Bob Hoskins is in it. Bob, I was lucky to work with on three or four occasions, once as a director as well”.

He summed up the experience with genuine warmth:

“I can’t tell you what a ball I had with these guys. Proper men. I loved them all.”

London Legends United

Adapted from a Booker Prize-winning novel, Last Orders is a raw, heartfelt tale centred on the final wish of Jack Dodds, a working-class man played by Caine. The story follows a group of his closest friends—including Hoskins’ character—and his estranged son, as they set out to scatter his ashes at sea. On the surface, it might sound a touch sentimental, perhaps even formulaic, but the cast’s collective talent and the script’s emotional honesty struck a chord with audiences.

Winstone, Caine, and Hoskins all share a certain kinship, shaped by their London upbringing. Though Hoskins hailed from Suffolk, the capital left its mark on each of them, influencing the roles they chose and the way they approached their craft. Their careers are littered with portrayals of everyday Londoners—often tough, sometimes vulnerable, always authentic. Each brought a distinctive edge to the screen, particularly in the gangster genre, where their performances remain benchmarks for the style.

A Singular Collaboration

This film marked the only occasion these three British icons appeared together. Hoskins, who passed away in 2014, never again shared a set with Winstone and Caine. The significance of this collaboration isn’t lost on those who appreciate the nuances of British cinema. Whatever one’s opinion of the film itself, the chance to witness this trio in action is reason enough to revisit it.

Alongside Caine and Hoskins, the ensemble included Tom Courtenay and Helen Mirren, further elevating the production. The chemistry among the cast, coupled with the source material’s depth, ensured the film resonated with viewers who value character-driven storytelling over spectacle.

Behind the Scenes: Camaraderie and Craft

For Winstone, the experience was more than just another job. The camaraderie on set, the mutual respect, and the opportunity to work with those he’d long admired left a lasting impression. It’s not every day an actor gets to tick two names off his personal wish list in one go. The memories of those days—shared laughter, quiet moments, and the unspoken understanding between “proper men”—remain vivid for him.

In the end, Last Orders stands as a testament to the enduring appeal of stories rooted in real lives, brought to life by actors who know the world they’re portraying inside out. For Winstone, it was a rare privilege, and for audiences, a glimpse into a unique moment in British film history.