Ray Winstone’s Unforgettable Day on Set With His Acting Idols

Ray Winstone might be best known for his tough-guy persona and gravelly voice, but his career is far more diverse than many realize. From major blockbusters to indie gems, comedies, animated features, and even musicals, Winstone has proven he’s much more than a one-note actor. His filmography includes working with some of Hollywood ’s biggest names, like Matt Damon, Mark Wahlberg, Leonardo DiCaprio, and Jack Nicholson in Martin Scorsese’s The Departed. Yet, for all the stories he could tell about his time in the industry, one project stands out above the rest for a deeply personal reason.

In a conversation with Shortlist, Winstone looked back on his experience filming the 2001 drama Last Orders. Cast as the son of Michael Caine’s character, Winstone was thrilled to finally meet and work with the legendary actor. He recalled,

“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.’ 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.”

The chance to share the screen with both Caine and Hoskins was a dream come true for Winstone, who added,

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

Bringing a Booker Prize Novel to Life

Based on the acclaimed novel, Last Orders tells the moving story of Jack Dodds, a working-class man whose dying wish is for his ashes to be scattered at sea. Michael Caine plays Jack, while Bob Hoskins portrays one of his oldest friends. Winstone steps in as Jack’s estranged son, joining a group of men whose lives were all touched by Jack’s presence. The film ’s premise might sound sentimental or even predictable, but the powerhouse cast and strong writing won over audiences and critics alike. The ensemble also featured Tom Courtenay and Helen Mirren, adding even more depth to the story.

For Winstone, the project was more than just another role. It was a rare opportunity to work alongside two actors he’d admired for years, both of whom had shaped the landscape of British cinema. The camaraderie and respect among the cast made the experience especially meaningful for him.

Legends Shaped by London

Though their backgrounds varied, Winstone, Caine, and Hoskins all shared a deep connection to London, the city that would come to define their careers. Each actor made a name for himself playing everyday Londoners, often with a gritty edge and a knack for portraying no-nonsense characters. Their performances in crime dramas and gangster films set a standard that still resonates today.

Last Orders marked the only time these three icons appeared together on screen. With Hoskins’ passing in 2014, the film stands as a unique snapshot of British acting royalty. Regardless of how one feels about the movie itself, the chance to see these legends interact is a testament to the power of great storytelling and unforgettable performances.