Ray Winstone's Dream Day: Working With Two British Icons
The tough-guy actor reveals what it was like sharing the screen with Michael Caine and Bob Hoskins in a single film, calling them 'proper men' who made the experience unforgettable.
People often dismiss Ray Winstone as just another rough-voiced tough guy, but that's selling him short. His resume spans everything from major blockbusters to small indie films, animated features to the occasional musical. The man's range goes way beyond what most people expect.
Throughout his career, Winstone has rubbed shoulders with Hollywood's biggest names. He appeared in Martin Scorsese's The Departed alongside Matt Damon, Mark Wahlberg, and Leonardo DiCaprio. He even worked with Jack Nicholson, though he'd tell you that experience didn't quite live up to expectations.
Meeting His Heroes
But one project gave Winstone something special. The 2001 drama Last Orders let him work with not one, but two of his personal heroes in the same movie.
Talking to Shortlist, Winstone remembered his first encounter with Michael Caine, who played his character's father in the film. Despite never meeting before, Caine immediately put him at ease. "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."
A Perfect Match
"I can't tell you what a ball I had with these guys. Proper men. I loved them all," Winstone said.
Last Orders, based on the Booker Prize-winning novel, tells the emotional story of Jack Dodds, Caine's character, and his final wish. After his death, his oldest friend (Hoskins), his estranged son, and other men whose lives he touched must scatter his ashes at sea. The cast also featured Tom Courtenay and Helen Mirren.
Sure, the plot sounds a bit sentimental on paper. Maybe even predictable. But the powerhouse performances and solid writing won over audiences anyway.
Three London Legends
Winstone, Caine, and Hoskins shared more than just screen time. All three grew up in London, the city that would shape their entire careers. Each made their name playing ordinary Londoners with that unmistakable tough-guy edge. They became go-to actors for no-nonsense gangster roles in films that still set the standard today.
This was the only time these three British legends ever appeared together before Hoskins died in 2014. Whatever you think of the actual movie, it gave us this unique moment when three masters of their craft shared the same frame.