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

Ray Winstone might cop a bit of stick for his tough-guy image and gravelly voice, but there’s no denying he’s carved out a legendary career. While he’s often cast as the hard bloke, his filmography is surprisingly broad, stretching from big-budget blockbusters to indie flicks, comedies, animations, and even the odd musical. It’s a reminder not to judge a book by its cover, even if that book looks like it could knock your block off.

Over the years, Winstone has worked with some of the biggest names in the business. He’s shared the screen with the likes of Matt Damon, Mark Wahlberg, and Leonardo DiCaprio in Martin Scorsese’s The Departed, and even had a stint alongside Jack Nicholson—though he’d be the first to admit that wasn’t quite as glamorous as it sounds. Whether it’s Hollywood or homegrown productions, Winstone’s got a stack of stories about working with the best in the game. But there’s one film that stands out for him, where he got to tick off not one, but two of his all-time heroes.

Meeting Legends on Set

Chatting about his time on the 2001 drama Last Orders, Winstone recalled being cast as the son of Michael Caine’s character. Despite never having met before, Caine made a real effort to 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 remembered.

“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 simply:

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

Bringing a Booker Prize Story to Life

Last Orders, based on the Booker Prize-winning novel, is a raw and heartfelt tale about the final wish of Jack Dodds, a working-class bloke played by Caine. After his death, it’s up to his old mate (Hoskins), his estranged son, and a handful of others whose lives he touched to scatter his ashes at sea. On paper, it might sound a bit sentimental or even predictable, and there’s some truth to that. But the strength of the cast—including Tom Courtenay and Helen Mirren—and the sharp writing won over heaps of viewers.

Winstone, Caine, and Hoskins all share a similar background. Though Hoskins hailed from Suffolk, all three grew up in London, a city that would shape their careers for decades. Each made a name for themselves playing everyday Londoners, often with a tough edge, and delivered standout performances as no-nonsense types in films that are still held up as classics.

A Unique Gathering of British Icons

This film marked the only time these three British legends appeared together on screen before Hoskins’ passing in 2014. Regardless of what punters reckon about the film itself, the fact it brought together such a fascinating trio is reason enough for it to be remembered.