Ray Winstone Worked with Heroes in Last Orders

British acting legend Ray Winstone has shared countless stories from his decades in the industry, but one stands out as truly special: the day he got to work alongside two of his lifelong heroes in the same film. In a heartfelt interview with Shortlist (later revisited in various outlets), Winstone recalled his experience on the 2001 drama Last Orders, directed by Fred Schepisi and based on Graham Swift's Booker Prize-winning novel.

The film follows a group of working-class Londoners fulfilling the final wish of their late friend Jack Dodds (played by Michael Caine): to scatter his ashes in Margate. Winstone portrays Vince Dodds, Jack's estranged son, in a poignant story of friendship, regret, and legacy. Joining Caine in the ensemble are Bob Hoskins (as Ray, Jack's best mate), Helen Mirren, David Hemmings, and Tom Courtenay.

For Winstone, landing the role was already a dream come true. “I remember finding out I was gonna do Last Orders,” he told Shortlist. “And they said, ‘By the way, you're playing Michael Caine's son.’” The news hit hard—he'd grown up idolizing Caine, one of Britain's most iconic actors, known for everything from The Italian Job to Alfie and Get Carter. “I thought, ‘Blimey, I'm playing Michael Caine's son!’”

What made the experience even more extraordinary was discovering Bob Hoskins was also in the cast. Winstone had already worked with Hoskins on several projects, including The Long Good Friday and others, and held him in the highest regard. “Bob, I was lucky to work with on three or four occasions, once as a director as well,” he reflected.

The set became a masterclass in camaraderie and respect. Caine, the elder statesman, went out of his way to make Winstone feel welcome. “He was good as gold. He was lovely,” Winstone said. The two had never met before, yet Caine's warmth and professionalism immediately bridged the gap. Hoskins, already a familiar face, added to the easy rapport.

Winstone summed up the joy of the experience with genuine affection: “I can’t tell you what a ball I had with these guys. Proper men. I loved them all.”

What Makes “Proper Men” So Meaningful

In Winstone's world, “proper men” isn't just casual praise—it's the highest compliment. It evokes authenticity, toughness tempered with kindness, and the kind of old-school working-class integrity he grew up around in East London. Caine and Hoskins embodied that: both self-made stars from humble beginnings, both commanding respect without ego, both masters of their craft who treated everyone on set with decency.

The film itself mirrors those qualities. Last Orders is a quiet, emotional road movie about ordinary men confronting mortality, friendship, and the passage of time. Caine's Jack is a stoic butcher who quietly shaped the lives of those around him; Hoskins' Ray is the loyal, wisecracking pal who keeps spirits up. Winstone's Vince, the estranged son, carries the weight of unresolved family pain, making the generational dynamic feel deeply personal.

Working with both icons in one project allowed Winstone to pay homage to the actors who'd influenced him while contributing to a film that celebrated exactly the kind of “proper” masculinity he admired—unpretentious, loyal, and heartfelt.

Legacy of the Experience

Last Orders (2001) received strong reviews for its ensemble performances and gentle humor, earning praise at festivals and a solid place in British cinema. For Winstone, it remains a highlight in a career filled with tough-guy roles (Sexy Beast, The Departed, Beowulf). He often cites it as proof that the best days on set come from mutual respect and shared craft.

In a later reflection, Winstone noted how rare it is to work with heroes without disappointment. Caine and Hoskins exceeded expectations—professional, generous, and utterly “proper.” It's a story that reminds us why Winstone remains one of Britain's most beloved actors: grounded, grateful, and always ready to celebrate the legends who paved the way.

Source - https://faroutmagazine.co.uk/the-remarkable-day-ray-winstone-worked-with-both-of-his-heroes/

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