Ray Winstone's Three Heartbreaking Movies

Ray Winstone, the gravel-voiced British icon known for playing tough, no-nonsense characters in films like Sexy Beast, The Departed, The Gentlemen, and Nil by Mouth, has built a reputation as one of cinema’s most intimidating presences. Yet behind the tough exterior lies a deeply emotional man who isn’t afraid to admit when a story brings him to tears. In various interviews over the years—including a candid 2019 chat with The Guardian and more recent reflections resurfaced in early 2026—Winstone has openly shared the three films that consistently “absolutely break my heart” and reduce him to tears every time he watches them.

These aren’t obscure arthouse picks; they’re powerful, mainstream stories that resonate on a profoundly human level. Winstone has said he can’t help but get emotional because they touch on universal themes of family, loss, regret, and the quiet dignity of ordinary people—ideas that hit close to home for a man who grew up in a working-class East London family and has carried those roots throughout his career.

1. Kes (1969) – Directed by Ken Loach

Winstone has repeatedly named Ken Loach’s Kes as the film that “absolutely breaks my heart” more than any other. The story of Billy Casper, a neglected working-class boy in Yorkshire who finds fleeting joy and purpose through his bond with a kestrel hawk, only to have it cruelly taken away, strikes a deep chord. Winstone has described it as “devastating” and said he cries “like a baby” every time he sees the ending.

The film’s raw depiction of poverty, bullying, and a child’s fragile hope in a harsh world reminds Winstone of his own upbringing and the struggles many face. He’s called it “the most heartbreaking thing I’ve ever seen on screen,” praising Loach’s unflinching honesty and David Bradley’s heartbreaking performance as Billy. For Winstone, Kes isn’t just a movie—it’s a mirror to the pain and resilience of ordinary lives.

2. The Champ (1979) – Directed by Franco Zeffirelli

The second film Winstone says always gets him is The Champ, the remake of the 1931 classic starring Jon Voight as an aging, alcoholic boxer trying to win back the love of his young son (Ricky Schroder). The story builds to one of the most emotionally wrenching endings in cinema history, and Winstone admits it leaves him in pieces.

He’s spoken about how the father-son dynamic, the theme of redemption, and the tragic inevitability hit him hard. “It’s the one where the kid says ‘Champ, wake up’—that kills me,” Winstone has said. The raw vulnerability of Voight’s performance and the innocence of Schroder’s child character create a perfect storm of heartbreak for the actor, who is himself a devoted father.

3. Marley & Me (2008) – Directed by David Frankel

Perhaps the most surprising entry on Winstone’s list is Marley & Me, the family comedy-drama starring Owen Wilson and Jennifer Aniston about a chaotic Labrador retriever who brings joy, chaos, and ultimately profound sorrow to a family. Winstone has confessed that the film’s final act—when the aging Marley must be put to sleep—leaves him sobbing uncontrollably.

He’s called it “a proper cry movie” and said it reminds him of the unconditional love pets give and the pain of saying goodbye. In interviews, he’s joked that he has to “hide in the toilet” when the scene comes on, but the tears are real. For a man who’s played hardened criminals and gangsters, admitting that a dog movie makes him cry is refreshingly honest—and relatable to millions who’ve experienced the same loss.

Why These Choices Reveal So Much

Winstone’s three tear-jerkers share common threads: they focus on family bonds (biological or chosen), the fragility of hope, and the quiet devastation of loss. They avoid melodrama in favor of raw, authentic emotion—qualities Winstone values in acting and in life. He’s said these films remind him that “life’s too short” and that real strength lies in vulnerability.

In an industry where tough-guy personas often come with emotional armor, Ray Winstone’s willingness to share his soft spots feels genuine and endearing. The same man who can intimidate on screen isn’t ashamed to admit when a story “absolutely breaks my heart.” It’s a reminder that behind every hard man is someone who feels deeply—and sometimes, that’s the most powerful performance of all.

Source - https://faroutmagazine.co.uk/the-three-movies-that-make-ray-winstone-cry/

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