Sylvester Stallone Reveals the Heartwarming Story Behind His 50-Year Friendship with Henry Winkler

Sylvester Stallone and Henry Winkler’s enduring friendship, forged in the early days of their careers, has become one of Hollywood’s most cherished relationships. Their bond began in 1974 on the set of The Lords of Flatbush, a coming-of-age drama about a Brooklyn street gang. The two young actors, navigating their careers at the time, never imagined that this collaboration would mark the start of a deep, lifelong friendship.

Reflecting on the 50th anniversary of The Lords of Flatbush in May 2024, Stallone described the experience as “a journey of friendship, growth, and passion,” emphasizing the profound bond they developed over the years. “Half a century of cherished moments and lifelong bonds,” he said, underscoring the depth of their relationship, which has weathered decades of personal and professional changes.

Beyond their initial collaboration, Stallone and Winkler’s friendship grew stronger, particularly during Stallone’s struggles in the early years of his career. As Stallone worked relentlessly on his script for Rocky, he shared his progress with Winkler, who was at the height of his fame as The Fonz on Happy Days. At a time when Stallone faced uncertainty about his future, Winkler became a crucial ally. Winkler took the script to ABC, where initial reactions suggested Stallone might not get the credit he deserved. But with Winkler’s influence, he convinced the network to keep Stallone’s name as the credited writer, a pivotal act that ultimately contributed to Rocky’s success.

Winkler has consistently expressed admiration for Stallone, calling him “brilliant, dry and funny, so literate,” further solidifying the respect and support that have defined their relationship. This loyalty and support extended beyond the professional, becoming a cornerstone of their friendship.

In recent years, their bond remains as strong as ever. In September 2023, they were spotted enjoying pizza together in Beverly Hills, with Winkler sharing that he frequently calls Stallone to debrief on each episode of Tulsa King. These simple but significant moments—often shared with the public through social media posts and selfies—illustrate a friendship that thrives in both casual interactions and heartfelt conversations.

Their friendship isn’t just about Hollywood glamour; it’s rooted in shared history and personal memories. Stallone has recalled moments such as inviting Winkler to his New York apartment, where he lived with his first wife, Sasha, and their bullmastiff. The windows of the apartment were painted black so that Stallone could work without distractions—a detail Winkler fondly remembers, encapsulating the intimate side of their connection.

The longevity and warmth of their friendship has not gone unnoticed. In 2023, Winkler appeared in a Netflix documentary about Stallone, discussing their early days and the personal bond that has withstood the test of time. Public reunions, including a 2024 lunch selfie that circulated on Reddit, continue to highlight the enduring nature of their camaraderie, with fans and media alike celebrating their special relationship.

In a world where Hollywood friendships can sometimes be fleeting, the bond between Stallone and Winkler stands as a testament to loyalty, mutual respect, and shared history. What began as a professional collaboration on The Lords of Flatbush has evolved into a friendship that has spanned over five decades, proving that sometimes the most meaningful connections are the ones that last a lifetime.