Friday, October 24, 2025

Matt Dillon Cast as Sylvester Stallone’s Tough Father in I Play Rocky

Matt Dillon will take on the role of Frank Stallone Sr., Sylvester Stallone’s father, in the upcoming Amazon MGM Studios production titled I Play Rocky. This film offers an intimate behind-the-scenes look at how one of the most iconic underdog stories in cinema was brought to life.

Overview of the Film and Its Creative Team

Directed by Oscar-winning filmmaker Peter Farrelly, known for Green Book, I Play Rocky stars Anthony Ippolito as a young Sylvester Stallone. Written by Peter Gamble, the film narrates Stallone’s relentless pursuit to star in and write the original Rocky, focusing on his determination in the face of repeated setbacks.

The story is described as

“an electrifying true story about an unknown actor with an unshakable belief that he wasn’t just meant to write Rocky — he was meant to be Rocky Balboa,”

capturing Stallone’s ambition and resolve.

Character Study: Frank Stallone Sr.’s Complex Role

Frank Stallone Sr., the character Matt Dillon portrays, was a layered individual who immigrated to the U.S. from Italy as a teenager. He built a successful career as a hairdresser and entrepreneur, establishing multiple salons and beauty schools along the East Coast. However, he was also known as a strict and often harsh father.

In the 2023 documentary Sly, Stallone reflected on his father’s tough demeanor, saying,

My father was Rambo in reality. Nothing was ever settled verbally.

– Sylvester Stallone

The complex father-son relationship is a significant emotional thread in I Play Rocky, highlighting Stallone’s constant desire for his father’s approval despite their difficulties. Their strained connection even made its way into the original 1976 Rocky, where Frank Stallone Sr. appeared briefly as a timekeeper.

Matt Dillon
Image of: Matt Dillon

Supporting Cast and Production Details

The cast includes Stephan James as Carl Weathers, the actor famed for portraying Apollo Creed, and AnnaSophia Robb as Sasha Czack, Stallone’s first wife. The production is overseen by Toby Emmerich and Christian Baha, with FilmNation Entertainment providing production services and managing international sales.

Matt Dillon’s Career Highlights Leading to This Role

This role represents a return to intense and nuanced drama for Matt Dillon, who earned an Oscar nomination for his performance as Officer John Ryan in Crash. His extensive career showcases his versatility across genres, from dramatic films like The Outsiders, Rumble Fish, and Drugstore Cowboy to comedic hits such as There’s Something About Mary.

Recently, Dillon has appeared in Wes Anderson’s Asteroid City and the Apple TV+ series High Desert, demonstrating his continued relevance and adaptability in film and television.

Why This Film Matters for Cinema and Fans

I Play Rocky promises to delve deeply into the emotional and personal struggles behind the creation of a cinematic legend, exploring themes of ambition, family tension, and legacy. By portraying Frank Stallone Sr., Matt Dillon brings to life a pivotal figure who influenced Sylvester Stallone’s drive and resilience. For audiences, this film offers a fresh and earnest perspective on the story of how Rocky came to define an era of underdog inspiration in Hollywood.

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