From Rocky to Rambo: Stallone’s 25 Screenplays — And the Artistic Battle He Fights With a Brush

Sylvester Stallone is best known as the underdog who created and embodied Rocky Balboa, but behind his iconic on-screen toughness lies a lifelong struggle with another craft: writing. Over the course of his career, Stallone has penned more than 25 screenplays, shaping the Rocky, Rambo, and Expendables franchises. Yet, when reflecting on his creative journey, the actor revealed that his most enduring artistic battle doesn’t happen in a boxing ring or on a film set — it happens in front of a canvas.

“The canvas feels like an enemy — I fight it with brushes,” Stallone confessed in a 2021 interview with Artnet, describing his intimate relationship with painting.

Loneliness Fueled His Ambition

Stallone’s drive was born out of solitude. In a recent interview with TODAY, he recalled his early years in New York, where chasing acting dreams left him isolated.

“I never went to a party, a bar, nothing,” he said. “I went out one time, it was New Year’s Eve 1970. I went to Times Square alone. I looked around and realized everyone here wants to be somebody, so I’d better go home and work hard, ’cause this is your competition.”

That moment of clarity inspired him to work relentlessly, even as he was relegated to typecast roles. Eventually, he realized he needed to create the kind of role no one else would hand him.

The Birth of Rocky

The solution came in the form of Rocky, a screenplay Stallone wrote for himself. Studios loved the story but didn’t want him as the lead. One even offered $360,000 for the script — without him in the starring role.

“This [role] is you, Sly,” he recalled thinking. “If you get rid of this, yes, you’ll have $360 grand, but eventually that will be gone and you will be the most bitter human being because the entire [film] was about not selling out.”

His gamble paid off. Rocky became a cultural juggernaut, earning 10 Oscar nominations, including Best Actor and Best Original Screenplay for Stallone, and winning three Academy Awards, including Best Picture.

The Grind of Writing

Despite his success, Stallone has never romanticized the writing process. “It’s very difficult,” he admitted. “You go into a fog.” Still, he has persisted, writing across multiple franchises that have grossed billions worldwide, cementing his reputation as one of Hollywood’s most prolific multi-hyphenates.

In a 2023 conversation with The Hollywood Reporter, Stallone reflected on his creative limitations. “I didn’t have the bones to be a Shakespearean actor,” he said. “It’s important as an artist to know what your strengths are, but more important to know your weaknesses.”

Fighting With Paint

While films have defined his public image, Stallone finds a different kind of truth in painting. For him, the canvas becomes both adversary and confidant.

“Painting is where I feel close to a bare naked truth,” he explained. “When a painting resists halfway through, I don’t shy back from the conflict. I think and get physical with the brush.”

It’s a fight not unlike the ones his characters face — a struggle for authenticity, honesty, and victory against the odds.

An Artist Beyond the Ring

From Rocky to Rambo, Stallone has built a career on grit, perseverance, and storytelling. Yet his own words reveal that his greatest battles — and triumphs — often happen in silence, brush in hand, locked in combat with a canvas.

For Stallone, the fight never really ends. It just changes arenas.

Would you like me to shape this more as a Hollywood career retrospective or as an arts and culture feature highlighting Stallone’s lesser-known identity as a painter?