How Sylvester Stallone Conquered Hollywood And Never Looked Back

Just try avoiding Sylvester Stallone these days.

The screen legend’s new memoir, “The Steps,” shares intimate tales of his remarkable life. His Paramount+ show “Tulsa King” is still going strong, even expanding with “The Frisco King,” a spin-off starring Samuel L. Jackson.

His breakthrough film, 1976’s “Rocky,” will be re-released in theaters November 7-11 to honor its 50^th anniversary. The day before, his signature film gets a Hollywood close-up with “I Play Rocky” (November 20), a film arriving with heaps of awards season buzz.

How many 80-year-old stars have impacted the culture this long, and, more importantly, in such a positive way?

Stallone’s origin story is so improbable they literally made a movie about it, brought to the big screen with Anthony Ippolito playing the young Stallone in “I Play Rocky.” Stallone wrote the screenplay for the original “Rocky,” envisioning it as his first starring role. The film’s producers had other ideas, hoping to snag an established star like Burt Reynolds or James Caan.

At the time, Stallone was a struggling actor who was so poor he claims he sold his dog for cash, and he could have snagged a sizable check for the screenplay alone and let someone else play Rocky Balboa.

But Stallone held his ground, and the rest is Hollywood history.

The film proved a template for anyone hungry for their American Dream. If this no-name boxer could earn a shot at the title, let alone woo the shy girl in town, anyone could TKO the obstacles in their way.

That’s why Stallone has been an inspirational figure far beyond his screen status. He’s leaned into that role over time, telling fans to “keep punching” and playing up his underdog saga.

It’s hard to say how many lives have been impacted through both “Rocky” and its iconic theme music, “Gonna Fly Now” by Bill Conti.

We know Stallone’s films inspired one father to share his “Rocky” love with his son. The lad, nine-year-old Ro Knight, went viral three years ago when he recited a speech from 2006’s “Rocky Balboa” to Stallone himself during a public appearance.

“Let me tell you something that you already know, the world ain’t all sunshine and rainbows…” the boy excitedly told the Hollywood legend, who beamed in response and began reciting the latter part of the speech alongside him.

Stallone didn’t stop at one indelible franchise (he directed and co-wrote multiple “Rocky” sequels). He also gave voice to disaffected soldiers who felt betrayed by their country’s Vietnam War policies with “First Blood” (1982), the first John Rambo feature.

That saga spawned four sequels and a prequel currently in production (Stallone won’t appear but serves as an executive producer).

Stallone’s career featured more highlights, including “Cop Land” (1997), one of his best performances, and a Best Supporting Actor Oscar nomination for “Creed” (2015).

It wasn’t all sunshine and rainbows, of course. Stallone’s epic duds include “Oscar” (1991), “Stop! Or My Mom Will Shoot” (1992), “Rhinestone” (1984), and “Driven” (2001). He recently admitted to suffering from bulimia and using steroids to build the physique we saw in his “Rocky” and “Rambo” features.

His love life proved similarly rocky, although he’s been married for 29 years to Jennifer Flavin.

The “Creed” saga said goodbye to an aging Rocky Balboa in “Creed III,” but Stallone found another signature part with Paramount+’s “Tulsa King.” He plays a former New York City mobster who sets up shop in Oklahoma.

The show, part of the Taylor Sheridan universe, leans on his tough-guy image and ageless charisma. The show is slated for a fourth season.

In another era, retreating to television would be seen as a demotion. Today, with streamers dominating pop culture, Stallone’s transition made perfect sense.

Stallone has spent his career avoiding politics, unlike many of his A-list peers. Some suspected he leaned to the Right, given films like the “Rambo” saga, which took the fight to terrorists sans pearl-clutching, and his embrace of the American spirit.

He let his films speak for him until a real estate mogul won the White House a second time.

His praise of President Donald Trump shortly after the 2024 election shocked many Hollywood observers. Embracing Trump can hurt a star’s career. Just ask Cheryl Hines, who hasn’t had a major Hollywood gig since her husband, Robert F. Kennedy, Jr. aligned with the former and future president two years ago.

Other actors keep their views quiet, meeting in secretive groups like Friends of Abe to share stories of being ostracized for their right-leaning views.

But Stallone is too big to cancel, and he knows it. By speaking up, he gave less famous actors cover to do the same.

That’s true Hollywood courage.

The film industry remains undeniably cruel. The biggest stars can find their red-hot careers fading with time. Fickle audiences prefer muscle-bound action heroes one decade, then opt for lean actors with names like Chalamet, Holland, and Reeves the next.

For every enduring icon like Clint Eastwood, countless stars are left to pick scraps from the casting agent’s file cabinet — if they’re lucky.

Not Stallone. And retirement doesn’t appear to be an option for the Italian Stallion. He’s working on a director’s cut of “Rocky V,” the most disappointing film in the series. And Balboa Productions just re-upped its deal with Amazon MGM for future films and TV projects.

Stallone. Keeps. Punching.

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Christian Toto is an award-winning journalist, movie critic and editor of HollywoodInToto.com. He previously served as associate editor with Breitbart News’ Big Hollywood. He’s also the host of The Hollywood in Toto Podcast. Follow him at @HollywoodInToto.