Sylvester Stallone Still Cringes Over Judge Dredd: “The Biggest Mistake I Ever Made”

Sylvester Stallone’s legacy in Hollywood is carved in stone—Rocky and Rambo alone have secured his place as one of cinema’s most enduring action icons. But even for a star of Stallone’s stature, not every role is a knockout. In fact, the actor is refreshingly candid about the films he wishes he’d never made, and at the top of that list sits one of the most notorious misfires of the ’90s: Judge Dredd.

Speaking to We Got This Covered, Stallone rattled off several career regrets—movies that tanked both critically and commercially. While modern audiences might point to recent duds like Samaritan, Stallone’s personal list leans further back, spotlighting films like Rhinestone (1984), Stop! Or My Mom Will Shoot (1992), and Driven (2001).

Some of these flops come with bizarre backstories—like Stop! Or My Mom Will Shoot, which Stallone was tricked into making by his then-rival Arnold Schwarzenegger. During a 2017 Q&A at Beyond Fest, Schwarzenegger gleefully admitted to pretending he was interested in the project just so Stallone would swoop in to “steal” it. “And he went for it! A week later, I heard, ‘Sly is signing now to do this movie.’ And I said, [pumps fist] ‘Yes!’” Schwarzenegger laughed.

Then there was Rhinestone, a country-musical comedy co-starring Dolly Parton, which Stallone hoped would have an edgier soundtrack—he even approached Whitesnake’s management at the time. Instead, the film veered into what Stallone now describes as a tone that “shattered my internal corn meter into smithereens.”

But nothing haunts him quite like Judge Dredd. Released in 1995, the comic-book adaptation was savaged for its campy tone, muddled storytelling, and Stallone’s decision to spend most of the film with his helmet off—a cardinal sin to fans of the source material.

“The biggest mistake I ever made was with the sloppy handling of Judge Dredd,” Stallone has said. “It could have been a fantastic, nihilistic, interesting vision of the future—judge, jury, and executioner. That [film] really bothered me a great deal… I thought it was a fantastic concept, but somebody has to take the fall when things don’t work—and because I was the most recognisable, highest profile, that somebody was me.”

Nearly three decades later, Stallone’s candor about his misfires only cements his reputation as a self-aware Hollywood veteran who can own his failures as openly as his triumphs. And while Judge Dredd may still make him wince, fans can rest assured that the man who brought Rocky Balboa to life knows exactly when he’s been knocked down—and how to get back up again.

If you want, I can also create a full retrospective listicle ranking all of Stallone’s “regret” films with behind-the-scenes trivia and cultural context—it would make for a great companion piece.