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Sylvester Stallone’s Biggest Career Regret Involves 3 Movies That Should’ve Been Franchises

Even Sylvester Stallone thinks these were missed opportunities.

Sergio PereirabySergio Pereira
August 9, 2026
Tango & Cash Sylvester Stallone Kurt Russell

Image Credit: Warner Bros.

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From Rocky Balboa to John Rambo, Sylvester Stallone knows a thing or two about creating iconic film characters and franchises. Fortune favored him throughout his career, but even he knows he left money on the table with a few of his films – and no, Stop! Or My Mom Will Shoot isn’t included here.

Speaking to GQ , Stallone opened up about three movies he thought could have been turned into trilogies. “My biggest regret is that I didn’t do Cobra as a franchise,” he said. “Tango & Cash and Demolition Man, I felt each one of those had at least three movies in them. But I was just… I guess maybe too lazy. But I didn’t do it. But I felt those films had potential to go on.”

Cobra turned out to be a tidy hit for Sly, making $160 million from a $25 million budget. It didn’t receive great reviews at the time, but when it makes that amount of money at the global box office, who cares what reviewers think, right? Plus, it never gets old seeing Marion “Cobra” Cobretti cutting his pizza with scissors…

Sylvester Stallone Cobra cutting pizza
Image Credit: Warner Bros.

It does feel odd that a sequel never materialized, though, especially since Stallone was a megastar at the time and considering the profit that Cobra made. Having said that, the production company behind the film was the Cannon Group, and yeah, let’s say its track record of making wise business decisions wasn’t all that good in retrospect.

In terms of Tango & Cash, it’s largely the same deal. It was not well received by critics, but it made a bucketload of cash for Warner Bros. It also helped that Stallone and Kurt Russell had insane chemistry onscreen that propelled the movie beyond being another generic buddy action comedy of its time.

Funnily enough, Stallone revealed to Fandango in 2019 that he continued to pitch Tango & Cash 2 to Russell, who had his reservations about the sequel. According to Sly, Russell told him, “I don’t know, Sly. There we were in our prime and now we’re in our unprime, I dunno.”

Demolition Man Sylvester Stallone Sandra Bullock
Image Credit: Warner Bros.

Out of all three movies, however, the biggest failure is not making Demolition Man 2. The 1993 movie ticked all the boxes of what Hollywood wants: good reviews, money, and franchise potential. Of course, there was talk of a sequel, but it never happened. In 2020, Stallone said there was work being done on Demolition Man 2, but it appears as though it went the way of the dinosaur – that, or the corporate musical chairs at Warner Bros. all but killed it.

In an industry that loves nothing more than milking the same idea until it turns into a decomposed corpse, it’s surprising that none of these three movies received sequels – even if they had happened without Stallone returning. Is it too late for them now, though? Perhaps. Both Rambo and Rocky moved on from Sly, so it’s likely that those movies will too. Expect reboots rather than sequels.

Of the three, at least one is easy to check off tonight: Demolition Man is currently streaming on Netflix.

Source: JustWatch
Tags: Action MoviesFeaturedSylvester Stallone
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About the Author: Sergio Pereira

Sergio is an entertainment journalist who has written about movies, television, video games, and comic books for over a decade and a half. Outside of journalism, he is an award-winning copywriter, screenwriter, and novelist. He holds a degree in media studies and psychology.

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