Sylvester Stallone is the rare actor to have held two iconic roles in long-running franchises. Between playing boxer Rocky Balboa in eight Rocky and Creed movies and Vietnam veteran John Rambo in five Rambo movies, starring in The Expendables franchise, and playing the title characters in one-off movies like Judge Dredd, Tango & Cash, Demolition Man, and Cobra, he could hardly be more of a big-screen legend.
However, he turned down the opportunity to play quite a few more roles that later proved to be similarly iconic. The following five characters could have been added to the star’s already extensive filmography had he made different decisions.
Jack Colton in Romancing the Stone (1984)

Shortly after the release of First Blood, which kicked off the Rambo franchise, Sylvester Stallone was faced with a choice between two stones. On the one hand, he could star in Robert Zemeckis’ Romancing the Stone as Jack Colton, the Indiana Jones-esque adventurer who accompanies a sheltered romance author (Kathleen Turner) on a dangerous rescue mission in the Colombian jungle. On the other hand, he could star in Bob Clark’s Rhinestone as Nick Martinelli, a New York City cab driver who gets a makeover as a country star from singer country singer Jake Farris (Dolly Parton), who is taking on this challenge to win a bet and get out of her contract.
He ultimately chose Rhinestone, a critically reviled flop that went on to gross $21.4 million against its $28 million budget. Such is life. Meanwhile, Romancing the Stone became the eighth highest-grossing movie of 1984 worldwide and spawned the 1985 sequel The Jewel of the Nile. Although other actors were considered for the role, including Paul Newman and Christopher Reeve, the role went to Michael Douglas, who was already a producer on the project.
John McClane in Die Hard (1988)

When Hollywood got the ball rolling on an adaptation of the 1979 Roderick Thorp novel Nothing Lasts Forever (which they retitled as Die Hard), they reached out to some of the biggest stars in 1980s action cinema to play the charismatic lead. That would be NYPD cop John McClane, who finds himself in the middle of a terrorist situation when visiting his estranged wife (Bonnie Bedelia) in Los Angeles. First they were contractually obligated to offer the role to Frank Sinatra. He declined, possibly on account of his being 70 years old at the time. Arnold Schwarzenegger also turned down the role. So did Clint Eastwood, Mel Gibson, and Burt Reynolds. And so did (guess who) Sylvester Stallone.
So did Bruce Willis, come to think of it. He originally couldn’t work the movie into his schedule alongside the sitcom Moonlighting, but when his co-star Cybill Shepherd got pregnant and production was delayed, he officially signed on to play John McClane. The result was Willis instantly transforming from sitcom star to action hero and going on to star in four sequels. Altogether, the Die Hard movies have grossed more than $1.4 billion, making it the ninth highest-grossing action franchise of all time, below Rocky ($1.9 billion) but considerably above Rambo ($818.9 million).
Detective David Mills in Se7en (1995)

Another major role that Stallone turned down was Detective David Mills in David Fincher’s breakthrough feature Se7en. Mills, who is the lead of the serial killer thriller, is a homicide detective on the hunt for a murderer who commits killings inspired by the seven deadly sins. The role (which Denzel Washington also turned down) ultimately went to Brad Pitt, who had previously held notable roles in Thelma & Louise and Interview with the Vampire.
The movie ultimately became the biggest movie of the year at the global box office (outgrossing Toy Story) and put David Fincher on the map. He would later collaborate with Brad Pitt again on the 1999 classic Fight Club. While Stallone has never specified his reasons for turning down the role, he later listed Se7en as one of “several films I missed out on and wished I’d done” during an Ain’t It Cool News Q&A.
Louis Gara in Jackie Brown (1997)

During an interview with the Canadian magazine Maclean’s, Stallone confirmed that he turned down the role of Louis Gara in Quentin Tarantino’s Jackie Brown. The character, who is an ex-convict, is the secondary antagonist in the story, which follows the titular flight attendant (Pam Grier) finding herself in a no-win situation when smuggled money puts her at the center of a stand-off between an arms dealer (Samuel L. Jackson) and law enforcement.
While Stallone didn’t reveal the reason why he turned down that particular role, which was Tarantino’s first directorial feature after the zeitgeist-defining smash hit Pulp Fiction, a different major star had no compunctions about hopping on the Tarantino train. The role eventually went to two-time Oscar winner Robert De Niro.
Stuntman Mike in Death Proof (2007)

As it turns out, Jackie Brown wasn’t the only Quentin Tarantino role that Stallone turned down. After choosing not to play Louis Gara in Jackie Brown, he was offered the role of Stuntman Mike in Death Proof, which was Tarantino’s contribution to the throwback double feature event Grindhouse, in which it was paired with Robert Rodriguez’s Planet Terror. Stuntman Mike, who is a Hollywood stuntman who uses his tricked-out car to murder unsuspecting women, would have been an even bigger role for Stallone, as he is the primary antagonist of the movie.
However, Stallone took issue with the character’s M.O. He told Maclean’s that “I said, ‘There’s no way. I have two daughters, and this fellow, his hobby is putting teenagers in his car and smashing them into a wall. That’s not going to work.’” The role eventually went to Kurt Russell, who would go on to appear in two more Tarantino movies, namely The Hateful Eight and Once Upon a Time… in Hollywood. Stallone, on the other hand, has still never starred in a Tarantino movie.
There are also a number of huge roles that Sylvester Stallone was considered for but didn’t get, rather than turning them down. This includes Han Solo in 1977’s Star Wars (the iconic role put Harrison Ford on the map), Superman in 1978’s Superman (which eventually went to Christopher Reeve), Axel Foley in 1984’s Beverly Hills Cop (he was actually cast in the role, but his rewrite of the script upped the budget so much that producers reverted to the original script and brought in Eddie Murphy to play the lead), Eddie Valiant in Who Framed Roger Rabbit (the role went to Bob Hoskins), and Mr. Freeze in 1997’s Batman & Robin (the role was eventually played by Arnold Schwarzenegger).
He was also considered, alongside Schwarzenegger, for the 1997 action two-hander Face/Off, in one of the two roles that ultimately went to Nicolas Cage and John Travolta.
So which of these roles would you most like to have seen Sylvester Stallone play once upon a time? Sound off in the comments below!