Sylvester Stallone’s illustrious career, spanning nearly six decades, has largely been defined by his two highest-grossing franchises, Rambo and Rocky. Sly holds the record for having a number 1 movie in Hollywood for six consecutive decades, something no one else has ever accomplished. However, behind his coveted movie posters are a record 40 Razzie nominations, and not all of them are totally unjustified. From roles he accepted without reading the source material to those where he was completely miscast, Sylvester Stallone has no shortage of bad films.
The best thing about Stallone ,though, is his ready acceptance of his flaws as much as his wins and these are the biggest flops for which he has publicly expressed regret.
7D-Tox (Eye See You) (2002)
This is the closest that Stallone has come to starring in a horror film, although, like his other early 2000s films, it went right down the drain. He plays Jake Malloy, an FBI agent struggling with alcoholism after a haunting case, who signs up to a rehabilitation center for law enforcement officers in rural Wyoming. After a blizzard cuts off the rehab from the rest of the world, a serial killer starts killing the residents, forcing Malloy to go on the hunt once more. The film never really takes off despite its impressive start, with most of the scenes feeling obvious and the attempts at jump scares feeling forced.
It became one of Hollywood’s greatest ever Box Office flops netting less than $10 million at the Global Box Office on a $65 million budget. “It was funny, when we were met at the airport by the teamsters they’d have a sign in front of them saying DETOX, and all these actors like Kris Kristofferson, Tom Berenger and myself looked like we were going into rehab rather than a film shoot” Stallone told AICN while describing the many issues that bedeviled the film. He named it among the list of films he regrets.
6Driven (2001)
In a bid to diversify into sports racing, Sly wrote, produced and starred in this film which didn’t live up to expectations. In the film, he plays Joe Tanto, a retired car-racing driver who is forced out of retirement by his former boss to mentor the current champion who is struggling. Despite having a seasoned director in Renny Harlin, a star-studded cast and a hefty budget, the film was a huge commercial flop earning just $32 million domestically against an estimated $94 million budget.
In his interviews during production, Stallone said he was eyeing the huge international base of car racing fans, but that too flopped as the film made less than $25 million internationally. He later named Driven among his films that “went right down the toilet” saying that just like the main character Jimmy, he realized that you can’t always be number 1. Although Stallone’s performance was average, at best, lack of a proper storyline is what really ruined the film. Most of the scenes don’t sync as the plot seems to jump from one scene to another without really solving the conflicts. Eventually, Driven became a costly mistake that Stallone probably still regrets.
5Get Carter (2000)
This is one of Stallone’s biggest Box Office bombs, having made less than a third of its $64 million budget at the global Box Office. The film is a remake of a 1971 British action thriller by Mike Hodges starring Michael Caine. In Stallone’s Get Carter, Stallone portrays Jack Carter, the Las Vegas based enforcer for the mob, who starts investigating the murder of his brother Ritchie which was framed to look like a DUI accident. Stallone’s charm as the no-nonsense Mafia boss turned investigator is admirable although the film’s tone is flat and the plot predictable.
This film pretty much marked the start of the decline of Stallone’s career in the 2000s. While Speaking to THR, Stallone bemoaned Get Carter as the most underrated film of his career. “I think Get Carter was really underrated. That was a big disappointment. I learned the hard way that [remakes], even if you do it better than the original, there’s a tremendous nostalgia attached to the original,” he said back in 2022. It is one of the rare instances where a Stallone action film failed so badly at the Box Office.
4Oscar (1991)
This was another attempt by Stallone to diversify into comedy that didn’t go according to plan. It was a remake of a 1967 French film of the same name in which Stallone plays a mafia boss, Angelo Provolone known by his street name, Snaps. Unlike the French film, Stallone’s Oscar is set in 1930s New York during the Depression. Despite Stallone shining at the Italian accent, nothing about his performance brings out Snaps’s intended humorous personality. Critics panned the film leading to horrible scores on every rating platform including opening at just 4% on RT. It was also a commercial disaster, only managing to return just over half of its $35million budget at the Box Office.
Having a polished script and an excellent director in John Landis didn’t help the film’s comedic prospects. Stallone looks like he would rather be somewhere else throughout the film. There is also zero chemistry between the cast as all intended action and slapstick comedy fall flat. Surprisingly, Stallone was selected for the role by Landis himself, but it was clearly a big mismatch. In his Netflix documentary ‘Sly’ Stallone dismissed Oscar as one of his career mistakes during the low period of his career when he wasn’t making Rambo and Rocky.
3Rhinestone (1984)
At the peak of his career as an action film star, Stallone attempted to diversify into a musical comedy by teaming up with Dolly Parton. In the film, Parton plays renowned country music singer Jake Farris who makes a bet with her obnoxious and sexually abusive boss, Freddie, to turn anyone he chooses into a country music star in exchange for the termination of her oppressive contract. To make her job difficult, Freddie picks an NYC cabbie with zero talent and style called Nick Martinelli (Stallone). Clearly, the film was a flop earning just $21 million at the Box Office on a $28 million budget.
While Parton succeeds in her job in the film, and two even have some resemblance of chemistry, nothing about Stallone’s appearance remotely spells country music star both at the beginning and at the end. Stallone, rigid and bulked up from playing Rambo first blood, appears out of touch with the script and looks like he would rather punch his way through the guitar rather than play it. While expressing his regret for Rhinestone, Stallone said he would have done many things differently. On her part, Dolly Parton said the world wasn’t ready to see Stallone as a musician.
2Judge Dredd (1995)
Judge Dredd was set to be Sylvester Stallone’s Terminator when he signed up to play the hard as nails street judge Joseph Dredd. The film is set in a post-apocalyptic 22nd century where most of humanity subsists alongside robots and clones in overcrowded Mega Cities overrun with crime. Dredd and his fellow judges play judge, jury and executioner, delivering instant justice on the many criminals. In Stallone’s case, his character is framed for murder, leading to him having to fight to clear his name while also saving the city from his archnemesis, Rico, a criminal backed by a powerful army of clones and robots.
Despite having a meaty storyline and strong financial backing, the film never lived up to the high expectations. Stallone signed up for the role without even reading the books on which it was based. While the role wasn’t a mismatch, a more humerous version of Stallone would have made the film better. Stallone called the film “the worst mistake he ever made” during a 2010 interview, saying he and his team could have handled the script better. Judge Dredd represents another win by Schwarzenegger over Stallone since the former was first offered the role but turned it down.
1Stop Or My Mom Will Shoot (1992)
Arnold Schwarzenneger was first offered the lead role of Joseph Bomowski, a detective whose mother comes to town and starts interfering in his life including his cases. After reading the script and realizing it was bad, he faked interest in the role to lure his industry rival Sylvester Stallone into going for it. Stallone eventually landed the career-ruining role because the script didn’t give the lead actors much to go with. Stallone and Estelle Getty who played Bomowski’s mom still put in their best efforts, but the flat jokes and barren plot left little to desire from the film.
Stop Or My Mom Will Shoot wasn’t as big a flop as the other films in the list, earning over $70 million globally, although it was still under its bloated budget. The critics still panned the film, giving it a 14% RT score. The film became a nightmare for Stallone as it earned him a record ninth consecutive Razzie nomination. Stallone condemned the terrible script during an interview in 2006 saying it was probably the worst film he’s ever starred in.
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Conclusion
The immense success of Stallone’s long career often overshadows the many lows he has experienced. In his attempt to diversify from action to other genres, Stallone tried out lots of other roles, most of which turned out badly. Eventually, he has proved his ability to diversify with his now-acclaimed TV debut as Dwight Manfredi in Taylor Sheridan’s Tulsa King. However, he has also acknowledged the films he regrets as this list outlines.
Written by Billy Oduory
