A Hollywood mainstay since the mid-70s, Sylvester Stallone has seen several setbacks and resurgences throughout his storied career. His latest phase, anchored by his enormously entertaining turn in the Paramount+ series Tulsa King, includes the new Netflix documentary Sly, which had its world premiere at the Toronto International Film Festival back in September. In honor of the film, releasing on November 3, check out the essential Sylvester Stallone films – the best, the worst, and the most important to his story.
At the end of his rope after getting turned down even for background work, Stallone did what every struggling actor wishes they could do: He wrote himself a career-defining role and earned two Oscar nominations.
Continuing through five more films and inspiring an off-shoot trilogy, Rocky has become one of the defining American film franchises, something neither Stallone nor any of his filmmaking partners at the time could have guessed. The filmmaking reflects that scrappy, unassuming, give-it-everything-you’ve-got attitude Stallone had when he wrote it, giving audiences one of the most rewarding underdog stories of all time and setting the stage for the next five decades of Stallone’s career. Of all his work, call this the most definitive of Sylvester Stallone films.
Paradise Alley (1978)
After Rocky, Stallone had Hollywood on the ropes, able to do just about anything he wanted. He wanted to direct a script he had written before Rocky about three Italian-American brothers who got involved in professional wrestling in the 1940s. The experience proved to be formative in more ways than one, as Stallone not only got his first taste of directing himself in his own script but learned important lessons about how to deal with studio demands.
In a 1980 interview with Roger Ebert, he said that he would “never forgive myself for the way I allowed myself to be manipulated during the editing of that film,” stating that he was unhappy with the way it turned out. Negatively compared to Rocky by both critics and audiences alike, Paradise Alley only just barely made back its $6M budget at the box office.
Instead of the starring role in Robert Zemeckis’s Romancing The Stone, Stallone took $5M and a percentage of the gross to star in Rhinestone, a Dolly Parton vehicle about an experienced country singer attempting to turn a Manhattan cabbie into a country music star. It ended up as his first film to not make back its budget. A legendary flop, the film was a behind-the-scenes disaster from the beginning: Studio execs allowed CAA to convince them that Stallone was the only male star right for the part who could stand up to Parton’s star power (CAA represented them both), and while that may have been true, the problems he caused the production were legion.
Allowed to serve as the film’s director without actually taking the title (and without the knowledge of director Don Zimmerman, whom Bob Clark later replaced), and allowed to completely rewrite the screenplay without any input from original screenwriter Phil Alden Robinson, by all accounts, Stallone made the film far different and far worse than initially conceived. Stallone has said that he regretted making the film but that working with Parton was the most fun he ever had on a movie.
Rambo: First Blood Part II/Rocky IV (1985)
In 1985, Stallone had one of those years that define a star for their entire career. First, in May, came the sequel to 1982’s First Blood, making John Rambo one of the most iconic figures of 1980s cinema. Then, six months later, the third Rocky sequel was released, seeing Stallone square off against Dolph Lundgren as evil Russian Ivan Drago.
Each film set records, with Rambo as the first film released on over 2,000 screens domestically and Rocky IV getting an expansion in its fourth week in theaters to 2,232 screens, the widest domestic release ever at the time. Rambo’s opening weekend set a record at the UK box office, which Rocky IV broke months later. This one-two punch of franchise Sylvester Stallone films cemented his star status, elevating him from superstar to bona fide legend.
This cop-actioner may not be the most beloved of Sylvester Stallone films, but its importance to his career cannot be understated. On the same day as its domestic release, Stallone announced in a press conference his new six-year, ten-picture domestic distribution deal with United Artists, including the formation of his own production company, White Eagle Enterprises. Carolco Pictures would handle international distribution as part of the deal.
The lucrative deal seemed like the logical next step after Stallone’s box office triumph in 1985, but in a cruel twist of fate, the deal produced only one film (1989’s Lock Up), signaling the start of a disappointing run of flops for the star. White Eagle Enterprises eventually got absorbed into Carolco.
Over the Top (1987)
Reviled by critics at the time, Over The Top has since become one of Stallone’s most iconic films. Emblematic of a specific brand of ‘80s cinematic cheese, this story of a truck driver entering an arm wrestling competition to provide a better life for his son struck many as taking its title too much to heart. Over The Top goes blissfully over the top; sentimental in a way that only ‘80s action films could get away with.
One could make the case that this brand of films just repackaged the melodrama of 1950s “women’s pictures” in the ultra-masculine clothing of the 1980s, centering their lead’s love for their families and showing them go through a physical gauntlet, as opposed to an emotional one, in order to keep them safe. Countless examples of films like this litter the 1980s, but most don’t have an actor of Stallone’s caliber or a Giorgio Moroder score to keep them as entertaining as Over The Top.
Stop! Or My Mom Will Shoot (1992)
The battle between Stallone and Arnold Schwarzenegger for action box office supremacy captured Hollywood headlines through most of the 1980s. The two biggest action stars in the world went back and forth for years before the Austrian Oak decided to engage in some psychological warfare.
Knowing that the screenplay for Stop! Or My Mom Will Shoot was a dud, Schwarzenegger feigned interest in the film and let the rumor mill start spinning. Schwarzenegger’s interest was all Stallone needed to want to do it himself. While the film did well enough at the box office, thanks to the combined star power of Sly and The Golden Girls star Estelle Getty, it received terrible reviews, the worst of Stallone’s career up to that point. Stallone has repeatedly cited it as the film he most wishes he hadn’t made.
After the back-to-back critical drubbing Stallone took on Stop! Or My Mom Will Shoot and the previous year’s Oscar – not to mention Rocky V, a series low point both critically and commercially – Stallone needed a comeback vehicle. He got it in Renny Harlin’s Cliffhanger, which opened out of competition at the Cannes Film Festival and returned Sly to the top of the box office charts.
A good thing it did, too, as the film had gone so severely over budget that production had to shut down twice because production company Carolco couldn’t afford to pay the crew. Still, the film signaled that Stallone still had what it took to open a film, and his second 1993 release, Demolition Man, also found box office success.
Judge Dredd (1995)
Unfortunately, Stallone’s next mega-budget starring vehicle became a major flop. A $90M hard-R comic book adaptation, Judge Dredd submitted five separate cuts to the MPAA to avoid an NC-17 rating, and what survived pleased neither critics nor fans of the comic. While the production design and visual effects looked spectacular for the time, the story confused many, and the performances couldn’t save it.
During production, Stallone demanded rewrites to fit his idea of comedy better, apparently not realizing the writers’ intent to make a pitch-black satire instead of a broad comedy. All the drama resulted in a film so tonally disjointed that even Stallone’s committed performance couldn’t hold it together.
Cop Land (1997)
After years as a highly-muscled action hero, Stallone decided to return to the mid-budget adult dramas with which he began his career and court some prestige in the process. Working with then-up-and-coming writer-director James Mangold on the neo-noir crime drama Cop Land, the Italian Stallion gained 40 pounds to portray the run-down sheriff of a New Jersey town, in over his head with some bad cops. The film garnered him favorable reviews and did well at the box office, but Stallone has since expressed his belief that the film’s non-blockbuster-level grosses contributed to the perception of him as a star past his prime.
The Expendables (2010)
In the mid-00s, Stallone revisited his most iconic characters – Rocky and Rambo – in decades-later sequels that did well at the box office but not up to the level of previous films in the franchises. But in a strange twist, neither of those films completely restored his star power. That honor went to The Expendables, the first entirely original film Stallone had both written and directed since the beginning of his career.
Gathering a murderer’s row of action superstars (Jet Li, Dolph Lundgren, Mickey Rourke, Jason Statham, Bruce Willis) and sports stars (Steve Austin, Randy Couture, Terry Crews) to portray a group of elite mercenaries in an homage to the rock ‘em-sock ‘em action films of the ‘80s was a stroke of genius, and Stallone received the biggest opening weekend of his career, not to mention a third successful franchise, as a reward.
Everything eventually comes full circle. Despite 2006’s Rocky Balboa being considered by all as the end of the Rocky franchise, MGM hired Ryan Coogler to write a spinoff. That spinoff, focused on Apollo Creed’s son Adonis (Michael B. Jordan), ended up bringing Rocky back. The film gave Stallone his best material in ages, and the actor responded with one of his best performances, garnering plaudits from critics and an Oscar nomination and Golden Globe win for Best Supporting Actor. The film and the two subsequent sequels served as the launchpad for Stallone’s latest resurgence, with the Taylor Sheridan-penned Tulsa King and the reality series The Family Stallone.