Rocky Versus Rambo: We Rank Sylvester Stallone’s Best Roles of All Time
Including when Sly went head-to-head with Robert De Niro!
Three-time Oscar nominee Sylvester Stallone, 76, takes the big leap to the small screen on Nov. 13 with his first TV role in Tulsa King, a new Paramount+ drama from Yellowstone creator Taylor Sheridan, 52. He’ll star as Dwight “The General” Manfredi, an Italian mafia capo who is exiled to Oklahoma after spending 25 years in prison; once there, he’s forced to get creative as he assembles a new criminal empire on the Great Plains. Before digging into the series, we’ve assembled a watchlist of his 10 greatest film roles — sound off below in the comments if we’ve left off any of your favorites!
10: Oscar (1991)
The premise: This modern twist on a 1930s screwball comedy by director John Landis, 72, sees Stallone in full comedy mode as Depression-era gangster Angelo “Snaps” Provolone, who promises his father on his deathbed that he’ll give up his life of crime. The underrated farce, which was originally supposed to star Al Pacino (82), was savaged by critics upon its release, but there’s plenty to love, including an opera-inspired score by Elmer Bernstein and a stacked supporting cast with such standouts as Kirk Douglas, Don Ameche, Chazz Palminteri (70) and Marisa Tomei (57) in one of her first roles. Stallone achieves a kind of cartoonish charisma that’s refreshingly unlike anything you’ll find in his standard action fare.
The best part: Dialectician Dr. Thornton Poole (Tim Curry, 76) tries to give Snaps elocution lessons with memorably disastrous results.
Watch it: Oscar on Prime Video, Apple TV
9: Death Race 2000 (1975)
The premise: This bloody cult classic is not for the faint of heart. It’s the year 2000, and the United States is a failing totalitarian regime under martial law. To distract and entertain its citizens, the government has created the Transcontinental Road Race, in which drivers speed across the country — mowing down innocent pedestrians for bonus points. Stallone stars as racer Machine Gun Joe Viterbo, a Chicago gangster who carries a Tommy gun, and though this film is far from great art, it encapsulates all the campy, mindless fun you’d want from a Roger Corman–produced exploitation flick.
The best part: A Stallone line for the ages: “You know, Myra, some people might think you’re cute. But me, I think you’re one very large baked potato.”
Watch it: Death Race 2000 on Apple TV, Tubi
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8. The Suicide Squad (2021)
The premise: Sly’s face is never seen, but he still makes a big impact in this DC Comics sequel about a group of supervillains who are assembled by intelligence officer Amanda Waller (Viola Davis, 57) and sent on a secret suicide mission to a South American island that houses a Nazi-era research facility. Stallone voices the fan-favorite Nanaue/King Shark, a half-man, half-shark hybrid who’s at once a ruthless killer who can tear his enemies in half and a lonely goofball just trying to make friends. He plays the role with a sense of childlike wonder that makes this man-eater surprisingly endearing and, dare we say, adorable.
The best part: In one cute scene, King Shark tries to make friends with an aquarium full of fish, though it doesn’t go as planned.
Watch it: The Suicide Squad on Prime Video, Apple TV, HBO Max, Hulu
7: Cliffhanger (1993)
The premise: In this stunt-filled thriller, a group of criminals led by Eric Qualen (John Lithgow, 77) botches the hijacking of a U.S. Treasury plane, leaving them — and $100 million — stranded in the Rockies. Their distress call is answered by the skilled mountain climber Gabe Walker (Stallone), who’s dealing with his own trauma after watching a friend fall to her death during a failed rescue attempt. The film was nominated for three Oscars, and its high-octane action set pieces included a $1 million stunt that was listed in Guinness World Records as the costliest aerial stunt ever performed. Need another reason to be impressed? Stallone overcame a lifelong fear of heights to film in Italy’s Dolomites, and he told director Renny Harlin before filming, “The highest I will ever go is the heels of my cowboy boots.”
The best part: The climactic fight scene between Stallone and Lithgow involves a helicopter, a steel rope ladder and plenty of — you guessed it — hanging from cliffs.
Watch it: Cliffhanger on Prime Video, Apple TV, Hulu
6. Demolition Man (1993)
The premise: Known for the collateral damage he causes, LAPD Sgt. John Spartan (Stallone) — a.k.a. “The Demolition Man” — bungles a rescue attempt when psychopathic criminal Simon Phoenix (Wesley Snipes, 60) kidnaps a busload of hostages. Both cop and crook are sentenced to be cryogenically frozen, and when Phoenix is thawed out for a parole hearing in 2032, he escapes and begins wreaking havoc on San Angeles, a utopian megalopolis in Southern California. Lt. Lenina Huxley (Sandra Bullock, 58) knows that the only hope is to defrost Spartan and see if his old war with Phoenix will, uh, heat up once again, and the result is a surprisingly funny blend of satire and shoot-em-up.
The best part: Stallone is clearly having a hell of a good time with one-liners such as “You’re gonna regret this the rest of your life … both seconds of it.”
Watch it: Demolition Man on Prime Video, Apple TV
5: Nighthawks (1981)
The premise: Originally planned as The French Connection III, the reworked thriller — Stallone’s first major action film — follows two NYPD sergeants, Deke DaSilva (Stallone) and Matthew Fox (Billy Dee Williams, 85) as they try to track down a deadly European terrorist named Wulfgar (Rutger Hauer) who’s intent on causing chaos in the city. What ensues is a high-stakes cat-and-mouse game through the Big Apple that sees them dashing around everywhere from subway platforms to discos to the Roosevelt Island Tram. Stallone dials it back for this underrated gem, which Janet Maslin of The New York Times summed up as “clumsy but fast, and very vividly etched, with plenty of excitement and spark.”
The best part: The subway chase scene is a tense and well-choreographed thing of beauty.
Watch it: Nighthawks on Prime Video, Apple TV
4: Cop Land (1997)
The premise: Stallone holds his own opposite acting legends Robert De Niro (79), Harvey Keitel (83) and Ray Liotta in this “urban Western” from Walk the Line director James Mangold (58). He packed on 41 pounds to play Freddy Heflin, a schlubby New Jersey sheriff who has long admired the NYPD but can’t join their ranks because he’s half-deaf after nearly drowning. His town of Garrison is populated by crooked New York City cops with mob connections, and when one of them is involved in a racially motivated shooting, Heflin makes the tough decision to investigate the men he previously idolized.
The best part: For a taste of Stallone’s underrated acting prowess, check out the scene in which he goes head-to-head with De Niro’s Internal Affairs agent as he begs for help on the case.
Watch it: Cop Land on Prime Video, Apple TV, HBO Max, Hulu
3: First Blood (1982)
The premise: This 1982 film introduced the world to Stallone’s second big franchise hero, John Rambo, a veteran with impressive fighting skills who’s left traumatized by his time in Vietnam. In the first installment, Rambo travels to Hope, Washington, to see an old military buddy, who he learns died from Agent Orange–induced cancer. Upon Rambo’s arrival, the sheriff (Brian Dennehy) harasses him for being a drifter and kicks him out of town. Rambo snaps and heads for the hills, where he reverts to the brutal guerrilla tactics he learned overseas in his escalating battle with the authorities. In future films, the elite fighting machine headed to Vietnam, Afghanistan, Burma and Mexico on deadly missions.
The best part: Though First Blood is rightfully remembered for its brutal action sequences, Stallone is at his most effective in an emotional breakdown scene that sees him melting into a puddle of tears and recounting his terrible experiences during the war and the awful ways he’s been treated since coming home to America.
Watch it: First Blood on Prime Video, Apple TV, HBO Max, Hulu
2: Rocky (1976)
The premise: When Stallone wasn’t getting the acting roles he wanted in the mid-1970s, he took matters into his own hands and created one of the most indelible characters in film history: underdog Philly boxer Rocky Balboa, whom the American Film Institute ranked seventh on its list of the 50 greatest heroes in American cinema history. Costarring Talia Shire (76) as Rocky’s girlfriend, Adrian; Burgess Meredith as his trainer Mickey; and Carl Weathers (74) as his rival Apollo Creed, the film was a sleeper hit that went on to become the highest-grossing film of 1976 and a three-time Academy Award winner, including for best picture. It also kicked off a decades-spanning franchise that has taken in more than $1.7 billion at the global box office and counting.
The best part: There are perhaps more iconic scenes (those museum stairs!), but the film reaches its emotional peak when Rocky and Adrian finally profess their love for one another after his bout with Creed.
Watch it: Rocky on Prime Video, Apple TV
1: Creed (2015)
The premise: OK, we know this might sound blasphemous to Rocky diehards, but Stallone bested even his stellar debut in this heartfelt reboot from director Ryan Coogler. Balboa returns to train and mentor Adonis Creed (Michael B. Jordan), the son of his former rival Apollo, but the elder boxer has to battle a life-or-death fight of his own when he’s diagnosed with non-Hodgkin’s lymphoma. The role saw Stallone at his most vulnerable and introspective, and he was rewarded with best supporting actor wins from the National Board of Review Awards, the Critics’ Choice Awards and the Golden Globes, plus his first Oscar nomination since 1977. It’s a full-circle moment that combines decades of nostalgia with flat-out great acting.
The best part: Try not to get choked up when Adonis and a visibly frail Rocky ascend the Philadelphia Museum of Art staircase and Rocky quips, “I think they added a few more steps.”
Watch it: Creed on Prime Video, Apple TV
Nicholas DeRenzo is a contributing writer who covers entertainment and travel. Previously he was executive editor of United Airlines’ Hemispheres magazine and his work has appeared in the New York Times, Conde Nast Traveler, Travel & Leisure, Sunset and New York magazine.