Sylvester Stallone is one of cinema’s biggest ever box office stars. While the majority of his films exist within the action genre, he has dabbled in comedy from time to time. As early as his breakout role in Rocky in 1976, the two-time Oscar nominee has flexed his ability to lighten the tone with subtle humour.
Now in his late 70s, Sylvester Stallone is moving away from action roles and consistently leaning more towards drama and comedy, with his hit TV series Tulsa King smoothly blending both genres. Although his comedic roles may be few and far between, he has proven he can really shine in a comedic setting. So, here’s our pick of his 5 best comedy roles in film and TV.
5. Stop! Or My Mom Will Shoot (1992)
Stop! Or My Mom Will Shoot was heavily slated by critics upon release and only managed to bring in $70.6 million worldwide, against a budget of $45 million. Stallone has been on record for some time saying that he deeply regrets the movie. Interestingly, he only starred in the film due to Arnold Schwarzenegger tricking him into believing he himself was gunning for the part. At the height of their bitter rivalry, Stallone took it upon himself to beat Arnie to the punch and made the movie himself. Although the flick has been widely regarded as Stallone’s worst ever role, over the years, it has garnered somewhat of a cult fanbase, with many classing it as a guilty pleasure of sorts.
What’s worth mentioning is the fact that this film never set out to win any awards – it set out to be a fun, family-friendly comedy with action sprinkled in. And it’s hard to say that it didn’t deliver. The plot is simple, it has its silly moments, and the action is somewhat lacking. However, Stallone has some hilarious moments that tap into the classic mother and son dynamic that most men can relate to. To that, on face value, Stop! Or My Mom Will Shoot is a rather fun movie and certainly boasts Stallone’s skills in comedy.
4. Grudge Match (2013)
Sylvester Stallone and Robert De Niro have an interesting history in cinema. The two actors competed for the Best Actor Oscar in 1977 for their roles in Rocky and Taxi Driver, respectively. Then in 1997, they shared the screen for the first time in the gritty crime drama, Cop Land. In 2013, they partnered up again, but for a comedy this time around.
Grudge Match tells the story of Henry Sharp (Stallone) and Billy McDonnen (De Niro), two retired boxers with a prolonged feud between them. Decades after their last fight, the two are coaxed out of retirement by slippery boxing promoter Dante Slate (played by Kevin Hart). With Billy more than keen to take on the fight, Henry is dubious but finds the spark again when he loses his job and becomes desperate for cash. Although the film was met with harsh reviews from critics, the chemistry between Stallone and De Niro is magnetic. De Niro plays the boisterous bruiser who has never really grown up, while Stallone plays the more straight-laced, grumpy opponent. Standing alongside comedy titan Kevin Hart, it is Stallone who really garners the laughs with his stern and understated rendition. While not a masterpiece, Grudge Match is a playful boxing comedy that offers a nostalgic feel as both men riff on their previous iconic boxer roles; Rocky for Stallone, and Raging Bull for De Niro.
3. Tango & Cash (1989)
By the late 80s, Sylvester Stallone had become one of the biggest action stars in the world thanks to his Rocky movies and the Rambo series. However, he had not yet capitalized on the popular buddy cop genre. So, in 1989, he sought to rectify that by teaming up with Kurt Russell in Tango & Cash. This cult action comedy follows the titular characters, a pair of mismatched cops, who must put aside their differences when they are framed by their ruthless arch-nemesis. As they are sent to prison, they now have to band together to go after the real criminals, with a lot of bickering along the way. Tango & Cash is a lighthearted action flick that is fully aware of what it is, blending over-the-top action with a back and forth dynamic between Stallone and Russell. In fact, Stallone likes the film so much that he has considered making a sequel or a revamp.
2. Oscar (1991)
In his early days in Hollywood, Sylvester Stallone struggled to land parts. As he divulged in his Netflix documentary Sly, he was even rejected for a background role in The Godfather. In 1991, he got his chance to rub it in the big wig’s faces when he was cast in the lead role of John Landis‘ gangster comedy, Oscar. At the time of its release, Stallone was one of the hottest stars in cinema and John Landis was one of the most revered filmmakers, so, many had high hopes for Oscar. However, it flopped at the box office, grossing only $23.5 million, against a budget of $35 million. But, as with many other Stallone movies, it achieved a second wind years later.
The plot centres on Angelo ‘Snaps’ Provolone (Stallone), a mobster who attempts to keep the promise he made to his dying father that he would give up his life of crime and go straight. However, things prove to be much more difficult than he imagined. With its inspiration drawing from popular screwball comedies of the 30s, Oscar has many slapstick moments whilst also holding an undertone of heart. The problem lies with the fact that many went into the movie expecting another action vehicle from Stallone, filled with gunfights, explosions, and piling body counts. All these years later, the critics may not be keen to go back on their harsh judgements, but audiences have grown to appreciate the film for Stallone’s comedic lead role and the stacked supporting cast.
1. Tulsa King (2022-Present)
Taylor Sheridan is one of the hardest-working figures in Hollywood. He is known for creating hit shows like Yellowstone, Mayor of Kingstown, and 1883, as well as writing movies like Wind River, Sicario, and Hell or High Water. With a penchant for darker material, when his TV series Tulsa King first landed in 2022, many expected more of the same. However, what they got was way more comedic, and this is largely due to Sylvester Stallone’s charismatic and cheeky performance.
Tulsa King follows Dwight Manfredi, a fast-talking New York City gangster who is exiled by his crew to Tulsa. Deciding to make the most out of a bad situation, Manfredi decides to fully take over the criminal underworld, wrangling together a crew of unlikely villains along the way. While sombre material is explored, and moments of violence explode, the show is carried with a playful tone that is rather lighthearted. There are many funny characters in the show, but it is Stallone who steals the show in his lead role. As a man who has spent 25 years in prison, he’s out of touch with the world, which makes for hilarious scenarios. His menacing presence is simmered by his constant “dad jokes” and lack of tact, almost like a gangster version of Larry David. This has clearly resonated with audiences as the show is now entering its third season, and Stallone is trending heavy again as a result.
Read Next: 5 Times Sylvester Stallone Deserved An Oscar
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