Every Sylvester Stallone Movie of the 1990s, Ranked

The 1990s was a particularly illustrious decade for action movies. And the one man that stood above the rest was Sylvester Stallone. Having already established himself as one of the toughest tough guys out there with the Rocky and Rambo franchises in the 1970s and the 1980s, it was time for Stallone to dominate the following decade with more epic hits.

Of course, the actor avoided being typecast in the 1990s and dared to explore diverse genres, bring a raw and physical style of acting, and strike a chord with fans through a more grounded and emotional portrayal of characters. The decade saw Stallone flex the attributes that made him famous while also pushing the limits of his own talents. There was fierce competition at the box office, but he managed to thrive under pressure.

From the stylized violence of Demolition Man to the all-out mayhem of The Specialist, Stallone dominated the decade through 11 movies across genres like action, thriller, comedy, and sci-fi. Here is a ranking of Sylvester Stallone’s movies from the 1990s.

11 Stop! Or My Mom Will Shoot (1992)

A buddy comedy directed by Roger Spottiswoode, Stop! Or My Mom Will Shoot pairs Sylvester Stallone with Estelle Getty. The former plays a tough-as-nails LAPD cop named Joseph Bomowski and the latter plays his frail and overbearing mother, Tutti. What starts as a routine visit from Tutti spirals into chaos when she progressively interferes in Joe’s life and accidentally gets involved in her son’s cases.

A Family Comedy That Tries Too Hard

Stop! Or My Mom Will Shoot was not a hit among critics, who gave it half a star and called it “numbingly awful” and “100% predictable.” It was meant to stand out, what with the unique collaboration between Stallone and Getty as the mother-son duo, but instead, the movie feels flat and unfunny. Certain scenes, including one where Tutti helps someone get off a tall building using a bullhorn, are not as humorous. Regardless, it is one of the few times Stallone has headlined a full-on comedy, and for that, it deserves some love.

10 The Specialist (1994)

The Specialist is an action thriller revolving around Ray Quick, a former CIA explosives expert who had to resign after an incident and he became a professional hitman after. Ray is hired by a mysterious woman named May Munro who seeks revenge against the men who murdered her family. As Ray analyzes the case, he discovers more people from his past, including his former partner Ned Trent, are involved and they seek to bring him out of hiding to settle a score.

An Explosive Thriller Worth Revisiting

Set against the backdrop of Miami’s gritty underworld, The Specialist may not be as wild as others in the action/romance genre, but it is quite explosive and steamy. Director Luis Llosa ratchets up the suspense with a meticulously planned game of cat and mouse between Stallone’s Ray and James Woods’ Ned. They walk the treacherous line of being the hunter and the hunted, which provides a great dynamic. Speaking of dynamics, Stallone shares a brilliant one with Sharon Stone, who plays May.

9 Assassins (1995)

Stallone emerges in his true form in Assassins, where he plays Robert Ruth, a top-tier hitman preparing to exit the profession after one final mission – to kill a computer hacker named Electra and four Dutch buyers. However, his plans are thwarted when an ambitious assassin and rival named Miguel Bain eliminates his targets and openly declares a challenge. What follows is high-stakes action and an edge-of-your-seat confrontation.

Sylvester Stallone vs. Antonio Banderas

Assassins is anchored by Stallone’s familiar charm and grit, which he portrays perfectly well through his complex and conflicted character. He goes toe-to-toe with Antonio Banderas’ Miguel, a young and enigmatic but unhinged assassin looking to take Rath’s place. The movie is known for its incredible action sequences, electrifying performances, and the globe-trotting assassin premise that seems to always work on diehard fans of the genre.

8 Judge Dredd (1995)

Few actors were as successful in action movies as Stallone in the 1990s. And the fact that his films married the genre with others like comedy and sci-fi is even more fascinating. Judge Dredd, which takes place in a dystopian future where America has become a wasteland and crime is routine in the cities, sees Stallone take on the role of the iconic comic book character. As the titular Judge Dredd, after he’s framed for a crime he did not commit, he must clear his name and uncover a conspiracy.

A Sci-Fi Epic Based On a Comic Book

Sylvester Stallone dives right into the stern and commanding role of Judge Dredd. He showcases his skills with both an intimidating presence and flashes of dark humor befitting his character. The movie, directed by Danny Cannon, is a visually striking piece of work that brings Stuart Urban’s graphic novel to life in a way that fascinates and engages the audiences. The special effects and the design were true-to-source, but the movie deviates from the core story. Still, its bold vision and Stallone’s acting make it a standout in the ’90s.

7 Daylight (1996)

Rob Cohen’s disaster drama, Daylight, was received with frowns by critics, but it managed to recoup double its production budget at the box office. Its plot goes something like this: in upstate New York, when a catastrophic explosion drives people to hole up in the Holland Tunnel beneath the Hudson River, it is up to disgraced EMT worker Kit Latura to come out of his current job as a taxi driver and lead the rescue effort. He uses his skills and expertise to help evacuate all stranded survivors in a race-against-time situation.

Stallone Leads a Life-Or-Death Rescue Mission

Cohen, known for lending a hand in directing and producing some of the best high-profile movies, excels in creating suspense and tension in this disaster drama. With each close call inside the tunnel, we are provided with an excellent blend of action and heartfelt moments. Stallone, obviously, portrays Latura perfectly. He’s both strong and vulnerable in the face of seemingly impossible odds, which is what the actor does best.

6 Rocky V (1990)

The sequel to Rocky IV and overall, the fifth entry in the franchise, Rocky V brings Sylvester Stallone back on the big screen to play Rocky Balboa. Dealing with head injuries from his last fight and facing financial ruin because of some faults made by his accountant, Rocky is barely making ends meet. When the opportunity to train a new protégé, Tommy Gunn, arises, Rocky reluctantly agrees. But as he becomes deeply invested in Tommy’s success, his relationship with his son suffers.

Stallone’s Most Emotional Rocky Movie

Rocky V is considered the worst movie in the franchise. It disappointed fans and critics at the time. But what’s interesting is that the movie contains Stallone’s most emotionally grounded and raw performance as it takes a deep and introspective dive into Rocky’s life. Gone are the glory days and the glamor of victory; he is now a broken man and former champion learning that there is more to life than just fighting. John G. Avildsen’s direction is layered and tense and he makes sure Rocky V reminds fans why Stallone is forever linked to the character.

5 Oscar (1991)

In Oscar, Sylvester Stallone stars as Angelo “Snaps” Provolone, a mobster in the 1930s, who makes a promise to his dying father – that he will leave his life of crime behind and become an honest businessman. As he tries to honor this wish, Provolone finds himself turning his trusted right men into associates and getting entangled in a series of mishaps and misunderstandings involving his daughter, his accountant (who is in love with his daughter), and several other characters.

Stallone In a Rare Comedic Role

A change of pace for Stallone, Oscar sees the actor depart from his usual action-packed roles and allows him to present his comedic chops and versatility in acting. Playing the mobster-turned-businessman made way for endless situations where Stallone could shine. The rapid-fire dialogue and absurd humor pay homage to classic screwball comedies. Oscar is directed by John Landis and it is an entertaining fish-out-of-water story that also stars Marisa Tomei, Tim Curry, and Chazz Palminteri.

4 Cliffhanger (1993)

A clever take on the word, especially in the movie industry context, Cliffhanger is an action-packed and mildly humorous thriller that centers around Gabe Walker, a mountain rescue ranger trying desperately to move on from his tragic life and settle into a new life. But his quiet existence is shaken when a group of thieves crash-land in the Rockies with a stolen fortune worth over $100 million in three suitcases of uncirculated bills. Walker gets pulled into action to save the hostages and battle the criminals.

Cliffhanger Was Quintessentially Stallone

Premiering at the Cannes Film Festival before hitting theaters, Cliffhanger did not earn a lot of praise from critics. But it was one of the highest grossing movies of the year, making $255 million at the box office worldwide. Directed by Renny Harlin, it featured breathtaking terrain views and did not hold back on the action. Stallone was in top physical form as the haunted Walker. With the gripping plot and stunning cinematography, his tortured but tenacious main character was a force to be reckoned with.

3 Antz (1998)

The list could have very easily excluded one of the best Sylvester Stallone movies of the 1990s, if we had taken into account live-action only. But in the animated world, the action superstar voiced Weaver, a strong and kind soldier ant in DreamWorks Animation’s debut film, Antz. The movie follows Z, a neurotic worker ant who dreams of a life beyond the colony. Z falls in love with Princess Bala, and when the colony faces a huge threat, he rises to the occasion and saves the day.

Stallone Infuses Heart Into the DreamWorks Classic

Antz is an underdog story like no other. Woody Allen voices the main character, the courageous ant who becomes a hero and leads a revolution. Sharon Stone lends her charm to his love interest. As for Stallone, his vocal performance as Weaver brings warmth and humor to the film and complements Z perfectly. Antz was hailed by critics as an insightful, witty, and engaging family comedy that relies on universal themes of self-discovery and redemption.

2 Demolition Man (1993)

Directed by Marco Brambilla in his directorial debut, Demolition Man transports you to San Angeles – an ultra-sanitized, futuristic merger of Los Angeles, San Diego, and Santa Barbara – and tells the story of John Spartan. A sergeant for the Los Angeles Police Department, he was cryogenically frozen in 1996 along with his nemesis, a psychopathic criminal named Simon Phoenix, and thawed out in 2032. Now in a world where violence isn’t normal, John must confront and recapture Phoenix any way he can.

Classic Sci-Fi With Satirical Edge

What begins as a standard sci-fi manhunt soon escalates into an all-out explosive action showdown between Spartan and Phoenix, played by Stallone and Wesley Snipes respectively. The former brings an intensity to his role of an out-of-time cop learning the new society’s peace-keeping norms. Snipes, on the other hand, is magnetic as the antagonist. The movie also has a unique brand of humor and highly imaginative visuals, which makes the viewing experience absolutely enthralling.

1 Cop Land (1997)

Cop Land is James Mangold’s sophomore directorial effort, followed by 1995’s Heavy. It is a compelling crime drama where Stallone plays Freddy Heflin, a quiet sheriff in a small New Jersey town populated primarily by New York City cops. His admiration for the officers runs deep, and Heflin himself wishes to join their ranks one day. But when he discovers that the cops are corrupt and are connected with the mob, engaging in practices like smuggling, he finds himself taking a stand and risking his own life in the process.

One of Stallone’s Most Authentic Performances

As the decade neared toward its end, Sylvester Stallone had established himself as a nuanced actor willing to venture into unknown territories. With Cop Land, he was able to deliver a more subdued, thoughtful, and layered performance compared to his other action-packed movies. He was accompanied by a stellar cast of heavy-hitters like Robert De Niro, Harvey Keitel, and Ray Liotta. The movie marked a dramatic departure for Stallone and earned him incredible praise. While not a blockbuster, Cop Land has its own little cult following.