The 1990s proved a turbulent time for Sylvester Stallone’s career after the highly successful decade that was the 1980s. As the cinematic landscape shifted and action films developed, he found himself picking roles either too similar to previous outings or too dissimilar. Whether it be his often maligned comedies or his attempts to recapture the success of Stallone’s best films like First Blood or the previous Rocky movies.
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There are still plenty of gems to be found in his work throughout the decade, with some of his best acting on display. He has always had an inconsistent track record with the projects he has picked every decade. Varying from highs like Creed to low points like Rhinestone, but no matter what, Stallone has remained a towering figure in blockbuster cinema. Good or bad, there is rarely a boring Stallone project and many of these movies prove that.
12 The Good Life (1997)
Directed By Alan Mehrez
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The Good Life ComedyCrime
Three guys move from New Jersey to Miami, where two of them end up killing the third.
Release Date 1997-00-00 Cast Dennis Hopper , Beverly D’Angelo , Sylvester Stallone , David Carradine Runtime 95 Minutes Main Genre Comedy
A curious entry into Stallone’s body of work, it is highly likely that one has never seen, let alone heard of The Good Life. The movie was a passion project by his brother, Frank Stallone, and followed three golf buddies moving to New Jersey, with one being killed by the others. The movie features an assortment of character actors and celebrities, such as Dennis Hopper, Andrew Dice Clay, David Carradine, and Tony Sirico.
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Stallone agreed to make a cameo in the film as a favor to his brother, but later his scene was used heavily in the marketing, which prompted a lawsuit. He sued them for his usual salary of $20 million, and the case was settled out of court later. The film was subsequently shelved and has never seen the light of day, but according to all reports, it was a dud not meant for release.
11 Stop! Or My Mom Will Shoot (1992)
Directed By Roger Spottiswoode
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Stop! Or My Mom Will Shoot PG-13ActionComedy
Stop! Or My Mom Will Shoot is a 1992 action-comedy film starring Sylvester Stallone as a tough police sergeant whose overbearing mother, played by Estelle Getty, becomes an unexpected partner in his police work. Directed by Roger Spottiswoode, the film blends elements of crime investigation with familial comedy as Stallone’s character navigates his complex relationship with his meddlesome mother.
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*Availability in US Release Date February 21, 1992 Writers Blake Snyder , William Osborne , William Davies Cast Sylvester Stallone , Estelle Getty , JoBeth Williams , Roger Rees , Martin Ferrero , Gailard Sartain Runtime 87 minutes Director Roger Spottiswoode Main Genre Action Expand
Stop! Or My Mom Will Shoot has become somewhat legendary for being such a misfire, from conception to eventual release. The film follows a cop played by Stallone that is visited by his overbearing mother, played by the usually terrific Estelle Getty. It was an odd choice to combine the two stars, Stallone’s performance style hardly matching Getty’s experience from The Golden Girls. It is a wildly unfunny movie and fails to capture any of what makes these two stars charismatic.
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According to Arnold Schwarznegger, he tricked Sylvester Stallone into taking the role by leaking that he was interested in what he considered a horrible script.
The film was clearly an attempt by Stallone to recapture the success that Arnold Schwarzenegger managed with Kindergarten Cop.Stallone has never had much success in the comedy genre, and this movie is a clear example of why. It is a weak script, an even weaker concept, and its failure at the box office proved that.
10 The Specialist (1994)
Directed By Luis Llosa
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Despite being a box office hit in 1994, The Specialist has faded from people’s memories over the years. It sees Stallone playing a hitman hired by Sharon Stone’s femme fatale in order to exact vengeance against the man that killed her parents. It is absolutely ridiculous and suffers from a great many flaws in both its story and execution. It features a litany of strange choices, from a crazed James Woods performance to its completely languid pacing.
Related Every Time Sylvester Stallone Was Tricked Into Making A Movie
Sylvester Stallone has starred in some truly terrible movies throughout his career, and in some cases, he was tricked into taking part in them.
It is this clear lack of care that makes The Specialist such a bore to watch, though it does feature a good few choices that are ridiculous enough to enjoy. This includes one of Sharon Stone’s better performances, which is played in such an over-sexualized manner that you have no choice but to have fun with it. It is a movie filled to the brim with underwhelming action, poor performances and an exceptionally overwrought plot.
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9 Rocky V (1990)
Directed By John G. Avildsen
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Rocky V PG-13DramaSport
Facing financial ruin and health issues, Rocky returns to his roots to train a promising young fighter. As he struggles to rebuild his life, tensions rise with his protege, culminating in a dramatic street fight that forces him to confront his past and reclaim his legacy.
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*Availability in US Release Date November 16, 1990 Writers Sylvester Stallone Cast Sylvester Stallone , Talia Shire , Burt Young , Sage Stallone , Burgess Meredith , Tommy Morrison , Tony Burton Runtime 104 Minutes Director John G. Avildsen Main Genre Drama Expand
If there is a low point in the Rocky franchise, this is certainly it. Featuring none of the absurdity that made Rocky IV fun and none of the drama that made the first an immediate classic, Rocky V ends up as an easy punching bag for the series. The film sees the titular protagonist losing the wealth that he built over the past four films and having to train a young fighter by the name of Tommy Gunn. It makes a fatal miscalculation by failing to properly develop the younger boxer.
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A fatal flaw of the film also comes from the simple lack of good boxing matches that take place throughout the film. While there is some enjoyment to be had in the street fight that causes Rocky to fight again, it feels too little, too late. The movie certainly has some moments, with Stallone’s scenes with real-life son Sage Stallone proving a highlight. Despite John G. Avildsen returning to direct after having done the first, it feels as though Karate Kid sequels rubbed off on him.
8 Judge Dredd (1995)
Directed By Danny Cannon
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Judge Dredd RCrimeAction Sci-Fi
Judge Dredd is a 1995 sci-fi action film based on the comic character of the same name. Set in a distant dystopian future, humanity has elected “Judges,” to deal out justice, who act as “judge, jury, and executioner” as they tend to the lawless world of Mega-City One. But when Judge Dredd is framed for murder by his own brother, Dredd will strike back against him to reestablish the rule of Law and bring him to justice.
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*Availability in US Release Date June 30, 1995 Writers Steven E. de Souza , William Wisher Jr. Cast Armand Assante , Joan Chen , Rob Schneider , Sylvester Stallone , Max Von Sydow , Jurgen Prochnow , Diane Lane Runtime 96 minutes Director Danny Cannon Studio(s) Disney Distributor(s) Disney Expand
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Upon release and to this day, Danny Cannon’s Judge Dredd was a colossal failure for any fans of the comic books. Infamously removing the titular hero’s helmet early in the film’s runtime, the movie was maligned by fans and critics alike for its failure to elevate the source material. The movie saw Stallone’s hero framed for murder by his half-brother and having to thwart his attempts to take over the dystopian city.
A 2011 adaptation entitled
Dredd
has somewhat erased the memory of this film for being such an immediate classic.
Any positives that can be attributed to the film certainly come from the production design and costumes, which live up to the bold aestheticism of the comics. Gianni Versace produced the suit for Stallone, which has since become iconic for its eagle decal and codpiece. It is an interesting beast of a movie and struggles to live up to the iconic source material on which it is based.
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7 Daylight (1996)
Directed By Rob Cohen
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10/10 Daylight PG-13ActionAdventureDrama
Daylight is a disaster thriller film directed by Rob Cohen. Sylvester Stallone stars as Kit Latura, a former Emergency Medical Services chief, who must lead a group of survivors through a perilous journey after a catastrophic explosion traps them inside the Holland Tunnel. Joining him are Amy Brenneman as writer Maddy Thompson and Viggo Mortensen as adventurous celebrity Roy Nord.
Release Date December 6, 1996 Writers Leslie Bohem Cast Sylvester Stallone , Amy Brenneman , Viggo Mortensen , Dan Hedaya , Jay O. Sanders , Karen Young , Claire Bloom , Vanessa Bell Calloway Runtime 114 Minutes Director Rob Cohen Main Genre Action Expand
The only disaster movie that Sylvester Stallone had appeared in, Daylight, was a shift in input from his other work in decades prior. It paired the star with an ensemble of actors as they become trapped in the collapsing Holland tunnel. While the film’s premise appears to offer a good deal of excitement, Rob Cohen never seems to manage an exciting pace. The explosion that triggers the tunnel collapse is perhaps the highlight and features some suitably destructive crashes.
Stallone’s son Sage also makes an appearance in this as a criminal who becomes trapped in the tunnel.
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The ensemble is also the strongest element of the film, but mostly because Stallone’s lead is considerably less interesting than other characters. He plays an ex-chief of medical emergency services now working as a taxi driver, which is a little too ridiculous to believe. Performances by Stan Shaw, Amy Brenneman, and especially Viggo Mortensen shine, but it is all in favor of a weak script.
6 Oscar (1991)
Directed By John Landis
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10/10 Oscar PGComedy
Oscar is a 1991 comedy film directed by John Landis, starring Sylvester Stallone as Angelo “Snaps” Provolone, a gangster who promises his dying father to go straight. The plot follows Snaps’ efforts to become an honest businessman while dealing with a series of comedic misunderstandings and complications. The film also features performances by Marisa Tomei, Ornella Muti, and Peter Riegert.
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*Availability in US Release Date April 26, 1991 Writers Jim Mulholland , Michael Barrie , Claude Magnier Cast Sylvester Stallone , Marisa Tomei , Vincent Spano , Ornella Muti , Tim Curry , Peter Riegert , Chazz Palminteri , Martin Ferrero , Harry Shearer , Kirk Douglas , Paul Greco , Richard Foronjy , Joey Travolta , Yvonne De Carlo , Don Ameche , Richard Romanus , arleen sorkin , William Atherton , Ken Howard , Eddie Bracken , Tony Munafo , Kurtwood Smith , Art LaFleur , Linda Gray , Robert Lesser , Joycelyn O’Brien , Mark Metcalf , Sam Chew Jr. , Elizabeth Barondes , Sal Vecchio , Danny Goldstine , Kai Wulff , Marshall Bell , Tom Grant , Louis D’Alto , Rick Avery , Jim Mulholland Runtime 109 Minutes Director John Landis Main Genre Comedy Expand
A re-make of a French film by the same name, Oscar saw Stallone working in a comedy of errors. Inspired by screw-ball comedies of the 1930s, the film follows a gangster as he attempts to live true to his father’s dying wish that he go straight. Stallone works with a highly talented cast, including Tim Curry, Marisa Tomei, and Chazz Palminteri. While the cast all do a great job, it at times feels as though Stallone is drowned out by far better comedians and never able to shine despite being the lead.
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It is one of John Landis’ best movies, and his direction along with the supporting cast help elevate the film from being another of Stallone’s failed comedy projects. Marisa Tomei is especially strong, even landing her role in My Cousin Vinny because the director saw her on set. It was lambasted upon release, despite a two thumbs-up review from Siskel and Ebert. By no means a perfect film and far from the best in Landis’ career, Oscar proves the strength of a good supporting cast.
5 Antz (1998)
Directed By Eric Darnell & Tim Johnson
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Antz PGAdventureComedy
Antz is an animated film set in a colony where a neurotic worker ant named Z falls for a princess. His journey takes an unexpected turn when he swaps roles with a soldier ant, leading him to face a menacing general and an impending battle against termites.
Release Date October 2, 1998 Writers Todd Alcott , Chris Weitz , Paul Weitz Cast Woody Allen , Sharon Stone , Jennifer Lopez , Sylvester Stallone , Christopher Walken , Dan Aykroyd , Anne Bancroft , Danny Glover , Gene Hackman Runtime 83 minutes Director Eric Darnell , Tim Johnson Studio(s) DreamWorks Animation , Pacific Data Images Distributor(s) DreamWorks Pictures Main Genre Adventure Expand
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Since its release in 1998, Antz has developed somewhat of an odd reputation. Being released only two months before the extremely similar A Bug’s Life, the film was actually received very well upon release by critics and audiences alike. It follows the story of a disillusioned worker ant that falls in love with the princess of his colony, only to become wrapped up in a power struggle. Including Sylvester Stallone, the film has an absurdly talented voice cast with Gene Hackman, Jennifer Lopez, Sharon Stone and even more lending their talents.
Despite remaining a childhood classic for a lot of people, a general critical re-evaluation has made Antz a little less esteemed. The movie, for all its charm, is tonally confused and features some truly horrific moments. An ant massacre at the hands of termites is the most notable and has come to scar a good few children throughout the years. Stallone’s supporting turn is a lot of fun, but the overall movie feels misdirected.
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4 Assassins (1995)
Directed By Richard Donner
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Assassins (1995) RActionCrimeThriller
Assassins (1995) is a thriller directed by Richard Donner, starring Sylvester Stallone and Antonio Banderas. Stallone plays Robert Rath, a professional hitman aiming to retire while Banderas portrays Miguel Bain, a younger assassin challenging Rath’s status. As they face off in a deadly game, Rath protects a target, played by Julianne Moore, from both Bain and his own dark past in a high-stakes battle of wits and survival.
Release Date October 6, 1995 Writers Lilly Wachowski , Lana Wachowski , Brian Helgeland Cast Sylvester Stallone , Antonio Banderas , Julianne Moore , Anatoli Davydov , Muse Watson , Steve Kahan , Kelly Rowan , Reed Diamond , Kai Wulff , Kerry Skalsky Runtime 133 Minutes Director Richard Donner Main Genre Action Expand
Assassins is by no means the high point of Richard Donner’s directing career, but it is certainly a fun and explosive watch from start to finish. The film features Sylvester Stallone and Antonio Banderas as warring assassins in a cat and mouse chase, each one attempting to one up the other at every turn. The film features a great supporting turn from Julianne Moore and sees her on the run from Banderas’ sadistic killer.
The original script was penned by the Wachowskis, but was rewritten by Brian Helgeland. They attempted to have their names removed, but were unsuccessful.
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While the film is ostensibly a Sylvester Stallone project, it is Antonio Banderas’ performance that makes the film such an exciting watch. The action sequences are extremely bombastic, with explosions and machine guns galore. A shoot out during a funeral and a taxi cab confrontation between the two leads make for memorable moments in an otherwise lackluster plot. It is definitely not as good as the cast deserves, but it is certainly a fun watch.
3 Cliffhanger (1993)
Directed By Renny Harlin
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Cliffhanger RActionAdventureThriller
Cliffhanger is an action thriller directed by Renny Harlin, starring Sylvester Stallone as Gabe Walker, a mountain climber haunted by a tragic accident. Recruited by a group of criminals led by Eric Qualen (John Lithgow), Gabe is forced to recover their lost loot scattered across treacherous peaks. The film showcases stunning mountain vistas and intense action sequences, providing a high-stakes backdrop for Gabe’s quest for redemption and survival.
Release Date May 28, 1993 Writers Michael France , Sylvester Stallone Cast Sylvester Stallone , John Lithgow , Michael Rooker , Janine Turner , Rex Linn Runtime 112 Minutes Director Renny Harlin Studio(s) Carolco Pictures , Pioneer , Le Studio Canal+ , RCS Video Main Genre Action Expand
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Probably the closest Stallone got to recreating the 1980s films that made him a star, Cliffhanger sees him facing off against thieves in the Colorado Rockies. The movie features some really great action sequences and some of the best stunts to have ever been put on screen. Most notably, a plane stunt involving a criminal zip-lining from one plane to another in a truly death-defying feat. The movie also takes great advantage of its setting, snow-capped mountains and rock faces, perfectly back-dropping the violence.
The film is also elevated by John Lithgow’s scene chewing turn as British criminal mastermind, Eric Qualen. This matched with Michael Rooker’s supporting performance and Janine Turner’s portrayal of Stallone’s helicopter pilot girlfriend. It is a blast to watch and features some of the best action the movie star has taken part in, leading to one of the best films of his career. The film has had such a lasting legacy that a sequel is set to begin filming this year.
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2 Demolition Man (1993)
Directed By Marco Brambilla
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Demolition Man RActionCrimeSci-FiThriller
In the 1993 action movie Demolition Man, Sylvester Stallone stars as time-displaced police officer John Spartan, who struggles to adapt to the year 2032 after being cryogenically frozen for messing up a job. However, his old-school skills come in handy for innocent cop Lenina Huxley (Sandra Bullock) and the futuristic city of San Angeles when the criminal Simon Phoenix (Wesley Snipes) is thawed and the complacent authorities don’t know how to react.
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*Availability in US Release Date October 8, 1993 Writers Peter M. Lenkov , Robert Reneau , Daniel Waters Cast Sylvester Stallone , Wesley Snipes , Sandra Bullock , Nigel Hawthorne , Benjamin Bratt , Bob Gunton Runtime 115 minutes Director Marco Brambilla Studio(s) Warner Bros. Pictures Distributor(s) Warner Bros. Pictures Expand
As far as heroes and villains are concerned, Demolition Man definitely shows off some of the best of them. With a delightfully gruff performance from Stallone and an electric turn from Wesley Snipes, the movie feels unstoppable when they are on-screen. The film sees Stallone as a famed police officer who is cryogenically frozen for his explosive tactics, only to be thawed out in the year 2032 after his nemesis is released.
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The film features one of the better developed futuristic landscapes, with numerous laugh-out loud developments leading from the various inventions. Whether it be the three seashells that have replaced toilet paper or the reported restaurant wars, that left Taco Bell the only chain remaining. It is an excellent time and features a cavalcade of great actors such as Sandra Bullock, Benjamin Bratt, and Bill Cobbs. It is an absurdly fun time and one that will always have a place for fans of ’90s action bombast.
1 Cop Land (1997)
Directed By James Mangold
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10/10 Cop Land (1997) RCrimeDramaThriller Release Date August 6, 1997 Writers James Mangold Cast Sylvester Stallone , Harvey Keitel , Ray Liotta , Robert De Niro , Peter Berg , Janeane Garofalo , Robert Patrick , Michael Rapaport Runtime 104 minutes Director James Mangold Studio(s) Woods Entertainment , Across the River Productions Distributor(s) Miramax Films Main Genre Crime Expand
Before James Mangold would make a name for himself with films like Girl, Interrupted and Walk The Line, he directed the criminally underrated police drama Cop Land. It is a movie, unlike most of Sylvester Stallone’s other works, with him taking on a more complex character than his traditionally Stoic action heroes. The film follows the sheriff of a small New Jersey town mostly populated with New York police officers as he slowly uncovers the web of corruption beneath the idyllic surface.
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The movie saw Stallone gain 40 pounds and playing a character more reserved and unwilling to take a stand for much of the film. It plays out similarly to High Noon with the town slowly turning their backs on a sheriff, hoping to actually achieve something for once. Featuring one of the best casts assembled in the 1990s, with Harvey Keitel, Robert De Niro, Ray Liotta, and Janeane Garofalo all making appearances. It is a crime drama deserving of respect and especially appreciation for one of Sylvester Stallone’s best performances.
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