The 1990s were a terrific decade for movies. The action genre, in particular, saw the release of some of its most iconic outings, from Con Air to The Matrix. Taking advantage of technological advancement in the field of visual effects and contemporary audiences' thirst for action-packed adventures, these movies scored with critics and audiences. This decade saw no shortage of spectacles that have gone down in history as masterclasses in action filmmaking.

More often than not, a good action movie needs a good villain. The best action films of the '90s certainly had plenty of terrifically written, menacingly performed, memorable and iconic antagonists to offer. These iconic characters prove that, as long as there's a compelling villain, an action film can overcome almost any flaws it may have. From deranged and bloodthirsty killers to cold and calculating tacticians, these are the best villains in '90s action movies.

10 Simon Gruber (Jeremy Irons)

'Die Hard with a Vengeance' (1995)

Jeremy Irons as Simon Peter Gruber wearing sunglasses in ‘Die Hard With A Vengeance’ (1995)
Image via 20th Century Studios

The original Die Hard is not only Bruce Willis's best action movie but one of the best action films of all time. Its villain, Hans Gruber (portrayed by a never-better Alan Rickman), is one of the genre's most popular. His brother, on the other hand, is one of its most criminally underrated. Simon Gruber (a chilling Jeremy Irons) is the villain of the third film in the franchise, Die Hard with a Vengeance, where John McClane is paired with a Harlem store owner to save the Federal Reserve Building from Gruber's evil schemes.

While Hans proved to be a master manipulator and a brilliant strategist, Simon has the intelligence and impenetrability of his brother multiplied by a hundred. Genuinely mysterious and scary, two characteristics not often found in action movie villains, Simon is a hell of a force to be reckoned with and gives McClane a truly hard time. Irons flawlessly portrays him with elegance and zeal, making him as intimidating as he is fascinating.

Die Hard: With a Vengeance
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Action
Crime
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Release Date
May 19, 1995
Director
John McTiernan
Cast
Bruce Willis , Jeremy Irons , Samuel L. Jackson , Graham Greene , Colleen Camp , Larry Bryggman
Runtime
131 mins
Writers
Jonathan Hensleigh , Roderick Thorp

9 Cyrus "The Virus" Grissom (John Malkovich)

'Con Air' (1997)

John Malkovich as Cyrus 'The Virus' Grissom, pointing a gun at a bunny plushie in 'Con Air'
Image via Walt Disney Studios Motion Pictures

Nicolas Cage is one of those actors whose every movie is endlessly rewatchable, but Con Air is, without a doubt, one of his most enjoyable. Newly paroled ex-con and former U.S. Ranger Cameron Poe finds himself trapped in a prisoner transport plane, where the prisoners, led by Cyrus "The Virus" Grissom, seize control.

Cyrus "The Virus" has one of the qualities that are most important in a great villain: unpredictability. He's devilishly evil and devoid of any remorse or morality, which, mixed with his capacity to concoct masterful plans, makes him terrifying to viewers. Cyrus knows that this is his last shot at freedom, which ups the stakes and consequently makes his actions result in more suspenseful situations. It helps that John Malkovich is at his most over-the-top, delivering a suitably unhinged performance that makes the whole thing all the more entertaining.

con air
Con Air
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Action
Crime
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Release Date
June 5, 1997
Director
Simon West
Runtime
115
Writers
Scott Rosenberg

8 Norman Stansfield (Gary Oldman)

'Léon: The Professional' (1994)

Norman Stansfield walking through a curtain of beads in 'Leon_ The Professional' (1994)
Image via The Walt Disney Company France

Directed by groundbreaking French filmmaker Luc Besson, Léon: The Professional is one of the most acclaimed action movies of the '90s. The plot centers on a 12-year-old girl named Mathilda, who's reluctantly taken in by professional assassin Léon after drug lord Norman Stansfield kills her family. Thirsty for revenge, she becomes his protégée and starts to learn the secrets of the trade.

Stansfield is one of the most underrated movie villains of the '90s. Perfectly played by Oscar winner Gary Oldman in an explosive, delightfully and cleverly overacted performance, he's an unhinged villain with a passion for Beethoven and screaming. What makes him most intimidating is that he's not just any kind of drug lord; he's also a corrupt DEA agent. With the scales tipped in his favor, it becomes an even greater challenge for Léon and Mathilda to take him down.

Leon the Professional Film Poster
Leon: The Professional
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Action
Crime
Drama
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Release Date
November 18, 1994
Director
Luc Besson
Cast
Jean Reno , Gary Oldman , Natalie Portman , Danny Aiello
Runtime
110 minutes
Writers
Luc Besson

7 Bodhi (Patrick Swayze)

'Point Break' (1991)

Kathryn Bigelow's cult classic Point Break is a crime thriller where an F.B.I. agent goes undercover to catch a gang of surfers who are also bank robbers. Stylish and over-the-top, it was the adrenaline-fueled and action-packed film that made Keanu Reeves an action star. If there's someone who steals the spotlight, though, it's Patrick Swayze as Bodhi, the leader of the surfer-criminal group that Reeves's character is sent to catch.

Swayze makes the audience root for Bodhi throughout the movie's whole runtime. He's a charming guy who only wants to get enough money to chase more thrills, and he's also undeniably cool. As such, while anticipating the moment when he's finally caught and put behind bars, viewers are constantly yearning to get more scenes with Bodhi. He's a cool villain who effortlessly fits the film's "surfer bro" tone and a major reason behind its continued success.

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6 Agent Smith (Hugo Weaving)

'The Matrix' (1999)

Agent Smith looking intently in The Matrix
Image via Warner Bros.

To put it mildly, The Matrix revolutionized the action movie genre. Aside from its groundbreaking visual effects, it showed that action films could have philosophically profound plots without sacrificing any of the thrills and edge-of-your-seat action. It's the tale of Neo, a computer hacker led to a forbidden underworld where he discovers that the life he knows is the elaborate deception of an evil cyber-intelligence, personified as the pragmatic Agent Smith.

Portrayed by an impassable Hugo Weaving, Agent Smith's mission is to maintain order in the simulation and eliminate all threats to said order. Slick, smart, and authoritative, he fulfills his mission with the utmost efficiency, making ample use of some pretty sick martial arts skills. This unique mix of deathly precision makes him an incredibly fun presence in action scenes, which the Wachowski sisters film with tremendous fervor and uncontainable energy.

The Matrix Poster
The Matrix
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Release Date
March 30, 1999
Runtime
136 minutes
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5 Castor Troy (Nicolas Cage)

'Face/Off' (1997)

Castor Troy dressed as a priest and screaming maniacally in Face Off
Image via Touchstone Pictures

John Woo's Face/Off is one of the most creative, delightfully campy, and unbelievably over-the-top action extravaganzas of the '90s. It sees F.B.I. agent Sean Archer recur to face transplant surgery to assume the identity of criminal Castor Troy, who murdered his son, in order to foil a terrorist plot. However, Troy is able to assume Archer's identity and vows revenge.

First, Nicolas Cage plays Archer with an admirable amount of restraint, considering his unique acting style. It's only after Troy starts wearing Archer's face that the actor goes full-on Cage, delivering one of the most spirited and over-the-top performances ever captured on screen. Troy's murderous energy and unpredictable criminal mind make him absolutely terrifying. Bouncing off of John Travolta's Sean Archer flawlessly, the duo makes Face/Off an incredibly good time.

Face Off Poster
Face/Off
R
Science Fiction
Action
Thriller

Release Date
June 27, 1997
Director
John Woo
Cast
Nicolas Cage , John Travolta , Joan Allen , Gina Gershon , Alessandro Nivola
Runtime
139 minutes

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4 T-1000 (Robert Patrick)

'Terminator 2: Judgment Day' (1991)

The T-1000 dressed as a cop aiming a gun at someone off-camera in Terminator 2 - 1991
Image via Tri-Star Pictures

Thanks to its stunning visuals, engaging story and characters, and action scenes that have aged like fine wine, Terminator 2: Judgment Day is one of the best action films ever made. It finds a cyborg, identical to the one that failed to kill Sarah Connor years prior, traveling to the past to protect her son from an even more advanced Terminator who's been sent back in time to eliminate him.

This highly advanced cyborg is the T-1000, a seemingly indestructible android capable of using its liquid metal skin to shapeshift and move through tight spaces. Robert Patrick offers an incredibly scary and stoic performance as the T-1000, which is essential in making him feel as unstoppable as he does. Action movies are always best when the stakes are high, and with a villain as powerful as this one, T2 keeps the stakes astronomical all the way until the end.

Terminator 2 Judgment Day Film Poster
Terminator 2: Judgment Day
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Action
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Release Date
July 3, 1991
Director
James Cameron
Runtime
137 minutes
Writers
James Cameron , William Wisher Jr.

3 Lady Eboshi (Minnie Driver)

'Princess Mononoke' (1997)

Lady Eboshi with one of her rifles turning around and smiling confidently in Princess Mononoke.
Image via Toho

Often praised as one of Studio Ghibli's best films, Princess Mononoke is about a cursed warrior on a journey to find a cure. In his quest, he finds himself in the middle of a war between a mining colony and the gods of the forest. Surprisingly violent and action-packed for a Hayao Miyazaki movie, Princess Mononoke is also one of his most thematically deep and complete works.

Some of its themes are best embodied by the story's antagonist, Lady Eboshi, the leader of Irontown and rescuer of its people. A masterclass in writing morally ambiguous villains who have a good point, Princess Mononoke explores the intricacies of conflict, with Lady Eboshi standing out as perhaps the best antagonist in Ghibli's whole filmography. Far from a simple villainous caricature, Lady Eboshi feels like a truly complicated human being. Her motivations are easy to empathize with but remain extreme and often reprehensible, making the action sequences all the more gripping.