The 1990s were a terrific decade for movies. The action genre, in particular, saw the release of some of its most iconic outings, fromCon AirtoThe 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.

Jeremy Irons as Simon Peter Gruber wearing sunglasses in ‘Die Hard With A Vengeance’ (1995)

10Simon Gruber (Jeremy Irons)

‘Die Hard with a Vengeance’ (1995)

The originalDie Hardis not onlyBruce Willis’s best action moviebut one of the best action films of all time. Its villain, Hans Gruber (portrayed by a never-betterAlan 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 chillingJeremy 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.

instar50194111.jpg

Die Hard: With a Vengeance

9Cyrus “The Virus” Grissom (John Malkovich)

‘Con Air’ (1997)

Nicolas Cageis one of thoseactors whose every movie is endlessly rewatchable, butCon Airis, 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 thatJohn Malkovichis at his most over-the-top, delivering a suitably unhinged performance that makes the whole thing all the more entertaining.

Samuel L. Jackson headshot

8Norman Stansfield (Gary Oldman)

‘Léon: The Professional’ (1994)

Directed by groundbreaking French filmmakerLuc Besson,Léon: The Professionalis 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 ofthe most underrated movie villains of the ’90s. Perfectly played by Oscar winnerGary Oldmanin 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.

instar53583397.jpg

Léon: The Professional

7Bodhi (Patrick Swayze)

‘Point Break’ (1991)

Kathryn Bigelow’s cult classicPoint Breakis 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 madeKeanu Reevesan action star. If there’s someone who steals the spotlight, though, it’sPatrick Swayzeas 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.

John Malkovich as Cyrus ‘The Virus’ Grissom, pointing a gun at a bunny plushie in ‘Con Air’

Watch on Tubi

6Agent Smith (Hugo Weaving)

‘The Matrix’ (1999)

To put it mildly,The Matrixrevolutionized the action movie genre. Aside fromits 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 impassableHugo 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 theWachowski sistersfilm with tremendous fervor and uncontainable energy.

The Matrix

5Castor Troy (Nicolas Cage)

‘Face/Off’ (1997)

John Woo’sFace/Offis 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 andover-the-top performances evercaptured on screen.Troy’s murderous energy and unpredictable criminal mind make him absolutely terrifying. Bouncing off ofJohn Travolta’s Sean Archer flawlessly, the duo makesFace/Offan incredibly good time.

Watch on Paramount+

4T-1000 (Robert Patrick)

‘Terminator 2: Judgment Day’ (1991)

Thanks to its stunning visuals, engaging story and characters, and action scenes that have aged like fine wine,Terminator 2: Judgment Dayis one ofthe 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,T2keeps the stakes astronomical all the way until the end.

Terminator 2: Judgment Day

3Lady Eboshi (Minnie Driver)

‘Princess Mononoke’ (1997)

Often praised as one of Studio Ghibli’s best films,Princess Mononokeis 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 aHayao Miyazakimovie,Princess Mononokeis 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 ambiguousvillains who have a good point,Princess Mononokeexplores the intricacies of conflict, withLady 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.

Princess Mononoke

2Neil McCauley (Robert De Niro)

‘Heat’ (1995)

The terms"slow-burn" and “action thriller"may not sound like they go together, but movies likeMichael Mann’sHeatprove the combination can result in one of the greatest films the genre has ever seen.Heatfollows a group of high-end professional thieves who get on the L.A.P.D.’s radar when they accidentally leave a clue at their latest heist.

Robert De Niromasterfully plays Neil McCauley, the leader of the gang of thieves.He’s a solitary former Marine who prides himself on his ability to avoid emotional connections, looking only to amass a good fortune to retire while avoiding prison. De Niro’s impeccable acting chops and Mann’s exceptional script make McCauley a fascinating villain and co-protagonist, and his dynamic withAl Pacino’s Lt. Vincent Hanna is all the more engrossing as a result.Heatoften ranks among the all-time best movies from the ’90s, rightfully so, and De Niro’s endlessly engaging McCauley is a huge reason for its success.

1Tyler Durden

‘Fight Club’ (1999)

Though he’s one of the most misunderstood antagonists from one of the most misunderstood films of the ’90s,Tyler Durdenis nevertheless one ofthe best movie villains of all time. He’s the most interesting character inFight Club, a spellbinding psychological thriller about an insomniac office worker and a reckless soap manufacturer who form an underground fight club.

Charmingly played byBrad Pittin one of the best works of his career,Tyler is a mystifying character who keeps evolving as the plot moves along. His unique connection to the protagonist is deeply compelling and magnificently executed, and his elusive, mercurial, shifting nature provides the movie with a strong anchor, allowingEdward Norton’s protagonist to experiment with the narrative. Tyler is charismatic yet menacing, morally ambiguous yet easy to love; all in all, the perfect ’90s action movie villain.

Fight Club

NEXT:The Best Movies With a Twist Villain, Ranked