From the big-budget thrills of T2 to the gritty realism of Heat, the 1990s gave way to some of the greatest action movies ever made. These action-packed classics came along with a handful of iconic villains.

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In GoldenEye, James Bond tangled with a former 00 agent who’d been presumed dead. In The Phantom Menace, Obi-Wan Kenobi bisected a devil-like Sith Lord with his fallen master’s lightsaber. In The Matrix, Keanu Reeves’ Neo simultaneously battled an army of computer programs in black suits and an existential crisis stemming from his destiny to become a messianic superhero.

Cyrus “The Virus” (Con Air)

Cyrus points pistol at a toy bunny in Con Air

Nicolas Cage starred in a bunch of high-octane, high-concept action movies throughout the 1990s. One of the most wildly entertaining is Con Air, in which Cage is trapped on a plane with a bunch of sadistic criminals.

John Malkovich leads the villains as Cyrus “the Virus.” Everybody in this movie is an exaggerated pulp archetype played to perfection by an overqualified actor like Steve Buscemi or Ving Rhames – or, indeed, John Malkovich.

Howard Payne (Speed)

Howard Payne holding a bomb in Speed

Described as “Die Hard on a bus,” Speed stars Keanu Reeves as a cop who finds himself on a bus that’s been rigged with a bomb that will explode if its speed drops below 50mph. The bomb was planted by psychotic bad guy Howard Payne.

Just as Reeves’ portrayal of Jack Traven as a straight arrow differentiates the character from the relatably flawed John McClane, Dennis Hopper’s portrayal of the villainous Payne as an unpredictable sadist differentiates him from the cold, collected Hans Gruber.

Darth Maul (Star Wars: Episode I – The Phantom Menace)

Darth Maul during the climactic duel in Star Wars The Phantom Menace

On the whole, The Phantom Menace was a very polarizing movie. Jar Jar Binks and the political discourse divided the Star Wars fan base. But one thing that all fans and critics could agree on was that the film’s villain was awesome.

An unparalleled martial artist who looks like the Devil, Darth Maul is one of the most terrifying Sith Lords in the Star Wars canon – and he’s responsible for the movie’s most devastating moment when he kills Qui-Gon Jinn in cold blood.

John Hammond (Jurassic Park)

John Hammond smiling in Jurassic Park

Richard Attenborough did a fantastic job of bringing John Hammond’s “dark Walt Disney” characterization to the screen in Steven Spielberg’s adaptation of Jurassic Park. The escaped dinosaurs terrorize the protagonists throughout the movie, but the real monster is the corporate overlord who played God and brought those dinosaurs back to life to increase his company’s profits.

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Dr. Ian Malcolm sums up Hammond’s delusions of grandeur perfectly: “Your scientists were so preoccupied with whether or not they could, they didn’t stop to think if they should.”

Neil McCauley (Heat)

Neil pointing a gun in Heat

Michael Mann’s slick L.A.-set neo-noir Heat is the quintessential cat-and-mouse thriller. It paired up Robert De Niro and Al Pacino on-screen for the first time ever. De Niro plays a bank robber named Neil McCauley, while Pacino plays the cop on his trail, Lieutenant Vincent Hanna.

Neil’s success as a bank robber stems from his ability to drop everything and move when the law is closing in, but he’s reluctant to leave Los Angeles after falling in love – which eventually becomes his downfall.

T-1000 (Terminator 2: Judgment Day)

T-1000 from Terminator 2 looking menacingly at the camera

James Cameron’s explosive, epic-scale sequel Terminator 2: Judgment Day shakes up the formula from the first movie. In the first one, Arnold Schwarzenegger’s T-800 was sent back in time to kill Sarah Connor to prevent the birth of her son, Resistance leader John Connor.

In T2, a reprogrammed T-800 is sent as a protector while the even more advanced T-1000, played chillingly by Robert Patrick, is the assassin assigned to kill John himself. The T-1000’s threat raises the stakes of the story’s conflict (and the spectacle of its action sequences).

Bodhi (Point Break)

Patrick Swayze as Bodhi in the back of a van in Point Break

Keanu Reeves and Patrick Swayze were perfectly matched in the lead roles of Johnny Utah and Bodhi in the buddy actioner Point Break. Utah is an undercover FBI agent who infiltrates a gang of surfers who also rob banks on the side.

Bodhi is the gang’s leader, who Utah finds so charismatic that he can’t bring himself to arrest him. Swayze is charming and mesmerizing enough to make this goofy premise believable.

Catwoman (Batman Returns)

Catwoman lying on a bed in Batman Returns

Danny DeVito was perfectly cast as the Penguin in Tim Burton’s Batman Returns, but Michelle Pfeiffer steals the show as the sequel’s other villain, Catwoman. Pfeiffer offers a quintessential take on the character as the ultimate femme fatale and shares terrific chemistry with Michael Keaton’s Caped Crusader.

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Pfeiffer’s Selina Kyle has a real sadistic edge. The actor plays her with a horror sensibility, similar to Jack Nicholson’s Joker in Burton’s previous Batman film.

Alec Trevelyan (GoldenEye)

Alec Trevelyan looks serious in Goldeneye

Pierce Brosnan’s James Bond was first introduced to audiences in GoldenEye. In the opening scene, 007 infiltrates a chemical weapons factory with fellow 00 agent Alec Trevelyan (006), played brilliantly by Sean Bean. Trevelyan is seemingly killed off in the opening mission, and the grief from his supposed death becomes the emotional backbone of Bond’s character arc throughout the movie.

Then, in the middle act, Bond is floored by the shocking twist reveal that not only is Trevelyan alive and well; he’s the latest villain tormenting MI6.

Agent Smith (The Matrix)

Hugo Weaving as Agent Smith smiling in The Matrix

Hugo Weaving gave a haunting performance as Neo’s arch-nemesis Agent Smith in The Matrix. He was one of the few saving graces in the critically panned sequels, too. The new Agent Smith in The Matrix Resurrections – played by Jonathan Groff – only served to highlight how perfect Weaving was for the role.

The Agents are sinister A.I.s tasked with taking out human simulacra that threaten the stability of the program. Weaving plays the role as a cold-hearted, gun-toting bureaucrat with a monotonous yet captivating voice.

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