The ’90s were a great decade for movies in general, with action movies being at the center of all things. With films likeThe Matrix, Terminator 2: Judgment Day,andHeat,the ’90s were responsible for birthing iconic action heroes, along with iconic action villains.
While the heroes got most of the attention and took the cake, the villains of the ’90s were mostly overlooked and sidelined. Though, when looked at closely, it’s actually the villains that have single-handedly raised the stakes and taken the entertainment quotient up by a few levels. Whether crazy cold-blooded murderers, or sadistic psychopaths, the villains not only carved out a space in our memories, but continue to inspire modern-day films and filmmakers.

10Howard Payne (Dennis Hopper) - Speed (1994)
Speedsees Keanu Reeves star as an LAPD officer pitted against a disgruntled bomb expert inDennis Hopper. The film takes place on a bus that’s been rigged with a bomb that will go off if the speed of the bus drops below 50mph. Contradictory to Keanu Reeves’ portrayal of straight-edge LAPD officer Jack Traven, Dennis Hopper’s Howard Payne is cold and sadistic in nature, unwilling to stop until all his demands have been met.
9Cyrus ‘The Virus’ Grissom (John Malkovich) - Con Air (1997)
Operating on a similar narrative trope asSpeed,Con Airworks as a high-octane action movie that sees Nicolas Cagetrapped on a planewith a bunch of criminals, led by an extremely cunning and crooked Cyrus Grissom (John Malkovich). Cyrus isn’t an average criminal with a bit of guts, he’s rather very cunning and creepy, with an uncanny knack for being at the right place at the right time.
Related:These Are the Best John Malkovich Movies, Ranked
8Ivan Korshunov (Gary Oldman) - Air Force One (1997)
Gary Oldman’s reputation for playing the bad guy was at its peak during the ’90s, with his performance as Ivan Korshunov being one of his crown jewels. Oldman’s Korshunov is nothing short of crazy, as he’s willing to butcher anybody who stands between him and his ideals. Unlike conventional action movie villains, Korshunov is aware of his actions yet seems to be fueled by his twisted inner moral compass.
Related:Gary Oldman’s Best Action Movies, Ranked
7Penguin (Danny DeVito) - Batman Returns (1992)
Many consider Tim Burton’sBatman Returnsto be one of the most crazy films in the superhero series, withDanny DeVitodoing a stellar job at upping the bizarre quotient. While it’s no secret that the Joker is Batman’s arch nemesis,DeVito’s Penguin comes dangerously closewith his idiosyncratic oddities and absurd plans for the world.
Related:Danny DeVito’s Best Performances, Ranked
6Norman Stansfield (Gary Oldman) - Léon: The Professional (1994)
Norman Stansfield fromLéon: The Professionalis anotherGary Oldmanmasterpiece on the list. Unlike the ruthlessly motivated Korshunov, Stansfield is an all-out sadist with no shard of humanity in him. Yet Stansfield is not very over the top with his antics, he’s rather internally suppressive, maskinga monster under the garb of an officer.
5Castor Troy (Nicolas Cage and John Travolta) - Face/Off (1997)
Face/OffpresentsNicolas Cagein his most purely crazy form, going full throttle in the most over-the-top fashion. The film’s title also works as a pun that defines the premise aptly and has Nicolas Cage andJohn Travoltaface off against each other. The film’s plot is full of twists and turns as FBI agent Sean Archer (John Travolta), undergoes plastic surgery to impersonate his son’s killer, Castor Troy (Nicolas Cage).
Things take a turn for the bizarre when Castor Troy impersonates Archer, sending the narrative into a crazy head-spin.

4Neil McCauley (Robert De Niro) - Heat (1995)
Michael Mann’sHeatcreated a world of buzz when it released, promising a face-off for the ages between Al Pacino’s straight-edge cop, Vincent Hanna, versusRobert De Niro’s slick criminal, Neil McCauley. Despite being on separate sides of the law, both Hanna and McCauley are men of principles, sharing many similarities and traits. Due to their complexities in nature and profession,it’s hard not to fall in love with Mann’s characters, regardless of their outlook about the law.
3Darth Maul (Ray Park) - Star Wars: Episode I - The Phantom Menace (1999)
Darth Maul - Star Wars: Episode I: The Phantom Menace (1999) 20th Century Fox
Arguably one of the most terrifying villains intheStar Warsfranchise, Darth Maul’s unparalleled expertise in martial arts paired with his double-ended lightsaber solidified his status as one of the most menacing villains of the ’90s. Although it would have been interesting to see more of the devil-looking villain in the film, a large part of Darth Maul’s appeal lies in his sparing use, thereby creating a spark of terror whenever he enters the frame.

2Agent Smith (Hugo Weaving) - The Matrix (1999)
Hugo Weaving’s portrayal of thesinister A.I. program(Agent Smith), is the perfect marriage between capitalistic bureaucracy and computing precision. Weaving takes a paper character and removes from it any humanistic trait, which perfectly summarizes Agent Smith, a software’s interior hidden behind a man’s exterior.
1T-1000 (Robert Patrick) - Terminator 2: Judgment Day (1991)
Following in Arnold Schwarzenegger’s footsteps inThe Terminatorwas never an easy task. With Schwarzenegger’s larger-than-life persona and Herculean frame, it was smart on Cameron’s side to go for something opposite rather than outdoing what Arnold had brilliantly done. His answer to this conundrum lay inRobert Patrick’s mediocre build, offset with a more cunning and conniving operating system.
Paired with shape-shifting liquid technology and agile movements, the T-1000 came off as an even more terrifying cyborg than Schwarzenegger’s Terminator.

