The 10 Most Underrated Movie Villains of The 1990s

5. Jennifer Jason Leigh as Hedra Carlson in Single White Female

Single White Female

While Single White Female may fall into the typical formula of the psycho female thriller that the 1990s loved to make, but the same cannot be said for the film’s main antagonist. The plot revolves around Allison Jones (Bridget Fonda) searching for a roommate after a breakup from her fiancé Sam Rawson (Steven Weber). Allison eventually chooses a woman named Hedra Carlson (Jennifer Jason Leigh) to be her new roommate. Allison and Hedra quickly bond, but as Allison starts to reconsider her engagement, Hedra grows jealous and unstable. As Allison discovers new details about her roommate’s past life, Hedra’s efforts to have Allison all to herself become deadly.

Simply stated, Leigh is spectacular in this role. Leigh does a tremendous job of portraying the multifaceted sides of Hedra’s personality. Viewers see Hedra as a vulnerable, needy, delicate person and a total psychopath. Her third-act massive freak out must also be praised for its intensity. This grandiose breakdown towards the end of the movie is staged wonderfully and allows Leigh the time to work up to chilling emotions that range from unnervingly pathetic to dangerously demanding. Her expressions alone strike worry and anxiety into the hearts of audiences as they watch Hedra unravel.

The word groundbreaking may never be associated with Single White Female, but Leigh’s villainous performance is amazing none the less.


4. John Malkovich as Cyrus the Virus in Con Air

Con Air

In all of its corny, action-packed goodness, Con Air gives audiences a villain too enjoyably over-the-top to forget. In the movie, a newly paroled army ranger Cameron Poe (Nicolas Cage) is returning to his wife (Monica Potter) but must fly home aboard a prison transport with a group of seriously dangerous criminals. Along with his cronies, Diamond Dog (Ving Rhames) and Baby-O (Mykelti Williamson), serial killer Cyrus “The Virus” Grissom (John Malkovich) hijacks the plane to set up an escape plot in mid-flight. During this crisis, Poe tries to stop Cyrus by secretly working with U.S. Marshall Vince Larkin (John Cusack).

Even with the ensemble cast that includes Hollywood heavy hitters like Cage and Buscemi (just to name a few), Malkovich manages to steal every scene he is in. Malkovich is clearly having fun with this role, and if he is not, he is doing an amazing job of faking it. The character of Cyrus is intelligent and outlandish in the best possible way. Cyrus’s intellect gives him the ability to command the other criminals and therefore, make him a credible villain. However, Cyrus is also zany enough to truly sell the entertainment value of Con Air and garner audience investment.

With a name like Cyrus the Virus, viewers know they are in for a good time.


3. Edward Norton as Aaron in Primal Fear (*Spoiler Alert Ahead*)

Primal Fear is a solid crime procedural, but the movie is taken to new heights of success because of the three-dimensional characters, which includes the well-crafted villain of this film. The movie follows defense attorney Martin Vail (Richard Gere). He is a lawyer who takes on jobs for prestige and money rather than the good of humanity. When Vail’s latest case involves an altar boy named Aaron (Edward Norton) accused of murdering the archbishop of Chicago, he finds that what seemed to be a simple case takes a darker and more dangerous turn.

Aaron is master villain in every sense of the word. This villain reveal does not just creep audiences out, it shakes viewers to their core. Throughout the movie, spectators feel sorry for Aaron. The more movie-goers spend time with Aaron the more they feel sympathy for the character. Therefore, it is a complete surprise when Aaron turns out to be the villain. He is so convincing as an innocent victim suffering from serious mental illness that viewers almost do not believe it. By the end of the film, the way Aaron manipulates everyone on screen is heartbreakingly astounding.

Thanks to brilliant writing and Norton’s acting abilities, Aaron is an impressively shocking baddy.


2. Sarah Michelle Gellar as Kathryn Merteuil in Cruel Intentions

Cruel Intentions (1999) - Kathryn Merteuil

Diving into the dark underbelly of the teenage rich, Cruel Intentions presents an intriguing villain in Kathryn Merteuil. In the movie, chaste Annette (Reese Witherspoon) becomes a pawn in Sebastian (Ryan Phillippe) and Kathryn’s (Sarah Michelle Gellar) bet of sexual conquest when she promotes abstinence until marriage in an article in Seventeen Magazine. Unfortunately for Sebastian, he starts to develop genuine feelings for Annette and begins to question if he can go through with his and Kathryn’s malicious plan.

Kathryn Merteuil is not the typical antagonist found in a film directed towards teens nor is she a standard bully that audiences have seen in countless high-school focused movies. Kathryn seeks more than vapid popularity. She wants control and dominance while living in a society that constantly burdens her with a need for perfection. Since she cannot beat the system, Kathryn makes people suffer or she makes everyone her pawns in a fascinating power play that develops and evolves throughout the film. As a result of her cunningness and determination, Kathryn seemingly finds a way to win even when she is losing.

With sophistication, sex appeal, wit, and a fantastic wardrobe, Kathryn is a captivating villain to watch.


1. Viggo Mortensen as the Devil in The Prophecy

The Prophecy

As one of the greats to play the Devil incarnate, Viggo Mortensen shines as an outstanding villain. In the Prophecy, the wicked angel Gabriel (Christopher Walken) has come to earth to strengthen his powers by claiming the evil soul of a psychotic veteran. The good angel, Simon (Eric Stoltz), wants to stop Gabriel’s plan, and attempts to do this by hiding the man’s spirit in a little girl (Moriah Shining Dove Snyder). With a cosmic battle beginning, a liturgically knowledgeable cop (Elias Koteas) tries to protect the child and get help from an unlikely and hellish source (Viggo Mortensen).

When done by so many others, it is hard to believe anything new and original can be brought to a depiction of the devil. Legendary actors such as De Niro and Pacino (who we will see on this list shortly) have all given amazing performances as Lucifer. However, none of them match the eerie tranquility and chilling energy of Mortensen’s portrayal. His calmness is never mistaken for weakness. Rather, Mortensen as Satan keeps audiences on the edge of their seats as they only see tiny glimpses of the more animalistic beast underneath his sly and unshaking confidence.

Along with his attitude, this devil’s non-bias nature also makes him a terrifying villain. While Mortensen’s Lucifer does fight against Gabriel, his motives are anything but good. Mortensen as Mephistopheles has a pure disregard for the world, humanity, and God. Everything he does to help the child is not out of love or personal vendettas and this is a key element that makes Mortensen’s performance so fresh and memorable.

Mortensen’s Lucifer is more than just a great devil of the 1990s, it is an icon representation of Beelzebub that is timeless.