What do most, if not all, of the best ‘90s movies have in common? Well, besides being the best representation of the final decade of the 20th century? They typically featured menacing, dastardly, sinister, and over-the-top villains that we sometimes remember more than the heroes who tried to stop them. But who are the meanest, the baddest, the most unforgiving villains of the 1990s? Funny you should ask…
Max Cady (Cape Fear)
Martin Scorsese’s 1991 remake of Cape Fear is a tense and terrifying psychological thriller with a frightening story about a convict seeking vengeance against his former defense attorney. There is just something so unsettling, so menacing, and straight-up mean about Robert De Niro’s portrayal of Max Cady that makes him an all-time villain. Maybe it’s the way he says “counselor” in that sinister tone.
Sheriff 'Little Bill' Daggett (Unforgiven)
Sheriff Daggett (Gene Hackman) is one mean son-of-a-gun in Clint Eastwood’s 1992 Best Picture winner, Unforgiven. He beats people, embarrasses them, and kicks them out of town, and that’s before his true callous nature is revealed later in the movie. Hackman, who could play a villain better than just about anyone else, manages to be incredibly evil while not being over-the-top.
Buddy Love (The Nutty Professor)
The 1996 remake of The Nutty Professor is one of the funniest Eddie Murphy movies as well as one where he plays more than one character. While his take on Sherman Klump is wholesome and tremendous, his portrayal of the kind-hearted professor’s evil alter ego, Buddy Love, is the stuff of legend. It’s as if an egotistical and crass AI watched Eddie Murphy: Delirious to come up with a mean, mean, mean character.
Eva Ernst (The Witches)
Even before Eva Ernst (Anjelica Huston) reveals herself to be The Grand High Witch in The Witches, the villain in this 1990 adaptation of a Roald Dahl classic is nothing but trouble. And unlike a lot of the characters on this list, Ernst wants to eat children, not just harm or toy with them. It doesn’t get much meaner than that.
Henry Evans (The Good Son)
If you were to put on The Good Son because you liked Macaulay Culkin’s work in the Home Alone movies, you’d probably be shocked to see his take on Henry Evans in The Good Son. Take every terrifying kid from horror movies and an extra level of mean, and you have this violent and psychotic ‘90s movie villain. The way he responds with “What if I did,” when asked if he killed his younger brother is wild. Just wild!
Shooter McGavin (Happy Gilmore)
Shooter McGavin (Christopher McDonald) is in the top tier of Adam Sandler movie villains as well as one of those ‘90s characters you just love to hate. There are no redeemable qualities, no chance of redemption, and no way anyone could like this guy. But still, the egotistical pro golfer who wants to make Sandler’s hockey-player-turned-golfer life as miserable as possible in Happy Gilmore is the stuff of legend.
John Doe (Seven)
Definitely one of the sickest movie villains from the ‘90s, John Doe (Kevin Spacy) in Seven is as mean as he is demented, which is a lot. The ritualistic killings inspired by the Seven Deadly Sins is one thing, and the massive collection of angry journal entries is another, but the way he says, “Oh, he didn’t know?” after the big plot twist is just so menacing.
Nino Brown (New Jack City)
Wesley Snipes played some great villains in the ‘90s, but his meanest has to be Nino Brown in New Jack City. While Simon Phoenix in Demolition Man is great, his character in the 1993 sci-fi flick is just so over-the-top and cartoonishly evil. Brown, on the other hand, is cold, methodical, and just a bad dude.
Kathryn Merteuil (Cruel Intentions)
The ‘90s were a great time for iconic movie villains, and of course, Kathryn Merteuil (Sarah Michelle Gellar) from Cruel Intentions is on that list. The games, the seduction, the toying with peoples' lives to the point where they are damaged beyond repair, and pretty much everything else she does in this 1999 staple is evil and mean-spirited.
Agatha Trunchbull (Matilda)
Roald Dahl had a way of creating legendary villains in his various stories, which is the case for Agatha Trunchbull (Pam Ferris) in Danny DeVito’s 1996 adaptation of Matilda. The olympian-turned-principal at Crunchem Hall makes life a walking nightmare for all the students, who she throws around, stuffs in tiny closets, and tries to embarrass in front of the entire school.
Debo (Friday)
There are few ‘90s movies villains that are as recognizable as Debo from Friday. Played by the late Tiny Lister, who also portrayed a big bad in the 1989 wrestling movie, No Holds Barred, this towering mountain of an antagonist was an absolute unit who preyed upon the smaller and weaker residents of his neighborhood. Well, until he got knocked out.
Captain Hook (Hook)
Steven Spielberg’s Hook is a movie that the internet seems to hate, but there are a lot of great things going for this 1991 retelling of Peter Pan. Robin Williams is great as the beloved Peter Pan character and Dustin Hoffman is a force of cartoonish evil in his portrayal of Captain Hook. The hooked hand, the wig, the turning Peter’s son against him, and that mustache put him at the top of the list.
Sheriff Of Nottingham (Robin Hood: Prince of Thieves)
Alan Rickman is mostly remembered for Hans Gruber in Die Hard, at least when it comes to movie villains. However, a few years later, the late Harry Potter star chewed up all the scenery with his portrayal of the Sheriff of Nottingham in 1991’s Robin Hood: Prince of Thieves. Kevin Costner is the star of this epic, but it’s Rickman, with his “I’ll cut your heart out with a spoon” line that steals the show.
Annie Wilkes (Misery)
Kathy Bates won an Oscar for her portrayal of Annie Wilkes in Misery, and rightfully so. The 1990 Stephen King adaptation helmed by Rob Reiner is one of the best horror movies of all time and features several of the most disturbing scenes imaginable. It’s Annie, despite her smile and infectious laugh, who is perpetrating all the madness. The hobbling scene alone makes her the meanest of the mean.
Percy Wetmore (The Green Mile)
Percy Wetmore (Dough Hutchison) in The Green Mile has to be one of the meanest, most sadistic characters from Stephen King’s catalog and one of the most hatable villains from the ‘90s. From intentionally botching an execution by the electric chair, trying to kill a mouse, and being a detestable human being in general, he did it all.
Max Shreck (Batman Returns)
Though Danny DeVito’s Oswald Cobblepot is supposed to be the villain in Batman Returns, it’s Christopher Walken’s Max Shreck who is the biggest jerk of Tim Burton’s 1992 comic book movie. He kills his secretary, is corrupt beyond belief, plans the kidnapping of the mayor’s child, and that’s just in the first act.
Peter And Paul (Funny Games)
Michael Haneke’s psychological horror film, Funny Games, features two of the most ruthless yet unassuming villains of the ‘90s with Paul (Arno Frisch) and Peter (Frank Giering), two young men who hold a family hostage and subject them to all kinds of torture. I mean, the “cat in the bag” game is one of the most disturbing scenes of all time.
Norman Stansfield (Leon: The Professional)
It’s impossible to talk about Gary Oldman’s best work without mentioning Norman Stansfield from Leon: The Professional and it’s just as impossible to discuss the meanest ‘90s movie villains without including his unhinged DEA agent. He’s psychotic, he’s ruthless, and most of all, he’s mean as a rattlesnake.
Judge Claude Frollo (The Hunchback Of Notre Dame)
Is there a Disney villain who is more unsavory, more unlikeable, or more disgusting than Judge Claude Frollo (Tony Jay) in 1996’s The Hunchback of Notre Dame? He’s sinister, slimy, and undeniably gross, but most of all, he’s unnecessarily mean to anyone and everyone around him.
Cyrus The Virus (Con Air)
Cyrus the Virus (John Malkovich) from Con Air is one of those movie villains that is just too awesome. Sure, he’s a terrible human being with little to no redeeming qualities, but that’s part of the charm of this convicted criminal and mastermind behind the movie’s big hijacking.
Warden Norton (The Shawshank Redemption)
Warden Norton (Bob Gunton) from The Shawshank Redemption has to be one of the most vile and meanest officials from any prison movie or TV show ever released (that includes Tommy Lee Jones’ warden in Natural Born Killers). For two-plus hours, this evil man makes life miserable for all the inmates with his self-serving ways. But yeah, he gets his comeuppance in the end.
Jean-Baptiste Emanuel Zorg (The Fifth Element)
Gary Oldman was on fire throughout the 1990s when it came to playing wild villains, and Jean-Baptiste Emanuel Zorg from The Fifth Element is high up on that list. He’s a violent arms dealer who’s working for the Ultimate Evil to get as much power and control as possible. Also, that haircut and fashion sense add a nice touch to his evil character.
Helen Sharp (Death Becomes Her)
Everyone is pretty much a villain in Death Becomes Her, but the character that stands out the most is Goldie Hawn’s Helen Sharp, who is as vindictive as she is charming and beautiful. Though her revenge against Ernest Menville (Bruce Willis) is somewhat justified, she takes things to the next level and then some.
Scar (The Lion King)
The Lion King has a lot of noble and friendly characters like Simba, Mufasa, Timon, and Pumbaa, but Scar (Jeremy Irons) doesn’t fall into either category. The jealous, vindictive, and cruel brother of the king goes to great lengths to take the throne, even killing his own sibling and blaming the death on his young nephew. Talk about a terrible uncle.
Castor Troy (Face/Off)
There are over-the-top Nicolas Cage characters and then there is Castor Troy from Face/Off. This dude starts wilding out and he doesn’t stop throughout the whole movie, and it’s better off for it. Dressing up like a priest, assaulting a girl, and later wearing the face of an FBI agent and living his life is just something wild.
The Wet Bandits (Home Alone)
Harry Lime (Joe Pesci) and Marv Murchins (Daniel Stern), known collectively as the Wet Bandits, are the big bads in Home Alone (though Uncle Frank isn’t far behind). But what makes them so mean is the fact that instead of just robbing people over Christmas, they flood their houses before leaving. So now they get robbed twice: by the Wet Bandits and the insurance company.
Aaron Stampler (Primal Fear)
The plot twist at the end of Primal Fear is a work of art and what makes it so great is Edward Norton’s performance. His transition from the meek and reserved Aaron Stampler to Roy is absolutely terrifying. But it’s not just the evil nature of the character or the vicious murder he committed, it’s the pleasure and joy he got out of the killing and court proceedings that makes it so devilishly fun to watch.
Phillip Stuckey (Pretty Woman)
In the realm of rom-com scumbags, Philip Stuckey (Jason Alexander) from Pretty Woman is in a league of his own. The greedy, power-hungry, and sleazy attorney to Richard Gere’s Edward Lewis. The way he puts down his client, the company he’s trying to buy, and worst of all, Vivian Ward (Julia Roberts) is mean and disgusting, to say the least.
Eric Gordon (Billy Madison)
Bradley Whitford plays a jerk better than just about anyone in Hollywood, and for many, the first time we saw him in action was in the 1995 Adam Sandler comedy, Billy Madison. In the movie, Whitford plays Eric Gordon, the executive vice president of Madison Hotels who tries and tries again to thwart Billy’s plan of finishing school and taking over the family business. Come on, manipulating a school principal and putting your secretary in a coma is next-level.
Ordell Robbie (Jackie Brown)
Three years after playing one of the most unforgettable characters of the ‘90s in Pulp Fiction, Samuel L. Jackson played one of the meanest villains with his take on Ordell Robbie in Jackie Brown. The arms dealer who gets Jackie Brown (Pam Grier) to smuggle money from Mexico to the United States has no limits throughout Quentin Tarntino’s crime epic. Both vile and violent, Ordell doesn’t mess around.
Caledon 'Cal' Hockley (Titanic)
A colossal movie like Titanic needs an even bigger villain, and Billy Zane did just that with his portrayal of Caledon “Cal” Hockley, Rose’s (Kate Winslet) uber-rich fiance. The way he carries himself, the tone in his voice, and that “looks too good to be a good guy” haircut makes him an all-time movie heel.
Tracy Flick (Election)
Reese Witherspoon has played some of the most beloved movie characters over the years, but she’s also played some downright awful villains. A perfect example is Tracy Flick from Election, Alexander Payne’s 1999 comedy about a student government presidential race. She’s successful and chipper, but she does some down-and-dirty and unethical stuff to get her way.
These movie villains are great in their own way, but they all have one thing in common: they’re mean beyond belief. Some are worse than others, but they all made the moviegoing experience in the ‘90s so much fun.
