The 100 Greatest ’90s Movie Characters (90-81)

There has never been a decade in film quite like the ’90s. It was a time where foreign and independent films were as big as blockbusters. Unlike today where Disney has a monopoly on entertainment, it felt like cinema at that time was one giant sandbox where everyone could play. Auteurs from decades past were making movies alongside indie darlings. Hell, even documentaries were big. It was a fertile period for cinephiles and with that came a wellspring of iconic characters. There was bullet dodging hacker ninjas and Bible quoting hitmen. Charismatic cannibals, Scottish junkies, philosophical slackers and clerks who weren’t supposed to be here today. They made us start fight clubs, believe in ghosts and quote shagadelic spies ad nauseum. These are the characters that made the decade as beloved as it is.

These are the 100 Greatest ’90s Characters of All Time.

90. The Lieutenant (Harvey Keitel) | Bad Lieutenant (1992)

Keitel plays the corrupt and vile title character in this Abel Ferrara neo-noir drama. As a police officer who uses his status to exploit vulnerable women and abuse drugs, there is nothing redeemable about the Lieutenant’s choices, and they all come crashing down upon him after he investigates the sexual assault of a nun.

Keitel manages to give depth and dimension to a man whose crimes and indiscretions are unjustifiable, adding nuance to the film’s exploration of good and evil. Keitel’s frequent collaborator Martin Scorsese considers Bad Lieutenant the best film of the 1990s.

– Vincent Kane

89. The Lisbon Sisters | The Virgin Suicides (1999)

Based on the novel of the same name by author Jeffrey Eugenides, The Virgin Suicides tells the story of five sisters who, due to their over protective family, become isolated and shut off from the outside world and because of this, become more and more despondent. After the youngest one, Celia (Hanna R. Hall), tries to kill herself, the rest of the sisters are put under house arrest. Due to their beauty, they become the object of desire of the local boys but since none of them can get close to them, they’re all shrouded in mystery. They almost become a suburban myth — the unattainable Lisbon Sisters, but within the house, their lives are anything but a fairy tale.

Watching these girls, Lux (Kirsten Dunst), Mary (A. J. Cook), Therese (Leslie Hayman), Bonnie (Chelse Swain) and Cecilia slowly have the life and happiness drain from their lives, is a tragedy on the level of Shakespeare. Sofia Coppola’s directorial debut is kind of like the anti-teen film. There’s no cliché meet cute or inspirational feel good vibe, it’s a film who’s title let’s you know going in what the tone will be and it ain’t no bait and switch. It’s an emotionally devastating portrait of teen angst and desperation made unforgettable by five amazing performances.

Sailor Monsoon

88. Mike Peters (Jon Favreau) and Trent Walker (Vince Vaughn) | Swingers (1996)

If you were in the dating scene in the late nineties you’d be hard pressed to not be able to identify with Mike Peters (John Favreau), a struggling actor just getting out of a long-term relationship, and his friend Trent Walker (Vince Vaughn), who helps Mike get back into the dating scene. The film itself is a snapshot of the Los Angeles party/dating scene of the ’90s, but the interaction between Mike, Trent and their friends really makes the movie go. As well It should, because Favreau wrote the script and based the characters off of his own experiences in LA. The real-life friendship between Favreau and Vaughn shines through in their portrayals of Mike and Trent. Trent’s lecture to Mike about being a bear on the dating scene is classic Vince Vaughn. This is essentially a buddy movie of the highest level, shot on a shoe string budget. Personally, every guy has been a love-sick Mike and everyone knows a “fearless” Trent and that’s the key to this movie.

– Ralph Hosch

87. Bodhi (Patrick Swayze) | Point Break (1991)

Patrick Swayze’s Bodhi in Point Break is less a character than he is an idea or concept. Or one half of a concept. Keanu Reeves’ Johnny Utah being the other half. Together, these two characters represent the struggle between the id and the superego. The ever-present tension between order and chaos. 

As a character, Bodhi is a flawed human, maybe even a maladapted one. He represents one extreme—a challenge to the social order, to conformity, mediocrity and boredom—while Utah represents the extreme at the other end of the order-chaos spectrum—The System. 

But by the end of the film, Reeves’ Utah has been pulled toward the middle. His character has grown while Bodhi has…nah, man, I’m just joshin’. Bodhi is just a super bad ass mofo who rides big ass waves, jumps out of airplanes, takes what he wants, and gets the chicks.

What could be more memorable than that?

– Billy Dhalgren

86. William Wallace (Mel Gibson) | Braveheart (1995)

When Mel Gibson’s Braveheart came out in 1995, it quenched a thirst for gritty medieval European historical films that hadn’t been quenched since John Boorman’s Excalibur set the bar for gritty medieval European historical films over a decade before. A quarter century on, the movie about the Scottish national hero hasn’t aged quite as gracefully as Boorman’s classic, but it’s still damned entertaining. As director and star, Gibson gets much of the credit for the film’s status as a classic. 

As a character, William Wallace isn’t particularly original. He’s the classic hero trope, but Gibson’s natural charisma and clear vision as a storyteller elevates what could have been a stale rehash of stories we’ve seen a million times to something that is so viscerally entertaining we can’t help but suspend our disbelief, look past the historical inaccuracies and get swept along in the drama. 

Via Gibson, William Wallace emerges from history as a little-known regional hero to an internationally-recognized symbol for freedom and justice. All without shooting fireballs from his eyes and lightning bolts from his arse. (Which would have been pretty cool, by the way.) 

– Billy Dhalgren

85. Mickey (Woody Harrelson) and Mallory Wilson Knox (Juliette Lewis) | Natural Born Killers (1994)

When you talk about chemistry between two actors I doubt there’s a better example than Woody Harrelson and Juliette Lewis. Their characters Mickey and Mallory Knox are embroiled in a scarily passionate relationship. Both coming from abusive backgrounds, they find their perfect match in each other. This isn’t necessarily a positive thing for the rest of the world as they help each other justify their heinous actions. It’s not all smooth sailing for the loved-up couple though. You get the feeling they could either make love to each other or kill each other at any moment. And that makes them absolutely impossible to take your eyes off. 

– Lee McCutcheon

84. Tre Styles (Cuba Gooding Jr.) | Boyz n the Hood (1991)

It’s hard to think of a 90s film where I’ve wanted a character to achieve their goals more than Tre Styles in Boyz n the Hood. He is the stereotypical example of a good guy being brought up in the wrong surroundings. But when it’s done as well as it is in this film it doesn’t matter that we’ve seen that journey before. As he tries to break free from what seems like the inevitable path set out for him, you can’t help but will him on with everything you have. Probably the high point in Cuba Gooding Jr’s career and looking back at this performance it’s all the more disappointing he never fulfilled his potential. 

– Lee McCutcheon

83. John Coffey (Michael Clarke Duncan) | The Green Mile (1999)

I read the original serial novel of The Green Mile as it came out. I remember enjoying it, but also feeling like the pacing was weird. Off. I don’t think I’ve read it since then, but I’ve seen the Frank Darabont adaptation a couple of times. The pacing of the film is off as well, for me, it’s too languid, almost to the point of losing my interest. Every time Michael Clarke Duncan is on screen, though, I’m riveted. I would never have cast him – I think I only knew him as minor heavies and from Armageddon when the film came out – but he’s astonishing in the role. He radiates love and anguish in equal measure. He seems possessed of something unearthly, but rooted in kindness. Part of that is down to how the film uses him, but most of it is the actor and the role and a combination that lifted them both. Duncan had a successful career in part due to this role, and he was good in everything, but John Coffey was his best role, and when I think of him I always hear his voice. “I’m tired, boss. Mostly I’m tired of people being ugly to each other.” Me too, John. Me too.

– Bob Cram

82. Agent Smith (Hugo Weaving) | The Matrix (1999)

The Matrix Resurrections will be with us very, very shortly, and while we may be excited, there are two things we know for sure (or at least feel fairly safe assuming) are going to be missing from that film. One of them, which has been remarked upon repeatedly, is Laurence Fishburne. It makes sense that the absence of Laurence Fishburne has been a hot topic, because he has been replaced in some capacity by Yahya Abdul Mateen II.

However, we’re not going to be getting any Hugo Weaving either, and that’s just as important. Sure, there are a bunch of agents around, and we’re used to seeing other agents being part of the story, but it goes without saying that Hugo Weaving’s Agent Smith contributed considerably to the tone and feeling of the original Matrix movie. His absence will be keenly felt. He stormed onto the scene with one of the most indelible villain performances in film history, snarling and aloof, somehow selling “boring” and “generic” with absolute menace and a vital distinctiveness simultaneously. Every arch of his eyebrow and every curl of his lip was instrumental in establishing the film’s tone.

– D.N. Williams

91. Drexl Spivey (Gary Oldman) | True Romance (1993)

I thank the cinema gods that True Romance was made in 1993 and not anywhere near today or we wouldn’t have received the blessing of Gary Oldman playing a racially confused pimp with dreadlocks. He’s only in two scenes but that is all Gary Oldman needed to completely transform into an iconic character that you don’t forget. Tony Scott simply told Gary that he would be playing a white pimp who thinks he is black and Gary simply said that was all he needed to hear before taking the part. He would completely immerse himself into this controversial role where he is pretty unrecognizable. “It ain’t white boy day, is it?”

-Vincent Kane

100-91 | 80-71

What do you think of the selection so far? Who are some of your favorite ’90s characters? Maybe they will show up further on the list!