The 100 Greatest ’90s Movie Characters (100-91)

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.

100. Jimmy Jump (Laurence Fishburne) | King of New York (1990)

Laurence Fishburne’s performance as Jimmy Jump never gets the credit it deserves for being one of the first and best hip hop characters in film. Chalked full with gold chains, gold teeth, and dressed in black, Fishburne is a textbook hood and dominates every scene that he’s in, beginning with his first appearance at a fraught drug deal in a posh hotel. He harries the chemist (a young Steve Buscemi) into giving him a sample of the goods, talks rapidly and incessantly, and finally presents a Hispanic coke-peddler with a suitcase full of tampons to plug the bullet holes he’s about to fill him with.

Fishburne plays Jump with such manic intensity that it’s hard to shake him from your mind after the credits roll. Even on the verge of death, he cackles ghoulishly and wriggles around. A stunning performance from an actor at the very top of his game.

– Vincent Kane

99. Curly Washburn (Jack Palance) | City Slickers (1991)

Old, cranky, crusty, tough as nails; those words typify Jack Palance’s portrayal of Curly Washburn in City Slickers. As the leader of the cattle train from New Mexico to Colorado, Curly often is at odds with the “soft, pampered yuppie” participants (Billy Crystal, Bruno Kirby and Daniel Stern); often attacking them with his acidic quips in a hysterical delivery. In the end, it’s a learning experience in friendship and teamwork taught by Curly and the trials and tribulations of the American West. Despite Curly’s mildy antagonistic approach, his passing near the end of the film is a gut punch. I would be remiss if I did not state that Palance won the Academy Award for Best Supporting Actor for his portrayal of Curly and yes, he’s that good. The character was such a favorite, Palance returned from the dead (there’s a gag in the film) to portray Curly’s brother Duke in the sequel.

– Ralph Hosch

98. Billy Doyle (Woody Harrelson) and Sidney Deane (Wesley Snipes) | White Men Can’t Jump (1992)

One is a trash-talking, flashy street baller that does hard damn work to look pretty and the other is a dorky, fundamentally sound ball player who can’t dunk. What do these two have in common? They are both hustlers and make one hell of a team. Woody Harrelson’s peanut butter to Welsey Snipes’ jam creates one of the best duo’s of the 90s. Their chemistry made what could have been an average basketball movie into an instant classic that entered pop culture and still finds relevance today.

– Vincent Kane

97. Alexander Dane (Alan Rickman) | Galaxy Quest (1999)

That’s SIR Alexander Dane, by the way. A serious, Shakespearean acTOR (he played Richard the Third on stage you know, with FIVE curtain calls) Dane is frustrated, angry and resentful of being typecast by his most famous role – that of Dr. Lazarus on the classic sci-fi TV Show Galaxy Quest. While Dane is more resistant to embracing his character’s legacy than other members of the cast, he’s also the one most touched by the devotion of the alien Thermians – particularly Quellek. While the character could easily have been a one-note parody of any number of genre actors, Alan Rickman plays the part with gusto and heart, managing to turn a bitter, has-been actor into a hero worthy of his character. By Grabthar’s Hammer, what a role.

– Bob Cram

96. Daniel Robitaille / Candyman (Tony Todd) | Candyman (1992)

A monster born from a myth, a myth born from racial injustice, Candyman is Bloody Mary for the 20th century. Clive Barker’s other famous creation, Candyman will forever live in the shadow of Pinhead and the cenobites, which is a shame considering his mythology is far more interesting. Starting life as an accomplished painter who committed the greatest sin of the time (falling in love with a white woman), he was eventually captured and tortured to death. His captors turned his ass into a figurative honey baked ham in order to get ants to eat him alive. They also replaced his hand with a hook. I have no idea why but that’s pretty fucking cool. Freddy was a child killer (who might’ve been a pedophile) who was burned alive, Jason was a momma’s boy who couldn’t swim but Candyman was eaten alive by fucking ants. That’s an origin so tragic, you kind of sympathize with him and with Tony Todd playing him, you almost fall in love with him. Be his victim.

– Sailor Monsoon

95. El Mariachi (Antonio Banderas) | Desperado (1995)

One of the coolest and sexiest characters of the 90s. El Mariachi was one of those characters that women wanted and men wanted to be like. He could sing, play the guitar, get the girl and shoot a bunch of henchmen all at the same time like no one else. Antonio Banderas would enter the Hall of Fame of action heroes with this one performance for how badass he was. Also, because he banged Selma Hayek. Bravo sir.

– Vincent Kane

94. Jay and Silent Bob (Jason Mewes and Kevin Smith) | Clerks (1994)

“Noisenoisenoise, smokin’ weed, smokin’ weed, doin’ coke, drinkin’ beers.”

This iconic 90s duo is the R2-D2 and C-3P0 of the View Askewniverse. Inspired by the real life 18/19 year old Jason Mewes, Kevin Smith created on of the best stoner duos of all time. Right up there with Cheech & Chong if you ask me. Their on screen chemistry is fantastic and Jay’s nonsensical diatribes make you laugh every time.

“Pack o’ wraps, my good man, it’s time to kick back, drink some beers and smoke some weed.”

– K. Alvarez

93. The Iron Giant (Vin Diesel) | The Iron Giant (1999)

The Iron Giant shouldn’t work. He hardly speaks throughout the film. And yet, so much is communicated through his relationship with Hogarth Hughes. One minute he’s accidentally eating Dean’s scrap metal art or making a giant splash in the local pond, the next he’s having deep meditations on death and purpose. It’s fitting when he sees the “atomic menace” Atomo comic that he sees himself on the outside, but when he sees Superman he sees himself on the inside. By the time he utters “Superman” and shuts his eyes you can’t help but be torn to pieces at his sacrifice. He is a reminder to us all that we are who we choose to be. You choose.

– Jacob Holmes

92. Heather Donahue, Michael C. Williams, and Joshua Leonard (Themselves) | The Blair Witch Project (1999)

There are people who, to this day, believe that Heather Donahue, Michael C. Williams, and Joshua Leonard are actors who have been hired to portray the REAL Heather, Mike and Josh. They think The Blair Witch Project really happened, and that those kids actually disappeared. Can you imagine that? Having to be confronted by people who don’t think you’re who you say you are just because you played a role too well? When the three young actors auditioned for Eduardo Sanchez and Daniel Myrick’s found footage breakthrough film they had no idea what they were in for. Not just in the making of the film, which was physically and emotionally grueling, but also in the aftermath when Artisan Entertainment ran with the concept of the film being real and launched one of the first viral marketing campaigns in history. A lot of people have denigrated the acting in the film, but I think Heather, Mike and Josh do a fantastic job of portraying heightened versions of themselves in a difficult situation. Their confusion, frustration, distress, and fear feel real – and if they hadn’t done such a good job no one would have bought the concept. As it is, some people have bought into it far too much.

– Bob Cram

91. Stifler (Seann William Scott) | American Pie (1999)

Growing up, we all had a friend like Stifler (or one that tried acting like him). The guy who was immature and childish, but still managed to be a total chick magnet. Stifler doesn’t factor into the main plot of American Pie; instead, his purpose is to provide the audience with some comedic relief. This sometimes comes at his own expense (just how was the pale ale, Stifler?). The character doesn’t do much growing over the course of the franchise, but he doesn’t have to. By remaining a static character, Stifler shows just how much his friends have matured through American Pie (and its sequels). He’s the perfect supporting character for Jim, Kevin, Oz, and Finch. And while he may not have an iconic catchphrase like “This one time, at band camp…”, he’s the fan favorite in a franchise with a number of standout characters. Stifler has left his mark on pop culture simply by being himself. That’s the moral of this write-up, screenagers. Be yourself. (But being the life of the party doesn’t hurt either.)

– Marmaduke Karlston


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!