The 100 Greatest ’90s Movie Characters (30-21)

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.

30. Lloyd Christmas (Jim Carrey) and Harry Dunne (Jeff Daniels) | Dumb and Dumber (1994)

How can one describe Lloyd Christmas and Harry Dunne? They are ridiculous, insane, immature, and dare I say stupid individuals. Lloyd meets and falls for a beautiful woman, who leaves Rhode Island for Colorado, add Harry and let the buddy road trip commence! Yeah, that’s a pretty simplistic summary, but that’s all you need to know; that and there’s a kidnapping mystery rolled into it. Most films provide a maturity of the main characters, they learn something in the end. This is not the case. Harry and Lloyd do not change much over the course of the film and there is barely a nod to their backstories. What you have is a pure comedy that never takes itself seriously and tackles many taboo situations with hilarious results. Harry and Lloyd provide some of the most wet-your-pants funny moments in film since Leslie Nielsen and Robert Hays in Airplane! Who hasn’t been sent to the store with a list of items and been told “Just the essentials”?

– Ralph Hosch

29. Cole Sear (Haley Joel Osment) | The Sixth Sense (1999)

Cole Sear sees dead people, and it’s really messed him up. He’s bullied at school, his Mom isn’t sure how to help him and his new therapist has issues of his own. Haley Joel Osment manages to infuse the eight year old Cole with misery, sweetness and a world-weary outlook that would be more appropriate in someone decades older. This is a boy that lives in fear all the time – fear of the living, fear of the dead, fear that his mother will leave him and fear that there’s no relief from the unrelenting nightmare his life has become. That he manages, in the face of all of this horror, to care for others and try and help them is a measure of how big his heart is, and how great a character he has – and is. Bruce Willis’ Malcom Crowe is the nominal protagonist of The Sixth Sense, but Cole is the soul of the film and the reason I’m happy to rewatch it, even though I know the “twist.”

– Bob Cram

28. Kevin McCallister (Macaulay Culkin) | Home Alone (1990)

Who knew watching an eight-year-old brutally attack a couple of robbers could be so enjoyable?

Home Alone is a Christmas classic. This means two things: 1) that TV channels play it non-stop during December, and 2) because of this, I have no clue when I first saw Home Alone (but I do know it was when I was younger). The older you get, the more unrealistic you realize Home Alone is. As a kid, of course you’re going to believe the Wet Bandits could survive all the torture Kevin threw at them. But as an adult, you quickly realize that Kevin killed them both about eight times over. I don’t care what the new Home Alone movie hints at, there is no way Kevin didn’t grow up to be a psychopath (or at the very least, require hours and hours of counselling).

Despite these flaws, Home Alone remains an annual holiday watch for me and that’s mostly because of Culkin’s performance as the rambunctious and cheeky Kevin. I truly believe that he was the last child star. When you think of successful child actors, your mind immediately jumps to Shirley Temple and Macaulay Culkin. Nowadays, who do we have that had the same draw they did? The Stranger Things kids might come close, but—aside from Millie Bobby Brown—none of them have that pure talent Culkin has on full display in the Home Alone films. There’s a reason all the Home Alone films after Home Alone 2 failed. None of the child actors could even come close to matching what Culkin put into Kevin. It’s harder than it looks, and no one did it better than Macaulay Culkin.

– Marmaduke Karlston

27. Austin Powers (Mike Myers) | Austin Powers: International Man of Mystery (1997)

An inescapable pop culture phenomenon, the international man of mystery himself. There’s a certain breed of comedy character that seems to be more and more on the decline, or maybe they were always relatively rare. Your Ace Venturas, your Derek Zoolanders, your Ron Burgundys, your Borats. Austin Powers is definitely of a piece with those. An inescapable pop culture phenomenon that had the James Bond franchise itself running scared, the character might be appearing on a ’90s list, but he’s a ’60s character, or at least a ’60s character through a ’90s lens. Mike Myers, having been raised on ’60s Brit flicks by immigrant parents, lampoons the period with a significant degree of affection. Considering the kind of topics the character it touches on, and the kind of humour that the movie relies on, it’s aged particularly well.

– D.N. Williams

26. Annie Wilkes (Kathy Bates) | Misery (1990)

I find Stephen King to be a mixed bag as an author. He has high-highs and low-lows in his bibliography. His books are either heralded as classics or quickly forgotten about (his adaptations also suffer the same fate). But whether you love him or hate him, you have to admit that the man knows how to write compelling (and sometimes downright scary) characters.

Annie Wilkes is every writer’s worst nightmare. She claims to be Paul Sheldon’s #1 fan, but turns against him as soon as she finds out he has killed off Misery, the main character in his best-selling series of novels. She burns the manuscript for his next book, and forces him to write Misery’s Return, a book that will bring the Misery character back to life. Her actions continue to become more vicious as the film progresses (I think we all remember THAT SCENE) forcing Paul to take a stand for the sake of his life and work.

Despite the book coming out in 1987 and the film in 1990, it’s hard not to read/see Annie Wilkes as an embodiment of toxic fandom. She loves Paul Sheldon until he writes something she hates. In retaliation, she makes sure his next book is a failure (by burning it), and then believes she can instruct Paul on how to write a better Misery book. That’s pretty much what goes on nowadays online when “fans” of a particular series start to turn against the creatives. I’ll admit the word “toxic” gets thrown around too hastily these days, but, if I was asked to describe toxic fandom, I’d just say, “Go watch Kathy Bates’ performance as Annie in Misery. Then you’ll understand.”

– Marmaduke Karlston

25. Vivian Ward (Julia Roberts) | Pretty Woman (1990)

“Big mistake. Big. Huge. I have to go shopping now.”

One of the most iconic movies in rom-com history, Pretty Woman catapulted Julia Roberts into stardom with her role as Vivian Ward, the sex worker with a heart of gold. Opinionated and outspoken, Vivian was never afraid to go after what she wanted, so it was really no surprise when she won Richard Gere’s heart. Ask anyone about this movie and they’ll likely remember two iconic moments – the revenge shopping trip where she gets to tell off the two snotty store clerks who had previously shamed her for her less than elegant clothing choices, and the necklace box snap, where the world was introduced to Julia’s joyfully contagious laughter. Vivian is still one of more complex, interesting leads in any romantic comedy past or present and it’s hard to imagine anyone else but Julia Roberts starring in the role.

– Romona Comet

24. Jackie Brown (Pam Grier) | Jackie Brown (1997)

It was a calculated move on Tarantino’s part to do, what he refers to as “his comeback movie”, before he needed to comeback. Older directors tend to have one last mature work before dying and he decided to make his his third movie. Since it’s not Reservoir Dogs or Pulp Fiction, it wasn’t as warmly received at the time, but many consider it one of his best now. A good reason for that is the fact it feels “real.” Jackie Brown isn’t a comic book character like The Bride nor is she on some epic quest to kill Hitler. Her actions won’t rewrite history or even be remembered after a month. All she wants to do, is outsmart a dangerous gunrunner, make a little scratch and do it without dying or ending up in prison. Because she’s based on a character originally created by Elmore Leonard, she was badass before Tarantino got her but the casting of Pam Grier (the character was originally white) added another level of reality and badass-ness. Because she’s a middle aged black woman clinging to her terrible job, you immediately understand her desperation but since she’s played by the queen of blaxploitation, you also know she’s gonna get it done. It’s a gift for an actress like Grier and her Oscar snub still stings all these years later.

– Sailor Monsoon

23. Doc Holliday (Val Kilmer) | Tombstone (1993)

An alcoholic, womanizing, compulsive gambler, suffering from a debilitating illness might not sound that heroic. But Val Kilmer’s Doc Holliday has to be one of the coolest characters to ever appear in a western movie. And that’s quite a high bar, considering all the badasses the genre has seen. A skilled gunslinger and the best shot in the west, he is the stand-out character in Tombstone. Teaming up with Kurt Russell’s Wyatt Earp, they take down the dastardly outlaws and look great in doing so. It all culminates in his epic final showdown with Johnny Ringo, where he once again gives us his iconic line, ‘I’ll be your Huckleberry’. If that doesn’t make you punch the air in delight, nothing will.

– Lee McCutcheon

22. Mr. Blonde (Michael Madsen) | Reservoir Dogs (1992)

Think of Reservoir Dogs and you probably think of that one scene. A razor blade, an ear, Stuck in the Middle with You, and of course a psychotic Mr. Blonde. He plays a bigger part in the overall film but the way he casually tortures and dismembers the helpless police officer during that particular scene will always stick with me. He’s a cool guy but not the type of cool guy you want to be friends with. And definitely not one you want to be enemies with. He is the one who helps events spiral out of control as he gleefully starts a shooting spree during the bank heist. The brother of Vincent Vega from Pulp Fiction, it’s clear Mr. Blonde is the one who got the evil genes. 

– Lee McCutcheon

21. Dante Hicks (Brian O’Halloran) and Randal Graves (Jeff Anderson) | Clerks (1994)

The two of these unknown actors hired by Kevin Smith for his first film are a goddamn hilarious duo if there ever was one. Their trivial and mundane conversations about life, love and cinema is everything we strive to be here at SAW. I love this relatable pair of blue collar shop keeps so much because in ’94 I was one of these blue collar shop keeps. And deep down inside I will always be one of them.

– K. Alvarez

40-31 | 20-11

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!