The 100 Greatest ’90s Movie Characters (50-41)

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.

50. Dr. Evil (Mike Myers) | Austin Powers: International Man of Mystery (1997)

Mike Myers is untouchable. Say what you will about his career post-Shrek, but I still contend Myers is a once-in-a-generation talent. Not since Peter Sellers has anyone captured his ability to comedically portray numerous, ingenious characters to this degree and to that level of consistency. His dossier is packed with so many incredible characters it’s borderline ridiculous:

  • Wayne Campbell
  • Simon who likes to do drawings
  • Coffee Talk
  • Grumpy Old Man Stuart McKenzie
  • Dieter
  • Shrek
  • Austin Powers

Goodness. The man is next-level. But, for my money, Dr. Evil just might be his best creation. Perfectly meta; perfectly brilliant; perfectly absurd; perfectly nuanced to a ridiculous degree; perfectly random; and perfectly [almost] sinister. From the lexicon of Eve-ill catchphrases to the iconic art deco style grey suit, Dr. Evil didn’t just exist in a trilogy of peak parody comedy flicks — he vaulted into the stratosphere of pop cultural influence. The character is infamous and the legacy will live on long after the movies are remembered. This monologue alone, delivered at a Carrie Fischer led group therapy session, is enough to keep Dr. Evil in the comedy hall of fame. I just… I can’t quite put my finger on a definitive reason why other than to say, Myers’ Dr. Evil hit at just the right time and gave us just the right amount of homage-meets-parody and just the right amount of unpredictable zaniness that it simply hit. And boy was it a homerun. So let’s all place our pinkies to the corner of our mouths, share a sinister chuckle, dance a quirky jig or two, and demand billions of dollars. Because Dr. Evil showed us how.

– Mitch Roush

49. Sarah Connor (Linda Hamilton) | Terminator 2: Judgment Day (1991)

When we first met Sarah Connor in Terminator, she was a typical damsel in distress type. The entire plot revolves around John Connor sending back a friend, Kyle Reese, in time to save his mother from Schwarzenegger’s terminator. Although certainly not helpless by the end of the film, that is Sarah Connor’s role in the film — someone who must be saved. But she is far from helpless come the sequel. She starts the movie in a mental institution, raving about the impending end of the world. But she’s absolutely jacked and busts herself out while John and a reprogrammed version of Schwarzenegger’s terminator come to protect her. This starts the action hero narrative of Sarah Connor. Schwarzanegger plays a big role again here, but Hamilton owns the movie and that’s saying something.

– Jacob Holmes

48. Andy Dufresne (Tim Robbins) | The Shawshank Redemption (1994)

Personal development gurus like Tony Robbins have spent years studying successful people, and what they’ve figured out is that many of them share similar qualities. Vision is one of them. The ability to not only have a goal but to see one’s self accomplishing it in one’s mind, and to know that it is inevitable, is an ability many high achievers like Michael Jordan have in common. Patience and perseverance are two more. Knowing that to achieve a goal, one must delay gratification and push through in the face of obstacles is a trait that seems to mark the successful. 

While Andy’s success isn’t exactly what we’re thinking about when we are dreaming of becoming rich or famous or whatever it is we dream about, he embodies the traits of the highly successful in our society. It can be a challenge to convey the mindset of a character to an audience, but Tim Robbins’ far off gaze and dream-filled eyes tell us everything we need to know: Andy has a goal, he has a plan that he is patiently executing to attain the goal, and he can see it all working out perfectly in his mind’s eye. 

Unfortunately, I’m not naturally very much like Andy. I’m impatient and struggle to visualize the end game in detail when it comes to goals. But Andy Dufresne has been—and continues to be—an amazing example that I look to for inspiration when I feel like I am failing myself. I mean, none of my goals require me to crawl through a river of shit and piss. Which is nice. 

– Billy Dhalgren

47. Raoul Duke (Johnny Depp) | Fear and Loathing in Las Vegas (1998)

Hands down one of Johnny Depp’s best roles. Sure some of you will argue for his Pirate Keith Richards, but I’m sorry this one is better. By far. He is just so all over the place in this Terry Gilliam flick that you can’t help but get sucked in by him and all the craziness that ensues. Besides when you’ve got, “two bags of grass seventy-five pellets of mescaline, five sheets of high powered blotter acid, a salt shaker half full of cocaine, and a whole galaxy of multi-colored uppers, downers, screamers, laughers… and also a quart of tequila, a quart of rum, a case of Budweiser, a pint of raw ether and two dozen amyls.”, what could go wrong?

– K. Alvarez

46. Craig Jones (Ice Cube) and Smokey (Chris Tucker) | Friday (1995)

Craig is a decent guy with a stable family who can’t resist peer pressure. His pal Smokey is the loveable bad influence who’s trying to evade his murderous drug dealer. Together, they spend one long Friday sitting on a porch smoking away while trouble finds them over and over and over again. OK, they find some of the trouble without any help. But it’s Friday. You ain’t got shit to do and you know this maaaaaaaaaaaaan!

– Vincent Kane

45. Howard Payne (Dennis Hopper) | Speed (1994)

“Poor people are crazy, Jack. I’m eccentric.” Dennis Hopper, man. He had a varied and accomplished career, and yet it’s his villains I remember the most. From Frank Booth in Blue Velvet to Kaufman in Land of the Dead. In the 1990’s we got Deacon, the mad ruler of the Smokers in Waterworld and the mad, bad former bomb-squad detective Howard Payne in Speed. Payne is smart, vindictive and a psychopath – he’s willing to kill and maim just to get the money he thinks he’s owed. When his original plan to hold people in an elevator hostage is foiled by detectives Jack Traven (Keanu Reeves) and Harry Temple (Jeff Daniels) he quickly switches gears to include a little revenge in his terrorism.

If he was just crazy, Payne wouldn’t be that memorable a villain, but Dennis Hopper manages to infuse a charismatic mania and mean-spirited sense of humor into things. He’s always one step ahead of the good guys – until he isn’t. “I’m smarter than you, Jack!” he exclaims at one point, and he really is. Smarter, more vicious and more dedicated. He could have gotten away with it, if only he could have kept his ego in check. But what kind of fun would that have been? “Pop quiz hotshot. You can only pick one Dennis Hopper bad guy for the list. What do you do? WHAT DO YOU DO?”

– Bob Cram

44. Will Munny (Clint Eastwood) | Unforgiven (1992)

William Munny is Clint Eastwood doing his Clint Eastwood thing, but deconstructed as hell. Unforgiven is a phenomenal piece of work that deserves all the praise it receives. The best thing about it is that it uses the screen presence Clint Eastwood has, takes the edginess his characters have had in the past, but is really honest about what a character who is that violent and that ruthless could actually be like in reality. People out there taking lives left right and center would not necessarily discriminate, not necessarily be the heroic type that kills the “right” people and the right people only. A brilliant character study, and the crown jewel in Eastwood’s filmography.

– D.N. Williams

43. Dr. Ian Malcolm (Jeff Goldblum) | Jurassic Park (1993)

Out of all of the human characters in Jurassic Park, Dr. Ian Malcolm is arguably the most memorable. Jeff Goldblum brings a unique and humorous take on Dr. Malcolm, an expert in Chaos Theory whose purpose at Jurassic Park is to assess the facility. While a lot of the characters in the movie are fascinated by John Hammond’s achievements, Malcolm remains the voice of reason, even when his opinions are laced with sarcasm or humor.

Goldblum’s body language and stuttering line delivery help create a three-dimensional character that we can all laugh with and root for. Not to mention that he has what are probably the most quotable lines in the movie, one of which pretty much sums up the entire franchise: “Your scientists were so preoccupied with whether or not they could that they didn’t stop to think if they should.”

– Romona Comet

42. Amon Göth (Ralph Fiennes) | Schindler’s List (1993)

There’s no historical figure as universally reviled as that of the Nazi. They are the go-to word for absolute evil and for good reason. It’s a political party predicated on the complete and total annihilation of an entire race of people. It’s not easy finding a more repulsive group of individuals nor is it easy finding a better example of their vile beliefs than Amon Göth.

Based on the first Nazi to be charged with the crime of homicide and not just being a war criminal (his actions were so heinous, that they needed a new category), Amon Göth is the main antagonist in Schindler’s List and is easily the most detestable person in a film where some people lock other people in gas chambers. When he’s not torturing Jews or shooting at them from his balcony (which he did in real life), he’s complaining to Liam Neeson’s Oskar Schindler about the difficulties of his job. Which involves ordering a lot of barbed wire and posts. It wouldn’t even occur to him to mention the Jew killing because that’s the banality of evil. Killing human beings is just another mundane aspect of his job. Like taking out the trash or pulling weeds. Which makes it that much more terrifying.

– Vincent Kane

41. Daniel Hillard / Euphegenia Doubtfire (Robin Williams) | Mrs. Doubtfire (1993)

It’s hard to imagine anyone playing Mrs. Doubtfire but Robin Williams. Yet, both Warren Beatty and Tim Allen were reportedly wanted for the role before Williams was cast. To me, that’s crazy to think that this movie wasn’t built specifically as a vehicle for Williams’ talents. As voice artist Daniel Hillard, Williams is able to show off his wide range of voices, and when he puts on the hair and makeup and transforms into Mrs. Doubtfire, he becomes an entirely different person. Some actors have a hard time playing characters that aren’t just themselves, but when Williams was acting, I never once thought, “I’m watching Robin Williams on screen.” It was always Mrs. Doubtfire, the Genie, Armand Goldman, Peter Pan, Walter Finch, or Patch Adams I watching.

Mrs. Doubtfire was the first Robin Williams movie I ever saw as a child. (I mean, it could have been Aladdin, but, if it was, I doubt I recognized Williams as the voice of the Genie.) To this day, it is still the role I associate with the actor the most. Some people will argue this movie is a product of the ’90s and hasn’t aged well, but I disagree. This is a movie about divorce that is still relevant to children today. Mrs. Doubtfire isn’t afraid to drop the comedy bits and get serious to talk about the effects of divorce on children. I cannot recall a single movie growing up that ended with the main character telling kids to not blame themselves for their parents divorce, and that as long as “there’s love, dear… those are the ties that bind, and you’ll have a family in your heart, forever.”

But also, the movie is freakin’ funny. Just last week, my mind started replaying the scene in the restaurant where Daniel is telling his boss that the reason he’s wearing lipstick is because he ran into his ex and she couldn’t keep her hands off of him. This, of course, leads the boss to ask if his ex has a girlfriend for him to which Daniel replies, “Hey, it’s the nineties.” There are so many scenes from Mrs. Doubtfire that live rent free in my head and they all there because of Robin Williams’ performance. Thank god Tim Allen and Warren Beatty weren’t cast, because this was a role only Robin Williams could have pulled off. Okay, bye bye, poppet.

– Marmaduke Karlston

60-51 | 40-31

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!