The 100 Greatest ’90s Movie Characters (70-61)

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.

70. T-1000 (Robert Patrick) | Terminator 2: Judgment Day (1991)

I’d seen the original Terminator about a thousand times before Judgement Day was released and I remember thinking there was no way this skinny Robert Patrick guy could possibly stand up to Arnold Schwarzenegger. About the time they spring Sarah Connor from the institution and he chases them down on foot while they’re IN A CAR I was all in. I think I even yelled out “he’s on the car, he’s on the fucking car!” in the theater. Billy Idol was originally going to play the upgraded Terminator model – and I think that could have been interesting, in a more over-the-top sort of way – but Patrick was the perfect choice. He’s like a shark, all dead eyes and graceful killing power. That run, with his hands like blades, has been copied and made fun of a hundred times, but when I first saw it it was terrifying. He’s running full out and he doesn’t even look like he’s trying. He made Arnold seem outdated and outmatched, and the shape-changing special effects were groundbreaking. Arnold was great in both this and the first film, but whenever I hear that phrase “It can’t be reasoned with, it can’t be bargained with. It doesn’t feel pity of remorse or fear and it absolutely will not stop. Ever. Until you are dead.” it’s Robert Patrick’s metallic face I see in my head. The perfect killing machine.

– Bob Cram

69. Jack Dawson (Leonardo DiCaprio) and Rose DeWitt Bukater (Kate Winslet) | Titanic (1997)

Whenever I talk to someone about Titanic, more often than not I hear “Jack and Rose’s romance would have never have happened in real life…” due to their social and economical differences. Third-class passengers were only allowed limited access to various parts of the ship, after all, so it’s not likely that a woman of Rose’s stature would have ever come into contact with someone like Jack Dawson. But you know what?

I. Don’t. Care.

Titanic is a movie and I am one hundred percent willing to ignore realism for a forbidden, star-crossed romance. This movie catapulted Kate Winslet into stardom and triggered Leo-mania with an intensity of which I honestly don’t think we’ve seen since. Jack and Rose’s iconic romance has stood the test of time and also gave us the never-ending debate over whether or not there was enough room on the door for both of the lovers.

– Romona Comet

68. Stansfield (Gary Oldman) | Léon: The Professional (1994)

It would be easy to fill this entry with nothing but memes and gifs. You’ve seen them, you know them. “Everyone” is the most famous and for good reason. I don’t think any other actor has made more of a meal from a single word. Oldman is allowed to chew every inch of the scenery and he does so in the most spectacular way possible. It’s over the top, yes but it’s never cartoonish. Even when he’s at his most outrageous, he never loses menace.

He’s an actual threat. There have been a million corrupt cops in film and a couple even appeared on this list but none are as memorable or as dangerous as Stansfield.

– Vincent Kane

67. Henry Hill (Ray Liotta) | Goodfellas (1990)

I remember listening to Henry Hill call up Howard Stern all the time back in the day. It wasn’t always the funniest bits, but it was always entertaining. So I see why they picked Ray Liotta to play him. He’s perfect for the role. He plays all the personalities of a man losing his mind to drugs absolutely amazingly. This is the film Scorsese should have won the Oscar for. It’s a damn near perfect film.

– K. Alvarez

66. Dr. Gonzo (Benicio del Toro) | Fear and Loathing in Las Vegas (1998)

God damn is this movie a wild ride. Benicio del Toro as Dr. Gonzo is the perfect sidekick to Johnny Depp’s Hunter S. Thompson. There’s just so much going on in this film that it’s hard to pinpoint anything to describe the film. It really is like a live action acid trip. Every single time you watch it you catch some other weird thing happening in the background or even right in front of you. This is another one I think needs to be rewatched sometime soon.

– K. Alvarez

65. Jesse (Ethan Hawke) and Céline (Julie Delpy) | Before Sunrise (1995)

Oh, this movie. This trilogy. Primarily focused on the dialogue and the characters themselves, the Before Trilogy follows the relationship between lovers Jesse and Celine over the course of about 18 years. While the sequels, Before Sunset and Before Midnight, are fantastic films in their own right, there is truly something special about Before Sunrise. Jesse and Celine meet on a train in Europe and disembark in Vienna to spend the day together. Watching Julie Delpy and Ethan Hawke fall in love over the course of one day is a sight to behold thanks to their talent and chemistry. Even the subtle glances are effective in squeezing your heart. Jesse and Celine’s romance is so nuanced but it’s presented so simply. It’s one of the few believable, realistic relationships in film and you immediately crave more as soon as the credit starts to roll.

– Romona Comet

64. Ellis Boyd “Red” Redding (Morgan Freeman) | The Shawshank Redemption (1994)

I went through all sorts of wanky analytical approaches to Morgan Freeman’s iconic character in my mind before I said fuck that shit and decided to just tell you how I feel about him: I like Red. 

Now, that may not be deep or epic, but I think it’s a huge reason why the movie works in the first place. I like Red. You like Red. We all like Red. We want Red to get out of Shawshank. We don’t want to see him hang himself like Brooks does. We want him to make it to that beach you can’t pronounce and be reunited with his friend Andy. We want him to live happily ever after. (Come to think of it, The Shawshank Redemption is kind of a love story in its own way, isn’t it?)

And why? 

Because Morgan Freeman could charm the claws off a hungry lion. He’s perfect for the role, and even though Tim Robbins turns in a wonderfully subdued performance, there’s no way this movie sees the success with audiences that it eventually saw in syndication. And that is why Red makes this list. 

– Billy Dhalgren

63. Selina Kyle / Catwoman (Michelle Pfeiffer) | Batman Returns (1992)

HOT TAKE: Pfeiffer’s Catwoman is a Top Five All-Time Comic Book Movie Performance.

HOTTER TAKE: And she deserved an Oscar nom.

I’ve made my love for Batman Returns known before. As far as I’m concerned, it’s a deliciously gothic yet intentionally subversive masterpiece. At least as far as comic book flicks are concerned. Why? To be quite honest… because Pfeiffer anchors the whole thing. I mean, just watch this segment and tell me it wasn’t perfect casting. I defy anyone to conjure up another red carpet A-list star that could’ve pulled off this impeccable channeling of “camp as high art meets sort of surprising gothic realism.” It can’t be done. Michelle Pfeiffer as Catwoman is as tried and true and — yes — iconic as anything the modern zeitgeist has seen. It’s time we gave her and this take on the popular character its due. Catwoman in all that early ’90s glory for the win!

– Mitch Roush

62. Dr. Sean Maguire (Robin Williams) | Good Will Hunting (1997)

In Good Will Hunting, Robin Williams showed us once again his talent and range as an actor. As Will Hunting’s court-ordered therapist Sean Maguire, William’s performance was a particularly special one. While he works to get his patient to open up and confront his demons, Maguire finds himself having to face and overcome his own. Every remarkable trait that made Williams such an outstanding actor is on display in this film. His humor and tenderness, not to mention his ability to tap into some dark emotions. This seems to have become more of a tribute to Robin than the character but to me, there is so much of Robin in this role. It may not be his most memorable role to some, but it’s certainly one of his best.

– Romona Comet

61. Catherine Tramell (Sharon Stone) | Basic Instinct (1992)

I tried very hard not to make this blurb about Sharon Stone’s vagina, but everything I wrote seemed…like I was trying not to make this blurb about Sharon Stone’s vagina. So here we are. 

When Basic Instinct came out in 1992, I was 16. I’m not saying I watched Basic Instinct for the first time because of the vag flash scene, but I probably watched Basic Instinct for the first time because of the vag flash scene. But, if memory serves, this was playing on repeat on Showtime, and somewhere along the way I just came to love this movie

Stone’s Tramell is iconic partly because of the controversy surrounding that famous scene, but the way Stone plays the character so coolly, so mysteriously, and so seductively is why I think she endures. Tramell is an updated femme fatale, and we’ve seen femme fatales in film a million times. But what makes this iteration of the trope memorable is Stone’s performance. And it’s why this character is one of the 90s best.

– Billy Dhalgren

80-71 | 60-51

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!