The 100 Greatest ’90s Movie Characters (40-31)

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.

40. Phil Connors (Bill Murray) | Groundhog Day (1993)

“You want a prediction about the weather, you’re asking the wrong Phil. I’ll give you a winter prediction: It’s gonna be cold, it’s gonna be grey, and it’s gonna last you for the rest of your life.”

Bill Murray has had a very long career full of memorable characters. But for me, one of his best performances is that of Phil Connors, the arrogant, self-serving weatherman sent to Punxsutawney to cover Groundhog Day. Suddenly finding himself in a time-loop, reliving the same day over and over again, Phil goes through a bevy of emotions, some of which can get pretty dark. Phil is not meant to be a likable character and for me, Murray was the perfect choice for the role. He has the ability to be smug and smarmy, but also weirdly charming at the same time. You can’t help but laugh at his pain while also sympathizing and truly wanting to see him change for the better. A lot of movies have followed the Groundhog Day formula of this movie, but very few even come close to capturing its heart and sharp comedic wit… probably because they didn’t have any character as memorable as Phil Connors.

– Romona Comet

39. Timon and Pumbaa (Nathan Lane and Ernie Sabella) | The Lion King (1994)

The best sidekicks in the Disney animated canon. These are iconic voices that literally shaped an entire generation. That speaks to the power of Shakespeare as much as it does the animated prowess of Disney in the nineties. On paper it sounds wild. Hamlet for kids, but with lions? Yeah, sure.

Well, turns out it was perfect. The Lion King is an all-timer in every sense of the phrase. Among the multitude of reasons why this lasting classic remains more profound than most any of its ilk are the arrival of our Timon & Pumbaa, or Rosencrantz and Guildenstern if you will. Nathan Lane brings his unmatched kinetic energy and turns it up full force. Ernie Sabella captures the perfect energy of humorously naïve to be the consummate sidekick’s sidekick. Together, the two gift “Hakuna Matata” and kick-off “Can You Feel the Love Tonight?” And they deliver the best hula ever performed for a pack of hungry hyenas cinema has every seen. Truly, an unmatched duo. Timon and Pumbaa are our life long beloved best friends. And I’ll still feel the same way when I’m 98 and humming “Hakuna Matata” to myself in my wheelchair, gumming tapioca pudding and rambling about how ’90s Disney was peak animation.

– Mitch Roush

38. Forrest Gump (Tom Hanks) | Forrest Gump (1994)

“My mama always said, ‘Life was like a box of chocolates. You never know what you’re gonna get.'”

I know a lot has been said about Forrest Gump the movie, but I think the reason Forrest Gump the character has endured as a piece of pop culture is because he’s an embodiment of chance. Numerous once-in-a-lifetime chances cross Forrest’s path and he never has any doubt in his mind to not take them. Play football? Sure. Go to Vietnam? Okay. Start a shrimping business? Why not. Become a ping-pong champion? Cool. Over the span of twenty-five years, he encounters many historical figures and events throughout his life. He takes any obstacle or opportunity thrown his way and is willing to make the best of the situation.

In many ways, Forrest’s story is also a representation of his “box of chocolates” quote. While watching Forrest Gump, you never did know who or what was going to cross paths with Forrest. And like any box of chocolates, some are better than others. But Forrest took them all in stride, whether they were good or coconut filled bad. I guess, it’s nice to watch Forrest Gump and remember that sometimes it’s worth it to take a chance on something that might feel new or scary. It’s like Mama always said, no one knows their own destiny; it’s something that we all have to figure out for ourselves. So get running and go find it.

– Marmaduke Karlston

37. Mona Lisa Vito (Marisa Tomei) | My Cousin Vinny (1992)

The hair. The fashion. The sunglasses. The monologues. The attitude. And this scene.

To say Marisa Tomei’s turn as Mona Lisa Vito is a force to be reckoned with is perhaps the understatement of the decade. Without her, My Cousin Vinny is just another mid-level, forgettable comedy. But infusing that unmistakable accent and raw comedic force into each scene and you have one of the most memorable movie going experiences in modern memory. And every bit deserving of the Best Supporting Actress Oscar all these years later. Mona Lisa Vito isn’t just a character — she’s a way of life.

– Mitch Roush

36. Max Fischer (Jason Schwartzman) | Rushmore (1998)

Still to date the best character that Jason Schwartzman has played, Max Fischer is a precocious, pretentious student who has an extremely high opinion of himself, but is unwittingly striving for meaning and purpose in his life. He attempts to fill the void by winning the affections of someone who he discovers is in a relationship with a character played by none other than Bill Murray, and all hell breaks loose. Schwartzman manages to make an unlovable character lovable as hell, bringing all the smugness that the part requires without losing any of the innate charm he has as a performer.

– D.N. Williams

35. Ace Ventura (Jim Carrey) | Ace Venture: Pet Detective (1994)

Okay, so in retrospect (and even at the time) the movie is a transphobic mess and the humor could at best be termed “adolescent” – but this was the first movie to let Jim Carrey go as crazy as he wanted. It turns out he could go pretty crazy, and though Ace is a crude and crass as they come (“I want to… ASS you a few questions”) he was also weirdly endearing (especially in the the animal sequences) and hilarious. It turned out that the rubber-faced guy from In Living Color had some charisma, and while he’d go on to do bigger, better and less mean-spirited things Ace was his first break-out character. Carrey wanted the homophobia/transphobia to be so broad and ridiculous that you couldn’t take it seriously – I don’t think he succeeds and in that, and other things, the movie can be hard-to-watch. Outside of those elements Carrey’s bargain-basement Dr. Doolittle is usually funny enough that you generally laugh in spite of yourself.

– Bob Cram

34. Jeffrey Goines (Brad Pitt) | 12 Monkeys (1995)

In 1995, Brady Pitt was named one of the 25 sexiest stars in film history by Empire magazine and the “Sexiest Man Alive” by People. That same year, he starred in Terry Gilliam’s 12 Monkeys as psychiatric patient-cum-environmental activist Jeffrey Goines.

If you’re familiar with Gilliam’s classic dystopian sci-fi, you know that Pitt’s turn as the loony Goines isn’t exactly congruent with his status as the 21st century male sex symbol. Pitt’s performance on its own is admirable, but it’s made that much more memorable and interesting because of that incongruity. It’s almost like the would-be star is thumbing his nose at the superficiality of his burgeoning stardom, mirroring the actions of the Goines character in rejecting the role of trust fund baby that he was born into.

It’s hard not to wonder, then, if Pitt, like Goines, wasn’t just slumming for a time, playing at method acting as Goines plays at activism, because the next time the heartthrob would challenge himself in an unflattering role (at least, that I can think of) would be in the Coen Brothers’ 2008 comedy Burn After Reading. And that’s really too bad for us film fans, because Pitt is capable of so much more than just looking pretty.

– Billy Dhalgren

33. Deputy U.S. Marshal Sam Gerard (Tommy Lee Jones) | The Fugitive (1993)

Andrew Davis’ The Fugitive is a movie with two protagonists – a man on the run from the law and the lawman tasked with hunting him down – and it’s a tribute to the actors and the director that we end up rooting for both men equally. Tommy Lee Jones was so good as Deputy U.S. Marshal Sam Gerard that he won on Oscar for the role. Gerard is smart, principled, dedicated and surrounded by a crew of professionals that treat him as friend, mentor and surrogate father figure. Even if he doesn’t want them using words around him that have no meaning.

His dedication and professionalism in the hands of another actor could have turned the character into a didactic opponent to Harrison Ford’s Kimble. Luckily we had Jones, who even made the line “I don’t care!” in response to Kimble’s “I didn’t kill my wife” into something to laugh at and even admire, rather than a knee-jerk, dead-end “my way or the highway” response of a procedure-bound bureaucrat. As satisfying as it is to see Kimble finally take down the man who killed his wife it’s almost as good to see Gerard finally come around. “I know it, Richard.”

As good as the character was, it really needed writers like Jeb Stuart and David Twohy and another great protagonist to work with/against. Sadly, U.S. Marshals didn’t benefit from either and as a result we didn’t get that Sam Gerard franchise we really deserved.

– Bob Cram

32. Blake (Alec Baldwin) | Glengarry Glen Ross (1992)

A performance so iconic, so career defining, you could be forgiven for thinking he was not only in the entire movie but was the main character. Written specially for the actor by Mamet, the role is unique to the film adaptation as there is no Blake in the original stage play. The most quotable part of the film, the thing most people remember about the movie wasn’t even in the play. That goes to show how good a writer Mamet is—that he can somehow improve upon an already successful story—but a true testament to the talents of Baldwin, in that Mamet not only knew he could do it but was good enough to be gifted such a bounty of rich dialogue. “Second prize, a set of steak knives. Third prize is, you’re fired.” The fact that Judi Dench won for Shakespeare in Love, a role that was of equal length but markedly inferior in quality and Baldwin wasn’t even nominated for this is a goddamn travesty. This is more than a cameo, it’s one of the greatest performances in cinema, that just happens to only last eight minutes.

– Sailor Monsoon

31. Albert Goldman (Nathan Lane) | The Birdcage (1996)

I could tell you that Nathan Lane is my all-time favorite performer. Or that his ability to capture impeccable character choices every single time out of the gate on both stage and screen is damn near unmatched. Or that he deserved an Oscar for his turn as Albert Goldman. I could say a lot of things. And to be honest, I think all of them would be true.

Albert is a stunning unicorn if there ever was one. A drag singer and performer at Florida’s favorite late night locale, The Birdcage. Partner to club owner, and a heart so big you can’t help but marvel at all the absurd and colorful warm fuzziness. But it’s in the insecurity and utter silliness of situational hijinks and fractured love that Lane’s Albert Goldman really shines.

This character, much like the film, just feels like a rare gift. Something we were given that almost has no right to provide us with that much entertainment and perfect actor-to-character pairing. Such fantastical hysterics that could only be pulled off by a performer that lives at the intersection of over the top and grand display. Indeed, Albert Goldman is a ’90s icon and the key driving force to what I believe to be the best comedy of the decade. And I say this with all seriousness and sincerity, but no one, and I mean no one, else could’ve played this role this well. That is no small feat. Watch a few of his best moments and tell me it’s not the greatest thing you’ve seen [or at least the most fabulous].

– Mitch Roush

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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!