The 100 Greatest ’90s Movies of All Time (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 successful. Everything seemed copacetic, which lead to everyone doing their own thing. Studios weren’t competing nor copying but instead, had a healthy rivalry. Animation was back in a big way and was evolving in terms of technology and maturing in terms of storytelling. 

It was a fertile period for cinephiles and with that came a wellspring of iconic movies that we took for granted. We didn’t appreciate how many new masters it was producing, the big swings the old masters were taking or how quickly it was taking cinema in terms of innovation. And since we’re all still drunk in love with the goddamn 80s still, this decade doesn’t seem to be getting any love any time soon. This list is a reminder of how many bangers this decade produced and why it deserves more respect.

These are the 100 Greatest ’90s Movies of All Time.

100. 10 Things I Hate About You (1999)

At first glance, the plot of 10 Things I Hate About You is an overly complicated version of “nerd likes the popular girl.” Cameron (Joseph Gordon-Levitt) is the new kid at a Padua High. He has a crush on Bianca Stratford (Larisa Oleynik), a beautiful but seemingly dim-witted popular girl. Bianca’s father, hilariously paranoid obstetrician (Larry Miller), makes a rule that she can’t date until her older sister Kat does. Kat (Julia Stiles) is immediately established as ill-tempered and antisocial — nearly feral, in fact.

And that’s just the beginning. The plot gets even more ridiculous, with Cameron and his straight-man sidekick (David Krumholtz) tricking high school hunk/absolute dirtbag Joey Donner (Andrew Keegan) into paying someone to woo Kat into dating. Donner, of course, does so with the intention of sleeping with Bianca. In comes the last member of the scheme, Patrick Verona (Heath Ledger in his breakout role), the bad boy who gets paid to date Kat and, of course, ends up falling for her.

10 Things is a clever adaptation of Shakespeare’s Taming of the Shrew (which somehow has an even more convoluted and maddening story). While the surface level plot is a tale of boys juggling absurd schemes to get the girls, the heart of the plot is found in the depth of love Kat has for her younger sister and the evolution they both undergo in understanding themselves and each other.

As someone who has three daughters, I find Stiles and Oleynik perfectly capture the relationsip between sisters, with the love and the annoyance flowing freely. Their performances are authentic, hilarious and heartwarming. Ledger, of course, is endlessly charming; Gordon-Levitt is adorable, albeit completely and constantly misguided in his efforts. Keegan is perfect as an absolute prick. And in perhaps my favorite bits of insanity sprinkled throughout the film, Allison Janney just slays as the disinterested school counselor who spends most of her workdays writing romance novels.

R.J. Mathews

99. The Celebration (1998)

Family dinners can be awkward affairs. No one likes meeting up with relatives who you haven’t seen in months, or even years, and trying to pass off small talk and show interest in each other’s lives. In terms of uncomfortable get togethers, The Celebration takes things to a new level. It tells the story of a family who gathers to celebrate their father’s 60th birthday. For the first portion of the movie, things seem fine. Maybe a little tense, but eventually you begin to feel there is a foreboding sense of dread lingering in the background. As the birthdays speeches and thank yous progress, a bombshell is dropped and some incredibly dark and disturbing family secrets are exposed. The performances from all the leading cast are quite exceptional and really help hammer home the emotional distress being experienced. A classic from director Thomas Vinterburg that paved the way for The Hunt and Another Round many years later.

Lee McCutcheon

98. Run Lola Run (1998)

Gimmicks in movies aren’t unusual. In fact, I can think of several movies from the 90s off the top of my head that used gimmicks effectively. Fight Club tricks the audience into thinking Tyler Durden and Edward Norton’s unnamed character are entirely different people only to find out at the end that the Narrator and Durden are the same person. The Matrix had Bullet Time. Pulp Fiction tells its story out of order. Scream cleverly revitalized the slasher genre by making decades old horror tropes part of the film’s meta commentary.

Not all gimmicks stand the test of time, though. The Blair Witch Project’s found footage worked at a time when not every detail of a film’s production was widely known. Once the cat was out of the bag, though, The Blair Witch Project loses much of its luster, and most of its rewatchability. Baz Lurhman’s Romeo + Juliet…to be honest, I hated that movie from the first time I saw it in theaters. But if it’s gimmicky approach to Shakespeare ever had any appeal, that time has long since passed.

Run Lola Run employs a few different gimmicks, and, in contrast to The Blair Witch Project and Romeo + Juliet, its gimmicks somehow manage to enhance and encourage repeat viewings.

Although not a traditional time travel movie, Run Lola Run’s repeating time loop plot structure works much the same way that other more obvious time travel movies work with Lola using knowledge gained in previous time loops to effect changes on subsequent loops. The structure is very gimmicky, but like Pulp Fiction, Run Lola Run never feels stale or tedious.

This will probably get me flamed in the comments, but I find that most films that mix traditional animation with live action just never age well for me, but the animated sequences in Run Lola Run only add to the charm of the movie—even 25 years after its original release.

A big part of Run Lola Run’s commentary revolves around chaos theory’s butterfly effect. The effect of Lola’s actions and decisions (even tiny ones) on the lives of the people she encounters are very effectively shown through different series of still images cleverly edited in. The images flash by quickly and somehow never manage to slow down the narrative, but because the plot moves so quickly, the effect is not unlike riding in a car and seeing something interesting along the roadside but not being able to slow down and get a really good look at what you just saw. Run Lola Run moves on before you can really consider what you just saw. Multiple viewings are rewarded, because your understanding of the movie and your perspective shifts as you digest the various bits of information that are thrown at you as Lola dashes from scene to scene.

Billy Dhalgren

97. One False Move (1992)

After they become wanted by the law after a series of brutal drug hits and police slayings, a trio of criminals traveling from Los Angeles to Houston, decide to hide out in Arkansas until the heat dies down. Two detectives from the LAPD, who are already on the case, contact the town’s sheriff, to alert him of the fugitives’ presence in the area. Eager to help and ready for action, the sheriff teams up with the detectives on, what will eventually become, a mission of carnage that will leave many casualties in its wake. Constantly unfolding like a great mystery yarn and expertly ratcheting up the tension like a suspenseful drama, One False Move is neo noir at its finest. The acting is exceptional, the direction is on point and the script is like a Russian nesting doll of awesome, with each doll offering up a smaller but equally as important piece of gold. This should’ve done for Carl Franklin what Fargo did for the Coen Brothers. It’s every bit its equal in terms of quality and if I’m being honest, although Fargo is a better constructed movie, the twists and turns of One False Move make it a superior movie in my opinion.

Sailor Monsoon

96. Misery (1990)

I think there are certain movie scenes that stand out in the collective memory of the universe. Even if you’ve never seen Misery, the odds are good that you somehow recall the shock and horror of watching Annie Wilkes (Kathy Bates) standing over bed-bound Paul Sheldon (James Caan), breaking his ankles with a sledgehammer. Perhaps I’ve gotten ahead of myself though.

Based on Stephen King’s 1987 novel of the same name, Misery tells the story of Sheldon, a novelist who found fame with a series of romance novels focused on the main character Misery Chastain. Sheldon has decided to take his writing career in a new direction, then promptly gets caught driving in a blizzard, with his new manuscript riding shotgun, and careens off the side of the road. He wakes up with two broken legs and a dislocated shoulder in the isolated home of his self-proclaimed No. 1 fan. Wilkes holds him captive and forces him to write a new ending for Misery (his novel character, that is).

Misery is one of my favorite adaptations of a King novel. Bates chills the soul with her masterful portrayal of Wilkes’ oscillation between childlike and psychotic (a role for which she won a well-deserved Academy Award). Caan spends most of the movie bedridden, a passive player in Wilkes’ demented game. It’s an interesting take for an actor otherwise known for his tough-guy roles, but he makes an incredibly sympathetic victim whom the viewer is eager to cheer for when he finally gets his moment to shine.

R.J. Mathews

95. Man Bites Dog (1992)

For some horror directors, simply scaring an audience isn’t enough. Some want to shock the viewer, by any means necessary. Whether that’s depicting extreme subject matter such as infanticide or rape, including unsimulated sex scene, real-life animal deaths or just pushing violence as far as it can go. Most attempts go so far past socially acceptable, that they lose their impact. It stops meaning anything when all you’re seeing is nonstop scenes of corn syrup, red dye, and women crying. Most of it is unwatchable misery porn from edge lords but there are some films that succeed in truly shocking audiences. Films like Maniac and Henry: Portrait of a Serial killer have never not been effective at upsetting people nor has films like Cannibal Holocaust or Salò, or the 120 Days of Sodom lost their ability to offend and disgust. Between those two behemoths of controversy, lies Man Bites Dog.

The activities of rampaging, indiscriminate serial killer Ben (Benoit Poelvoorde, in an all-time great performance) are recorded by a willingly complicit documentary team. Eventually, the line between what is right and wrong and what is fiction and non-fiction starts to blur once the camera crew itself starts to actively participate in the crimes. A pitch-black satirical comedy, Man Bites Dog is one of those films that’s not afraid to go all the way. The film opts out of the extreme blood and guts violence (don’t worry, there’s still a ton of violence in the film) in favor of a more chilling, and subtle approach to shock cinema. Instead of carving people up, Ben yells at an old lady long enough to give her a heart attack. Or regales the camera crew in stories of proper dead baby disposal. He crosses every line and obliterates every taboo. He does whatever he wants but since he’s so charismatic, we’re complicit by not looking away. Our enjoyment makes us accomplices, which is the point. A shocking movie that out shocks the other shock movies that also have a point? Now that’s truly shocking.

Sailor Monsoon

94. La Haine (1995)

When I was asked to nominate movies for this list, I asked myself again and again what are some common traits that make a movie truly great. And one of the things that I came back to again and again is rewatchability. Most of the movies that I consider great are movies that I find myself returning to again and again.

La Haine is one of those movies.

Despite the heavy subject matter, the movie moves like a light thriller. It never gets bogged down under the weight of the heavy questions it’s asking the audience to consider, and it’s not so heavy handed that you feel like you’ve gotten everything the movie has to offer from a single viewing. It’s tautly paced, expertly directed and acted, and it will leave you thinking long after the credits have rolled.

Billy Dhalgren

93. Three Kings (1999)

“Hit him with the blinding power of American sunshine.” David O. Russell’s Three Kings is a pro-war movie, an anti-war movie, a drama, a comedy, a satire, an action flick a… well, it’s lots of things, is what I’m saying. I wasn’t expecting much from a movie starring Ice Cube, Mark Wahlburg and that guy from ER. And Spike Jonze. (My exact thought by the time I saw it: “the guy who directed Being John Malkovitch?”) I enjoyed the hell out of it, though – the combination of dark humor (a treasure map up a dead guy’s ass?), action, gross-out (see aforementioned dead guy’s ass), music and character chemistry hit all the right buttons for me, even if some of those elements were juxtaposed in weird ways. The cinematography also stood out – shot on Ektachrome, it provided an enhanced contrast and subtle color palette that somehow made everything seem more intense. I remember thinking that parts of the way Pitch Black was shot had to be inspired by the look of Three Kings. Those “inside the body” effects were amazing as well, though we’d end up with a surfeit of them from CSI starting the following year.

Made in 1999 about the first Gulf War in 1991, Three Kings remains a relevant watch even today. You’d have thought we’d have learned something. That this would be more of an artifact of its time, but no. I was just thinking this past fall how this movie could have been made last year, set in the pullout from Afghanistan. Or set in Ukraine. Definitely worth a watch. Or another watch.

Bob Cram

92. Wayne’s World (1992)

While not the best adaptation of a Saturday Night Live property (no MacGruber, it’s still The Blues Brothers), Wayne’s World IS the most successful. It hit the cultural zeitgeist just right, blowing up at the box office, spawning a decade’s worth of catch-phrases (“…not!” and “That’s what she said.” being two I would happily never hear again), making “Bohemian Rhapsody” somehow even bigger than it already was, and turning Michael Myers into a movie star. Directed by Penelope Spheeris (Suburbia, The Decline of Western Civilization 1 & 2), Wayne’s World takes the thin premise of a couple of metal-head goofballs with a cable access show and spins out a glorious slapstick comedy, with a minor dramatic thread of “success corrupts.” Yeah, it kinda falls down a bit at the end – I still remember spitting out my soda at the “Old Man Withers” ending – but it’s still a fun romp, with a ton of great music and cameos. I’m sure there are better Michael Myers movies (don’t say Halloween), but this will always be my favorite.

Bob Cram

91. Fear and Loathing in Las Vegas (1998)

“What? No. We can’t stop here. This is bat country.” Man, this movie is a wild one. I really didn’t know what to expect the first time I saw it. I hadn’t read any Hunter S. Thompson yet. And after I saw it I had to try and sort it all out. It was just so trippy and and all over the place. I loved it. As much as everyone raves about Depp’s Dread Pirate Keith Richards impersonation, I think he outshines that character here with his balls to the wall Hunter S. Thompson impersonation. Plus, Benicio is just outstanding as his attorney Raoul Duke. Keep your eyes peeled for a ton of weird little things in the background and some familiar faces you might only see for a few seconds to minutes too.

K. Alvarez


What are some of your favorite ’90s movies? Maybe they’ll show up later in the list!