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.