The 100 Greatest ’90s Movies of All Time (60-51)

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, 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.

60. Good Will Hunting (1997)

This movie has it all – thick Boston accents, complicated math problems, quippy dialogue, baseball, therapeutic breakthroughs, and double burgers. Some might write Good Will Hunting off as being cheesy or too melodramatic, but that remains part of its charm. The script, penned by childhood friends Matt Damon and Ben Affleck, is filled with emotion and wit. The characters are all so wonderfully realized, and each is afforded at least a singular moment to shine. The way that camera hangs on Robin Williams’ face as he delivers the famous park bench monologue will always shake me to my core.

Raf Stitt

59. Malcolm X (1992)

Few directors have the bonafides to be able to make something as big and sweeping as Malcolm X. Luckily for us, Spike Lee is not like most directors. And because of that, we do have a film as bold and as beautiful as this one. Malcolm X remains one of the best biopics of all time due not only to Lee’s incredible direction but also because the always-great Denzel Washington delivers one of the best performances of his career. The 3-hour plus runtime might scare some folks away, but Malcolm X is more than worth it. An epic biopic that just about matches the larger-than-life stature of the man that it’s about.

Raf Stitt

58. The Insider (1999)

“Are you a businessman, or a newsman?” It’s tough to pick just one great scene in Michael Mann’s The Insider, but the moment when 60 Minutes producer Lowell Bergman (Al Pacino) finds out that CBS is canning the interview with tobacco company whistleblower Jeffrey Wigand (Russell Crowe) is a contender. Watching Pacino take all the execs to task, including Philip Baker Hall as 60 Minutes creator Don Hewitt, is as riveting as any action scene. And the moment when Mike Wallace (Christopher Plummer) sticks the knife in by revealing he’s siding with the suits is as devastating as any heroic loss. The Insider is just full of talking heads, closeups and pauses, and angry shouting. It should be boring as shit, but it’s filmmaking at its finest. As much a character study about two driven men – and you should see it again just to remember how freaking great Russell Crowe can be when he’s given the right material – it’s also about the downfall of television investigative reporting and how corporate America turned the legal system against… well, all of us.

Bob Cram

57. Waiting for Guffman (1996)

We don’t see a lot of mostly improvised mockumentary-style feature-length films. Probably because it’s an extremely hard feat to achieve. This is why the fact that Waiting for Guffman works at all is a minor miracle in itself. It’s a testament to the genius of director Chris Guest, his co-writer, Eugene Levy, and the whole cast of actors. Beyond being one of the funniest movies of the ’90s, Waiting for Guffman is a movie full of heart. Despite its heartbreakingly hilarious ending, it’s a fairly optimistic movie. One that loves its characters and its audience equally.

Raf Stitt

56. The Virgin Suicides (1999)

Based on the novel of the same name by author Jeffrey Eugenides, The Virgin Suicides tells the story of five sisters who, due to their overprotective family, become isolated and shut off from the outside world and because of this, become more and more despondent. After the youngest one, Celia (Hanna R. Hall), tries to kill herself, the rest of the sisters are put under house arrest. Due to their beauty, they become the object of desire of the local boys but since none of them can get close to them, they’re all shrouded in mystery. They almost become a suburban myth — the unattainable Lisbon Sisters, but within the house, their lives are anything but a fairy tale.

Watching these girls, Lux (Kirsten Dunst), Mary (A. J. Cook), Therese (Leslie Hayman), Bonnie (Chelse Swain), and Cecilia slowly have the life and happiness drain from their lives, is a tragedy on the level of Shakespeare. Sofia Coppola’s directorial debut is kind of like the anti-teen film. There’s no cliché meet cute or inspirational feel-good vibe, it’s a film whose title let’s you know going in what the tone will be and it ain’t no bait and switch. It’s an emotionally devastating portrait of teen angst and desperation made unforgettable by five amazing performances.

Sailor Monsoon

55. L.A. Confidential (1997)

Set in the 1950s. Three cops, Ed Exley (Guy Pearce), Bud White (Russell Crowe), and Jack Vincennes (Kevin Spacey), all with three different motives all get pulled into the same case; an unsolved murder in a coffee shop called “the night owl murder case”. Each one has their own type of moral code that they all live by. Ultimately they come to terms with how their honor levels relate to the way they see justice as well as how that relates to the justice system they have sworn to uphold. They will have to figure out how to do what’s right rather than what’s right for themselves.


54. The Iron Giant (1999)

In the thick of the Disney Renaissance, The Iron Giant wasn’t an immediate home run. But over the past 30 years, it has steadily gained traction as people realized it for what it is: one of the greatest animated films of all time. Disney movies had (and mostly still have) a formula of mostly being sort of musical fairy tales. Brad Bird boldly ignored those conventions and created a much more mature tale, while capturing the wonder of childhood. The film perfectly balances adventure, heart, and comedy while exploring mature themes such as death, purpose, and free will. The titular giant has gained a resurgence in pop culture such as Ready Player One and Ted Lasso in recent years as the film rose from a box office flop to a cartoon classic. 

Jacob Holmes

53. American Beauty (1999)

I don’t think any actor had a better year in 1999 than Mena Suvari… at least when it came to movies with the word “American” in its title. After breaking out as the innocent choir girl Heather in American Pie, Suvari went on to play the virgin Angela in American Beauty. Of course, Suvari isn’t the protagonist in either film, that honor would go to the men driving to have sex with her. For American Beauty, that’s Kevin Spacey’s Lester Burnham, a middle-aged man suffering a midlife crisis who jerks off in the shower because he’s unhappily married to his wife. Of course, nowadays it’s hard to not draw parallels between Spacey’s character wanting to have sex with his daughter’s teenage best friend and allegations of sexual misconduct against the actor that have emerged over the last few years. While I’m not the biggest fan of American Beauty, I respect how the film explores the perception of beauty and personal satisfaction within America. So often, we miss the real beauty around us because we’re busy trying to obtain something that someone else told us was beautiful. Like the damn plastic bag in this film, beauty can be found in anything — it’s all about perspective.

Marmaduke Karlston

52. Boys Don’t Cry (1999)

Based on the true story of Brandon Teena (Hilary Swank), a transgendered man who fell victim to a hate crime and was murdered by two men in Nebraska in 1993. It follows Brandon as he falls in love and has a relationship with a girl named Lana Tisdel (Chloë Sevigny). Things go awry when the people who Brandon is staying with discover that he is genetically a girl. Disapproving the relationship between Brandon and Lana, and the life that he lives with two of Lana’s friends, Brandon is fatally shot in the head.


51. Close-Up (1990) 

I never include documentaries in my top 100 lists because it’s near impossible to compare and rank reality against fiction but Close Up is a movie worth breaking the rules for. A unique hybrid that uses a sensational real-life event—the arrest of a young man who impersonated the well-known filmmaker—as the basis for a stunning, multilayered investigation into movies, identity, artistic creation, and existence, in which the real people from the case play themselves. It blurs the line between what is real and what isn’t. Is a reenactment less real because it’s staged even though it’s emotionally true to what happened? The film raises interesting questions about reality and storytelling and offers insight into the mind of a man so desperate for fame, he’d create a web of lies and abandon all logic to keep his grift together. It’s not exactly a documentary nor is it a dramatization, it’s something in the middle that is more wild than the truth and more entertaining than a recreation. It lives apart from everything else. An Island of one unlike anything you’ve ever seen with a story you’ll never forget.

Sailor Monsoon

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