How could I possibly put together a list like this and leave off Seven? Or Wayne’s World? Or The Fifth Element? Or The Sixth Sense? Or any of the hundred other ’90s movies people love so much? There are a few possible answers to those very natural objections. The most obvious is that what classifies the “best” of any category is a matter of taste. But truthfully, if this included every great ’90s movie it would be an unwieldy mess.
On demand: Amazon Video, YouTube, Apple TV
Jurassic Park is what happens when a studio trusts intelligent people to make a good movie. These are fully formed characters, put in a dangerous situation, dealing with complex philosophical situations. Everyone has a full arc, with deep meaningful change brought about after massive confrontation with an existential threat. There aren’t any loose ends in the script that I can see and no one’s a caricature. It’s family friendly while avoiding saccharine condescension, which seems to generally be achieved by trusting that your audience, kids and adults, is smart enough to understand what’s going on. And also there’s dinosaurs, which is pretty cool.
Good Will Hunting
Stream: Amazon Prime Video
I try to watch Good Will Hunting once a year, if only to refresh my memory of the Sean Maguire/Will Hunting relationship. There are a hell of a lot of layers to their relationship and repeated viewings peels them back. You see more of the reasons behind Will’s behavior, how Sean slowly wins Will’s trust, how hard he works to keep it, and how comfortable and open Will becomes in Sean’s presence. It’s one of the few movies that really understands modern masculinity and all the baggage that goes with it.
Stream: Amazon Prime Video, YouTube, Roku
I pride myself on having retained my baseball fundamentals. I jump at any opportunity to watch a live game, and James Earl Jones narrates any baseball histories I read. A lot of this is because The Sandlot plays on repeat inside my head. There’s a good chance that, if I’ve spaced out, I’m rewatching the sandlot kids’ game against the little leaguers. What sticks with me about The Sandlot is that it’s made by people who truly understand their subject matter. Not just baseball, but the way kids think and talk to each other, the difficulty of being the new kid, the desperation you feel making new friends, and the importance of getting into trouble and pulling yourself back out again.
Terminator 2: Judgment Day
On demand: Amazon Prime Video, YouTube, Apple TV
Terminator 2: Judgement Day is everything you hope a sequel will be. It raises the original’s stakes, steps up the action, tightens the writing, and fleshes out new characters and develops existing characters. Even more importantly, it actually has something to say. At no point in Terminator 2 do you ask, why the hell does this exist? And, if you do, there’s a real answer beyond box office figures. The first movie didn’t fully resolve the struggle between Skynet and humanity and really only told Sarah Connor’s story. It makes sense to follow that up with an exploration of one of the bigger moments in John Connor’s life: the first time he encountered undeniable proof that his mom was telling the truth.
Saving Private Ryan
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It would be an understatement to say Saving Private Ryan defines the WWII genre. It’s so well made that virtually every other World War Two project, sans the other Spielberg/Hanks collaborations, pales in comparison. There are historical inaccuracies you can whine about if you want–the big dramatic fight at the end of the movie is entirely fictional, in real life the army sent a single chaplain–but to do so misses the point of the movie entirely. Saving Private Ryan depicts the chaos and desperation of war so accurately, that Dick Winters (the real one, not Damien Lewis in Band of Brothers) used it as a resource to show his friends and family why he spoke so sparingly about the war.
Stream: Amazon Prime Video
It’s unlikely that there’s a Cool Material reader who hasn’t seen Pulp Fiction. This is Tarantino at his best, with iconic moments, lines, and characters absolutely spilling out of the movie. John Travolta, Samuel L. Jackson, Bruce Willis, Uma Thurman, and Ving Rames all turn in career defining performances over a soundtrack that begs to be played on repeat in a vintage car.
The Silence of the Lambs
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Jodie Foster remarkably holds her own next to Anthony Hopkins. She plays the FBI trainee, Clarice Starling, with as much nuance and depth as Hopkins does Hannibal Lecter, a special achievement given that a good bit of Foster’s role is reacting to one of the most unsettling characters to ever be in a movie. Just like Foster’s performance, the core strength of Silence of the Lambs is in its subtlety. Very little of the movie plays on the surface, with most of the characterization and plot happening through insinuation. It’s so confident in its subtleties that Starling’s realization who Buffalo Bill is isn’t explicitly stated. It all plays through small changes in expressions and body positioning until it explodes in her pursuit of the killer.
Fargo is the superior Coen brothers movie. It’s a showcase of their greatest talents. Sharp, witty dialogue, life or death stakes, and an almost pathological devotion to mundane detail. It’s that detail that makes their movies, almost all of which follow outlandish or exaggerated situations, feel so true to life. What pushes Fargo over the edge is Marge. She’s the combination of a few different lesser seen movie characters (honest cop, pregnant, competent and intelligent but not evil), and it’s thoroughly satisfying to watch her work.
Stream: Amazon Prime Video, HBO Max
In anyone else’s hands, Goodfellas would be a circuitous, disjointed, self-indulgent mess, but with Martin Scorsese in the chair, it’s a classic. That’s partly because Scorsese is one of the few directors who could actually keep the whole thing straight. Goodfellas, like the actual mafia, has bombastic personalities bouncing off each other and competing for screen time. Scorsese’s tight grasp on realistic dialogue, his willingness to let his actors improvise, and a more organic approach to storytelling mean he’s apt to keep Goodfellas coherent, even as the characters become less and less so.
Stream: HBO Max, Amazon Prime Video
It’s a constant wonder to me that Office Space didn’t prompt an immediate revolt in the white collar sector. Everyone I’ve ever talked to, whether or not they’ve worked in an office, knows exactly what Office Space is making fun of and they hate it with every fiber of their being. Any laughter you hear during the movie is a cathartic release from the soul. It’s a lessening, however slight, of the pressure building up from the massive, prolonged existential crisis of the American service economy. Everyone who hates their job with the kind of passion generally reserved for Bond villains is looking for ways to make it hurt a little less.
Men in Black
Stream: Amazon Prime Video
It’s easy to forgot how good the original Men in Black is. It was a family favorite, so I always assumed my memory of its quality was heavily colored by nostalgia. Imagine my relief when I rewatched it and didn’t cringe at what my younger self thought was entertaining. Something else I picked up on now that I’m older was just how genuinely funny Agent K is. Will Smith is obviously great as a fast talking, cocky, charismatic recruit. With Tommy Lee Jones, they could have easily turned him into a close-to-retirement curmudgeon, which, to be fair, is occasionally hinted at. Instead, he’s a patient but deathly sarcastic mentor guiding his new trainee, and the audience by extension, through a highly complex world he’s inhabited for a long time.
Stream: Amazon Prime Video, Paramount+, Roku
Clueless is Mean Girls for the ’90s. Or Mean Girls is Clueless for the 2000s. Either way, if you like one, you’ll like the other. The main thing Clueless does that lot of other movies in the genre don’t is treat its characters with respect. Most teen comedies treat high school girls like vapid, irredeemable ditzes, vindictive shrews, or somehow both. Clueless recognizes that being a bit airheaded doesn’t mean you’re worthless, you’re just a little late in gaining awareness outside yourself. It’s a realization we’ve all had to have, this is just what it looks like when it happens to a rich valley girl. It’s also the movie that brought Paul Rudd into the mainstream, which may or may not win you some bar trivia at some point.
The Big Lebowski
Stream: Amazon Prime Video
Coasters. Art prints. Rugs. Cottages. The iconic White Russian. There are so many things from the Coen Brothers The Big Lebowski that it’s hard to pinpoint even one Dude-ism that stands out most. Between the cast, the direction and the story, it’s no wonder that this supremely watchable film has spawned conventions, bowling tournaments and assumed a cult-like status over the years.
Stream: Amazon Prime Video, Peacock TV
Schindler’s List is the definitive Holocaust movie and isn’t so much entertainment as it is something that needed to be made. If you’re going to sit down for it, make sure you’ve blocked out at least five hours, because a serious bout of depression and self-examination comes with every viewing. There’s no question that Schindler’s List is one of the most impactful films ever created, which is probably why it ranks in the Top 10 in both the AFI and IMDB lists of greatest films of all time. No list of ’90s films would be complete without this harrowing tale.
Stream: Amazon Prime Video, Pluto TV
The hardest part about picking the best films from the ’90s might actually have been selecting which Tarantino flicks to include. Reservoir Dogs is a great heist movie and Jackie Brown is severely underappreciated, but Pulp Fiction might be the auteur’s greatest work ever. It’s smart. It’s funny. It’s violent. It tells a completely ridiculous story that’s enthralling and bewildering while still keeping you invested from beginning to end. From being ultimately quotable and spawning a cottage industry of BMF wallets to the fact that it’s held up after all these years and won numerous awards, Pulp Fictions is one of the best films ever.
Stream: Amazon Prime Video, Netflix
“Run, Forrest, run!” “Momma always said life is like a box of chocolates.” Anything about Lieutenant Dan. The movie that won six Oscars and killed many more boxes of Kleenex is one of the most quoted films of all time and remains one of the greatest performances esteemed actors Tom Hanks and Gary Sinise ever turned in. Describing Forrest Gump as an emotional gauntlet doesn’t do this iconic work justice, but it’s the closest you can get in two words.
Stream: HBO Max
Bullet time. Alternate realities. Humans as batteries. There are a lot of things that The Matrix dealt with that would ultimately be imitated, appropriated or outright stolen in other films, but the original action/sci-fi tale will always tell the story the best. The Wachowskis created a dystopian future filled with questions, violence, special effects and more questions that leaves people debating almost twenty years later. They might not have delivered with the sequels, but the original is good enough to forgive that.
Stream: Hulu+, Paramount+
Written by Palahniuk and directed by Fincher, Fight Club is a film that, despite being based on fantastic source material might be a better movie than a book (though Palahniuk already kind of thought that). Pitt and Norton give fantastic performances in a movie with one of the most epic twists of all time. The movie somehow manages to deal with everything from dead end jobs and soap making to personal awakenings and physical violence in a way that still endears you to the characters and the ideals they stand for.
Available on demand: Amazon Prime Video
Described by critics as a tale of “American suburban angst” and “quietly confrontational, genuinely haunting and unexpectedly moving,” Happiness is a dramatic comedy starring Jane Adams, Jon Lovitz, Philip Seymour Hoffman, Dylan Baker, Lara Flynn Boyle and plenty of others that helped it turn out to be one of most unexpectedly great films of the decade. Directed by Todd Solondz, Happiness is a controversial and provocative film that deals with everything from divorce and a missing penis to controversial interpersonal relationships and love. It’s an indie film that’s absolutely worth seeing.
Available on demand: Amazon Prime Video, YouTube
Along with Tarantino, Wes Anderson is one of those iconic directors that’s hard to pick a favorite work for—even if he pretty much single-handedly made Bill Murray the cultural icon he is today. Anderson’s directorial style in Rushmore, combined with Owen Wilson’s writing and the acting of Schwartman, Murray, Cox, and the other Wilson brothers leads to the creation of a dark yet comedic film. Most people come to it through one of the ensemble cast’s work, so it’s a little more hidden than their other movies, but most people love Rushmore even more than whatever led them to it in the first place.
The Blair Witch Project
In what is mathematically one of the most successful independent film projects of all time, three students vanish while filming a documentary about the Blair Witch legend leaving only their footage behind. The terrifying film is shot in a found footage way that has since come to be known as the “Blair Witch style” and led to multiple imitations, artistic appropriations and complete rip-off films that are nowhere near as haunting as the original.
Being John Malkovich
Being John Malkovich is probably one of the weirdest movies ever created. John Cusack takes a new job only to find a tiny door that takes you into the head of John Malkovich before being spit out onto the New Jersey turnpike fifteen minutes later. It’s absurd. It’s complete madness. It’s so crazy that Malkovich himself wanted the film to be called Being Tom Cruise before it was released.
Originally released in 1995 by an otherwise unknown brand that would go on to become an international animation and film powerhouse, Toy Story was the first feature length computer animation ever released. Tom Hanks, Tim Allen, Don Rickles and the rest of an all-star cast deliver award-winning vocal capture performances animated by the skilled folks at Pixar in a film that would prove computer animation wasn’t just some kind of window dressing you could put in a live action movie. It could carry a film all by itself.
Additional writing by Ben Dahl