Looking back, the 1990s feels like a time of unbridled prosperity — especially when it comes to film. You couldn’t watch a movie without physically going to a theater or renting it from a video store. Money was necessarily exchanged for the movie to be viewed… which means that the ’90s were a straight-up cash cow for production companies.
Budgets were big, and bidding wars on scripts were even bigger. Studios felt comfortable taking creative risks, throwing money at plots many production companies would shy away from today. The result of this decade of dizzying confidence is a slew of enduring classics, of fresh and unique ideas put to screen.
1. Good Will Hunting
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Matt Damon and Ben Affleck have been such mainstay figures in Hollywood for decades now that it’s easy to forget how mythical and meteoric their entry into filmmaking was. But these two young, relatively unknown bros showed up in Hollywood with the script for Good Will Hunting and walked out with an Oscar and a lifetime on the A-list.
When an MIT professor (Stellan Skarsgård) puts a near-impossible math problem on his blackboard, he’s shocked to find that someone in the school has solved it… And that someone is the janitor, Will (Matt Damon). The professor helps Will, currently on parole, get permission from the court to study mathematics — provided he also receives therapy for his behavioral issues.
Good Will Hunting is a captivating and heartfelt drama that has been parodied, copied, and referenced, but never repeated. Ben Affleck is perfect as Will’s rough best friend, and Robin Williams won an Academy Award for his performance as the empathetic, unconventional, and no-bullshit counselor who just might be the one to help Will break out of his pattern of self-destruction and make something of his life.
How to watch: Good Will Hunting is now streaming on Max.
2. The Player
Biting, irreverent, and whip-smart, The Player is a perfect example of what Hollywood does best: make movies about itself! Griffin Mill (Tim Robbins) is a film greenlighter with a cushy life who starts to receive threatening postcards, presumably from a writer whose work he rejected. His anxiety about the messages leads him to a late-night confrontation with an aggrieved screenwriter that could ultimately unravel his entire world.
Directed by Robert Altman, The Player is a good-natured, self-aware satire that features a whopping 65 celebrity cameos and a highly choreographed, jaw-dropping, 7-minute, uncut opening sequence. An entertaining and thrilling watch for everyone, not just those “in the biz.”
How to watch: The Player is now streaming on Max.
3. White Men Can’t Jump
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Woody Harrelson is Billy Hoyle, a former college basketball player who hustles neighborhood courts in LA. His edge? The predominantly Black players assume Billy can’t play because he’s goofy and white. But when he beats Sidney (Wesley Snipes) at a one-on-one shootout, Sidney approaches him with a plan to hustle together and start making some real money. White Men Can’t Jump is energetic, clever, and fun, a fresh take on the sports comedy. Written and directed by Ron Shelton, it’s still a hit decades later thanks to a smart script and the radiant charisma of Harrelson, Snipes, and Rosie Perez, as Billy’s girlfriend.
How to watch: White Men Can’t Jump is now streaming on Max.
4. The Silence of the Lambs
Yes, it’s The Silence of the Lambs — the first horror movie ever to win the Academy Award for Best Picture.
Don’t get us wrong: Director Jonathan Demme’s chilling tale of a rookie FBI agent hunting for a killer with the help of [checks notes] another killer is unmistakably deserving of the groundbreaking accolade. But 30 years later, its legacy is a thought-provoking chance to chew over what Hollywood awards bodies do and don’t deem worthy of major recognition, particularly in the horror space.
Bask in the ghastly glory of Anthony Hopkins’ Hannibal Lecter and the steadfast stoicism of Jodie Foster’s Clarice Starling. Then consider queueing up another of the only seven horror films nominated for the most sought-after Oscar: The Exorcist (1973), Jaws (1975), The Sixth Sense (1999), Black Swan (2010), Get Out (2017), and The Shape of Water (2017), that last of which finally scored that second win — and yes, counts as horror if you’re going Black Lagoon rules.* — Alison Foreman, Entertainment Reporter
How to watch: The Silence of the Lambs is now streaming on Max.
5. And the Band Played On
In 1987, Randy Shilts published And the Band Played On: Politics, People, and the AIDS Epidemic, a groundbreaking and exhaustively researched investigation into the devastation of the AIDs crisis and the U.S. politics that slowed government intervention. In 1993, HBO adapted Shilts’ monumental work into a sweeping, emotional drama that stunned audiences with its honesty. Following American epidemiologist Don Francis (Matthew Modine) from Africa to San Francisco and beyond as he investigates a new mysterious illness, And the Band Played On is a beautiful tribute to those lost, an emotional and compelling mystery, and an excellent primer on the crisis for those looking to learn more.
How to watch: And the Band Played On is now streaming on Max.
6. Get Shorty
Chili Palmer (a smooth John Travolta) is a cool and competent loan shark in Miami who loves old films. So when he finds himself in Hollywood while tracking down a debtor on the run, he takes the opportunity to try his hand in the movie business. Turns out, the same skills that make him a successful mobster are exactly what just might make him thrive as a film producer.
Written by Scott Frank (Logan; The Queen’s Gambit) and directed by Barry Sonnenfeld (Men in Black), Get Shorty is both a cheerful send-up of mafia flicks and witty satire of Hollywood showbiz. Gene Hackman, Rene Russo, Danny DeVito, Dennis Farina, Delroy Lindo, and James Gandolfini are all spectacular, lending an incredible amount of charm to an already slick film.
How to watch: Get Shorty is now streaming on Max.
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Is the 1995 cult classic Hackers a thriller? A satire? A teen crime dramedy? Honestly, we may never know. But we do know this ridiculous story about a group of cyber-hacking New York teens in the early days of the internet takes itself dead seriously, which is part of why it’s so dang wonderful. There’s suspense, there’s romance, and there are absurd three-dimensional visualizations of cyber-security. What more could you possibly want?!
When teenage Dade Murphy (Jonny Lee Miller) and his mom move to New York, he starts hanging around some fellow floppy drive lovers (after proving his worth with the “four most commonly used passwords: love, secret, sex, and god.” It was 1995, folks!). But his new friends don’t know that Dade is secretly “Zero Cool” — the infamous hacker who crashed the NYSE at age 11 and was banned from using technology until his 18th birthday. And when another member of their crew accidentally comes across some dangerous information, these rollerblading tech teens (including a young Angelina Jolie!) will have to use all of their hacking skills to bring down the man.*
How to watch: Hackers is now streaming on Max.
8. The Hunt for Red October
Based on the best-selling Tom Clancy novel of the same name, The Hunt for Red October has the honor of being the very first in a long line of Jack Ryan movies and shows — and it’s also one of the best. Here, Alec Baldwin takes the stage as the impossible competent CIA analyst. When a Soviet commander (Sean Connery) takes his submarine rogue in the Atlantic Ocean, Ryan must figure out whether the crew of the Red October is planning a nuclear attack or hoping to defect. Directed by John McTiernan (Predator; Die Hard), The Hunt for Red October is a nail-biting thriller straight through to the stunning finish.
How to watch: The Hunt for Red October is now streaming on Max.
There aren’t many films out there popular enough to inspire a very popular-in-its-own-right TV show, but Fargo — with its snowy North Dakota setting and offbeat, black comedy style — has managed it with aplomb. One of the most memorable roles in Hollywood history, heavily pregnant police chief Marge Gunderson (Frances McDormand) attempts to untangle a messy murder and its links to some hired kidnappers, with things quickly spiraling in the amusingly chaotic way only Coen brothers’ movies can. Complimentary characters include a spineless William H. Macy as desperate-for-money car dealer Jerry Lundegaard, a chillingly dead-eyed Peter Stormare as hired kidnapper Gaear Grimsrud, and Steve Buscemi as his slimy partner in crime.* — Sam Haysom, Entertainment Reporter
How to watch: Fargo is now streaming on Max.
10. Princess Mononoke
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When you think of Hayao Miyazaki and Studio Ghibli, you probably think of Spirited Away or My Neighbor Totoro. But Miyazaki has been telling visually stunning stories for decades (including his latest, 2023’s The Boy and the Heron), and since almost all of his works are now streaming on Max, it’s time to dive a little deeper into the Ghibli catalog. Start with Princess Mononoke, the story of a leader determined to protect her lands from human consumption. Though she may align ideologically with Pocahontas, Princess Mononoke is far more ruthless, stopping at nothing to defend her fantastical home. Caught in the middle of this fight is a young prince, Ashitaka, hoping to help both sides achieve peace before a demon’s curse kills him.*
How to watch: Princess Mononoke is now streaming on Max.
11. Office Space
Ron Livingston is Peter, a miserable office worker who hates his job, his girlfriend, and his life. He agrees to go to a hypnotherapy session, but right after the hypnotist tells Peter to forget all his worries and cares, the hypnotist dies, leaving Peter in a breezy state of “no worries, bro.” He leaves his girlfriend and breaks all the rules at work — and is richly rewarded for his confident new maverick style.
Written and directed by Mike Judge (Beavis and Butthead; King of the Hill; Silicon Valley), Office Space is an iconic black comedy that embodies the embittered voice of the cubicle generation. Its cult impact was so great that Swingline created a new red stapler in honor of Stephen Root’s shy, repressed office worker, who spends the entire movie mumbling about his own.
How to watch: Office Space is now streaming on Max.
12. Shakespeare in Love
Joseph Fiennes is William Shakespeare in 1593 London, suffering writer’s block and trying to get his unfinished new play, Romeo and Ethel, the Pirate’s Daughter, off the ground. At auditions, he is inspired by a talented young actor’s performance, not knowing that the actor is secretly a woman, Viola, in disguise. (Women were not allowed to perform at the time.) Shakespeare tries to track down this mysterious actor but at the same time, he falls head over heels in love with an aristocratic and passionate woman he meets at a ball. She happens to be, you guessed it, Viola, from the audition.
Shakespeare in Love is a film with many layers. The characters are unknowingly doing a Twelfth Night while living out a Romeo and Juliet (Shakespeare climbs up Viola’s balcony to speak with her), the play they’ll all eventually perform live at the Globe Theater. Sweeping, poignant, and not interested in historical fact one little bit, Shakespeare in Love is a fantastic, indulgent romance with sumptuous costumes and ornate sets. Though its reputation suffered a bit from its shock defeat of Saving Private Ryan at the 1998 Oscars, now that the wound has healed, we can appreciate it for the uplifting period epic that it is.
How to watch: Shakespeare in Love is now streaming on Max.
13. Batman Returns
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The best Batman movie of them all! Period. Do not pass go, do not collect 200 Miss Kitties. Max has all the other Bat-candidates streaming — Tim Burton’s original, the Nolan trilogy, the Schumacher one-off, plus Matt Reeves’ fresh 2022 take with Robert Pattinson — so feel free to test that assertion, but I stand by it. Where else are you gonna get Michelle Pfeiffer purring in patent leather? A soiled Danny DeVito biting a man’s nose off? A cascade of sexual perversions masquerading as a routine superhero flick, Batman Returns bewildered the unsuspecting public when it came out in 1992. But it was formative for an entire generation of queer kids to be, and we’re still cat-whipping ourselves to completion with an umpteenth Christmas-time rewatch. Never forget: Mistletoe can be deadly if you eat it, but a kiss can be even deadlier if you mean it, baby.* — Jason Adams, Entertainment Reporter
How to watch: Batman Returns is now streaming on Max.
14. Leaving Las Vegas
Nicholas Cage won an Academy Award for his unflinching portrayal of Ben Sanderson, an alcoholic screenwriter who heads to Las Vegas, determined to drink himself to death. There, he meets Elisabeth Shue, who is spellbinding as a prostitute with a heart of gold.
As you can probably surmise, this one’s not for family movie night. Or fun, happy movie night. But it’s the perfect pick for relentlessly-dark-and-impossibly-human movie night. Leaving Las Vegas is a stark, honest depiction of addiction and self-destruction that is both brutal and beautiful.
How to watch: Leaving Las Vegas is now streaming on Max.
Never forget that Reese Witherspoon wasn’t always America’s beaming sweetheart. In Alexander Payne’s vicious high school political satire, she’s Tracy Flick, the terrifyingly ambitious overachiever willing to do whatever it takes to win the race for student body president. Matthew Broderick shook off the long shadow of Ferris Bueller to play the embittered teacher who just can’t stand to see her sail to the success she thinks she deserves, and slowly drives himself mad trying to get in her way. More than 20 years (and several bruising election cycles) later, its edges are as sharp as ever.* — Caitlin Welsh, Entertainment Reporter
How to watch: Election is now streaming on Max.
16. The Matrix
The Matrix has been imitated, referenced, and parodied so frequently in the past two decades, it’s almost easy to forget how mind-blowing it once felt. Almost. Watch the real thing in 2021, and it’s still plain to see that Lana and Lilly Wachowski’s sci-fi thriller is a true original. Keanu Reeves stars as Neo, a computer programmer haunted by the sense that something’s just off — only to be proven right when he discovers he’s been living in a simulation all along. The Wachowskis weren’t the first to raise the idea that reality might not be real (and there are other, less literal ways to interpret that central concept), but The Matrix did so with such panache that it forever embedded it into our pop culture consciousness. The sequels may not have the sterling reputation as the original, but they’re also worth watching for the Wachowskis’ unparalleled action sequences and trippy philosophizing — and they’re on Max, too.* — Angie Han, Deputy Entertainment Editor
How to watch: The Matrix is now streaming on Max.
17. Wayne’s World
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Wayne’s World has had a truly indelible effect on popular culture. It introduced “Schwing!” into the vernacular, made “That’s what she said” a household joke, and the scene of Wayne and Garth headbanging to “Bohemian Rhapsody” remains one of cinema’s most iconic moments to this day. Inspired by an SNL sketch and produced by Lorne Michaels, Wayne’s World is a charming and often absurd comedy that perfectly encapsulates the carefree hope of the early ’90s. Also, it’s downright hilarious.
Mike Myers and Dana Carvey are Wayne and Garth, two long-haired, grungy, rock music lovers who host a public access television show in Wayne’s parents’ basement. When a slick producer (Rob Lowe) offers to buy the show, they jump at the chance to make their dreams come true. But these two free thinkers find having a boss and working for the man might not be worth the money that comes with it. Silly, fun, and much smarter than it looks, Wayne’s World is a delightful ’90s nostalgia-fest that feels as fresh and engaging as if it were made yesterday.
How to watch: Wayne’s World is now streaming on Max.
Even if you haven’t seen 1990’s Ghost, you know about the pottery scene. It’s simply too iconic! You can’t go a year on this earth without seeing some sort of new parody or reference to the world’s more famous sensual potting wheel rendezvous — and it’s been a full three decades since the movie debuted! But there’s more to this movie than sexy ceramics. It’s a supernatural romance with thriller elements tied in, and it’s about as swoon-worthy as a love story can get.
When Sam Wheat (Patrick Swayze) is murdered, he is surprised to find himself still tethered to earth as a ghost. He must do everything he can to try and save his artist girlfriend (Demi Moore) from the man who killed him, but the only person who can see him is a quack psychic (a fantastic Whoopi Goldberg).
How to watch: Ghost is now streaming on Max.
19. Edward Scissorhands
The most “Tim Burton” of all Burton films, featuring the most “Johnny Depp” of all Depp roles, Edward Scissorhands is an insane and endearing story about a sheltered teen who, well, his fingers are scissors. He’s got scissorhands. It’s right there in his name!
No one could ever love such a strange and potentially dangerous boy, right? He’ll never be accepted by a white-picket fence, all-American community, right?! Wrong, not when Winona Ryder is in the cast!
Intentionally strange and macabre, and just oozing with heart and vulnerability, Edward Scissorhands is an offbeat family film about misfits, and a welcome hug for anyone who has ever felt like they didn’t belong.
How to watch: Edward Scissorhands is now streaming on Max.
20. Star Trek: First Contact
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While the quality of Star Trek films has run the gamut from campy romps to action epics over the years, Star Trek: First Contact is universally regarded as one of the best. Featuring the Next Generation crew helmed by legendary captain Jean-Luc Picard (Patrick Stewart), the USS-Enterprise faces a new threat from the Borg, cybernetic villains who have traveled back in time to conquer Earth from the past. Now, Picard and his crew must journey to the 21st century to stop the Borg from assimilating the human race and obliterating the future as we know it. Exciting, emotional, and a gripping tale of revenge, First Contact completely revived the flagging Star Trek franchise in its 1996 debut.
How to watch: Star Trek: First Contact is now streaming on Max.
21. Funny Games
Despair, thy name is Michael Haneke.
This 1997 home-invasion thriller cemented the acclaimed Austrian director as someone keenly interested in human brutality. It’s not just that Funny Games involves horrific acts, which are often performed with a harrowing shrug or off-screen, but that it wallows in the rippling outward effects that they have. Thus, the plight of the tormented characters bleeds through the screen, reflecting our indifference and our numbness in participating in this world.
Ulrich Mühe, Susanne Lothar, and Stefan Clapczynski star as a family of three who go on what should be a carefree lakeside vacation. But almost immediately, they are interrupted by two disturbingly polite and well-mannered young men (Arno Frisch and Frank Giering), who say they’re friends of the neighbors. And before you know it, the neighborly act of borrowing some eggs has descended into horror.
Callous and as cruel as they come, Funny Games is built to make you furious, squirming in your helplessness, and boy, does it ever.* — J.A.
How to watch: Funny Games is now streaming on Max.
22. Batman: Mask of the Phantasm
Batman: Mask of the Phantasm is the only traditionally animated Batman movie to get a theatrical release. It is also a masterpiece of ’90s Batman storytelling. In Mask, which takes place outside the canon of Batman: The Animated Series but is created by the same team, another side of Bruce Wayne’s origin story emerges when he meets a childhood friend at his family’s grave and falls for her. This rare love story reframes Bruce’s later transformation into Batman as a horrific choice to abandon his chance at a normal life and actively embrace the tortured life of a vigilante, a choice that comes back to haunt him years later in the form of the mysterious villain The Phantasm. — Alexis Nedd, Senior Entertainment Reporter
23. Pulp Fiction
In the almost 30 years since Pulp Fiction hit theaters, Quentin Tarantino has become many things to many people — but Pulp Fiction remains some of his best work. Based on the violence and rapport of pulp novels and magazines, the film follows Vincent (John Travolta) and Jules (Samuel L. Jackson) in various chapters of their life of crime. But if you’ve seen Pulp Fiction or been vehemently told to, you know this isn’t a film for story. It’s a film you watch for structure, for style, for self-awareness and genre-bending and the alchemical pairing of Travolta and Jackson. The only itch you can scratch in watching Pulp Fiction is wanting to watch Pulp Fiction — and for that, nothing else comes close. — Proma Khosla, Entertainment Reporter
How to watch: Pulp Fiction is now streaming on Max.
UPDATE: Jan. 16, 2024, 4:00 p.m. EST This story was updated to reflect the latest offerings on Max.