The '90s were a pretty amazing decade for film. The rom-com (opens in new tab) was at its pinnacle (Pretty Woman, You've Got Mail), comedies were truly funny (Home Alone, Groundhog Day), critical faves were also crowd-pleasers (Titanic, Forrest Gump), horror films (opens in new tab) were bone-chilling and realistic (The Silence of the Lambs, Se7en) and teen comedies were having a heyday (10 Things I Hate About You, Clueless), making the years 1990 to 1999 a particularly good time to go to the movies if you were a teenager. Maybe it's because going to the movies was still a thing in the '90s? Also, raise your hand if you made a weekly run to the local Blockbuster to grab that week's entertainment.
Luckily for you, most of these flicks can be watched now, in 2022, from the comfort of your couch via Netflix and other streaming services. We've scoured the archives and rounded up the best '90s films with the most iconic characters—from Mrs. Doubtfire to Hannibal Lecter to Cher Horowitz—and we've listed them here for you. Or, if you've never seen these movies but are looking for a new decade of films to obsess over, these are the ones to binge immediately. The next lazy Saturday you have, why not take a stroll down memory lane with these iconic, nostalgic films?
'Ghost' (1990)
Pottery class became sexy after this romantic thriller starring Demi Moore and Patrick Swayze. The pair plays a loved-up couple whose relationship is cut short when Sam (Swayze) is murdered. As his spirit wanders the Earth, he learns Molly (Moore) could have the same fate and must somehow warn her before it's too late.
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'Empire Records' (1995)
So quintessentially '90s you'll be in awe, Empire Records had a little bit of everything that made the era great (and, well, not so great). There's killer music, breakout performances from before-you-knew-them stars (hey, Renee Zellweger!), and impeccable fashion that looks totally new again nearly 30 years on. Who cares that this movie has like ten plots? Immerse yourself in the nostalgia.
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'The Best Man' (1999)
The Best Man was important for a lot of reasons (summarized nicely in this E! article (opens in new tab)), primarily because it was a long-overdue romance and damn good movie starring Black actors. It also portrayed everyday struggles and successes: "African American people being people, as opposed to stereotypes," as Taye Diggs put it. It was a star-making movie for a number of super-talented actors (Diggs! Nia Long! Harold Perrineau! Regina Hall! Just to name a few!) and even though it's a deeply 90s movie, there's so much to love.
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'The Parent Trap' (1998)
Identical twins Annie and Hallie (Lindsay Lohan) never knew the other existed until they crossed paths at summer camp. The only logical response? Trade places so they can meet their other parent for the first time while simultaneously getting the 'rents back together somehow. Forever thankful to director Nancy Meyers for casting Dennis Quaid as their father.
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'Friday' (1995)
Recently unemployed Craig (Ice Cube) finds himself in a bind when he and his buddy Smokey (Chris Tucker) have to come up with $200 in one day. More than 20 years later, this film will make you laugh until your stomach hurts.
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'Romeo + Juliet' (1996)
Hollywood may reboot the classic Shakespeare play every few years, but this one starring Claire Danes and a young Leonardo DiCaprio reigns supreme. Sure, you know the ending, but the modern twist on this classic tale has a few tricks up its sleeve you won't see coming.
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'The Joy Luck Club' (1993)
Based on the bestselling 1989 novel written by Amy Tan, The Joy Luck Club is a tear-jerker tale between four first-generation Chinese-American women and their mothers. It was the first film of its kind to feature an all-Asian cast, something that wouldn't be seen again until (opens in new tab)the release (opens in new tab) of Crazy Rich Asians in 2018. Bring lots of tissues and get ready to call your mom when the credits start to roll.
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'Never Been Kissed'
Drew Barrymore stars as a reporter going undercover in a local high school to try to redeem the terrible experience she had the first time around. A movie that has the trappings and joy of a rom-com in a plot that gets weirder the more you think about it (and if you want to enjoy it, don't dwell on the highly questionable relationship Josie has with her English teacher, who is unaware that she's actually an adult). Despite all that, it weirdly holds up!
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'The Talented Mr. Ripley' (1999)
The dark themes in the movie (um, a poor man ingratiates himself into a rich man's social circle, becomes obsessed, and—spoiler alert—murders the guy?) are offset by the fact that the movie is just so stylish and sexy. The setting and the lavish lifestyle of the young and wealthy, combined with the gorgeous actors swanning around in linen, makes this film just as beautiful as it is macabre.
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'Elizabeth' (1998)
All hail Cate Blanchett. This is an absolute tour-de-force performance (Blanchett was only 29 at the time!) of the ascension of Queen Elizabeth. It's got a lot of surprisingly resonant themes: the pressures of a woman to get married, the constant onslaught of men trying to tell her what to do, a very sexy boyfriend (Joseph Fiennes) who ends up being kind of a douchebag. She's the 16th century feminist we love to see on our screens.
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'Men In Black' (1997)
Think F.B.I, but for out-of-this-world monsters. Fortunately for James Edwards (Will Smith) of the N.Y.P.D., they're looking for recruits. Unfortunately for James, he has no idea what he signed up for, but it's up to him and his partner "K" (Tommy Lee Jones) to save the Earth from some super creepy aliens before it's too late.
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'Half Baked' (1998)
The quintessential stoner comedy and a cult classic to boot, Half Baked follows three stoners in New York as they try to earn enough money to bail their friend out of jail for accidentally killing a police horse. It's actually even weirder than that, but it really works when the viewer is in, ahem, a specific state of mind.
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'Sliding Doors' (1998)
A cool premise executed perfectly: what if one small, seemingly meaningless decision changes your entire life? Gwyneth Paltrow's Helen misses a train—no wait, she totally catches it. She stays with her douchebag boyfriend—no, she catches him cheating and dumps him! And so on. It's a really compelling film start to finish (and a bit depressing until the very end, TBH), and Paltrow nails both the happy and unhappy Helen, with an instantly iconic haircut. It's a perfect piece of pop psychology, too.
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'Schindler's List' (1993)
Schindler's List is based on the true story of industrialist Oskar Schindler (Liam Neeson), who, with the help of his wife (Caroline Goodall), saved more than 1,200 Jews by employing them in his factories during World War II. It earned Steven Spielberg his first Oscar win for Best Director and would take home six other Academy Awards.
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'Mission: Impossible' (1996)
There's a reason they made seven films and counting. Ethan Hunt (Tom Cruise, who else?) is a secret agent disavowed by his organization after losing his entire team of spies. On the run, he's forced to complete a dangerous mission for an arms dealer. OTT plot aside, it's also an excuse for Cruise to do cool stunts, like hang from ceilings and from the top of trains—and this is the beginning of that trend.
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'Hook' (1991)
Steven Spielberg has a knack for getting us right in the feelings, and Hook is a masterclass. Robin Williams stars as a grown-up Peter Pan who has forgotten his role as the leader of the Lost Boys in Never Never Land and grown into his role as a well-to-do lawyer. But when his kids get kidnapped by Captain Hook, he has to sprinkle on some fairy dust and go rescue them. Sweet, charming, tear-jerkingly moving? Check, check, and check.
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'The Bodyguard' (1992)
Forever icon Whitney Houston made her debut in this romantic thriller alongside Kevin Costner as a famous pop singer who hires a former Secret Service agent to be her bodyguard. It gets hot and also terrifying super quick. Don't even get us started on the soundtrack! It's still the bestselling soundtrack album (opens in new tab) of all time, with more than 42 million certified copies sold worldwide.
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'Se7en'
It's not necessarily an easy watch (and the movie gets reduced to the What's in the booooox? meme more often than not), but it's an incredibly tense, well-acted, riveting drama that doubles as a compelling whodunit. The film actually improves the more you watch it. Also, it has a young and hot Brad Pitt. So.
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'Romy and Michele's High School Reunion' (1997)
Former high school losers, unite!! In this offbeat, wacky, heartfelt movie, Romy and Michele try not to get bullied at their high school reunion by pretending they invented Post-Its. What starts as a wacky comedy of errors turns into a kind of refreshing take on just letting your true weirdness shine through.
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'Muriel's Wedding' (1994)
Toni Collette stars in this cult classic about a painfully awkward young woman in a small town in Australia who, tired of feeling disconnected from her life, decides to steal some money from her parents and go on a vacation. Things spiral out of control quickly, as she moves to the city, marries an Olympic star for money, and even finds herself along the way.
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'The Piano' (1993)
Mother-daughter duo Ada (Holly Hunter) and Flora (Anna Paquin) arrive at New Zealand's North Island with a handful of items, including a prized piano, to meet Ada's new husband, Stewart (Sam Neill). The relationship soon goes south when Stewart sells the piano to a neighbor name George (Harvey Keitel), who tells her she can earn the instrument back by teaching him how to play and some other things. Things get steamy...quickly!
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'Sister Act' (1992)
This film (and to a lesser extent its sequel) has so many things going for it. A charismatic Whoopi Goldberg performance. Gorgeous songs. Hilarious religious hijinks?? In the iconic original, lounge singer Deloris is put into witness protection in a run-down San Francisco convent, and transforms their choir into an absolute powerhouse.
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'Selena' (1997)
J. Lo's breakout role was to play the Tejano music star Selena Quintanilla-Pérez in a biopic about her life and tragic death at 23. The songs are gorgeous, the performance is heartfelt, the story's important and resonant. For weeks afterwards you'll find yourself singing "Dreaming of You" at the top of your lungs.
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'The Birdcage'
Robin Williams plays a gay cabaret owner in Miami who convinces his drag queen partner (played by Nathan Lane) to pose as a woman when their son announces he's engaged to the daughter of a conservative senator. It's funny, warm, and (while it probably wouldn't be made quite this way nowadays, given that it has mostly straight actors playing gay characters) surprisingly progressive for the time period, showing that there's no one way a loving family has to look.
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'The Truman Show' (1998)
Hundreds of tiny cameras have been watching Truman Burbank's (Jim Carrey) every move for close to 30 years as a part of an extreme 24/7 reality show called The Truman Show. Except he doesn't know he's the main character of this real-but-fictional world...until he finds out the hard way.
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'Out of Sight' (1998)
U.S. marshal tries to take down criminal. Criminal charms U.S. marshal. Extreme sexiness ensues. Another exceptional early J. Lo performance, this is also a classic, star-making vehicle for George Clooney playing a stylish con man. It's not the only time this kind of story's been told, but with Steven Soderbergh directing, it's definitely one of the best.
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'Shawshank Redemption' (1994)
Stephen King's 1982 novella Rita Hayworth and Shawshank Redemption finally saw the big screen in this Oscar-nominated story of two inmates serving a life sentence at one of the country's harshest prisons, documenting their tight-knit relationship over many years. It's longer than most films, and devastating in its themes, but you'll treasure every minute.
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'American Pie' (1999)
Vulgar, insensitive, and yet oddly endearing, American Pie ushered in a whole new level of teen comedies when it explored the difference between how young women and young men view sex in the 1990s. While not all of its cinematic progeny are winners (the world would have been OK without Van Wilder), it was groundbreaking at the time and still gets some hearty laughs today.
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'The Sandlot' (1993)
The baseball movie of all baseball movies focuses on a group of kids and the adventure-filled summer they shared in 1962. Terrifying dogs, battling neighborhood bullies, treehouse sleepovers, and one crush on a lifeguard awaits! Also, 99 percent sure everyone's first crush was on Benny "The Jet" Rodriguez (Mike Vitar) because of this film, so we thank The Sandlot for its service!
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'Before Sunrise' (1995)
Suddenly the idea of meeting your soulmate on a train ride heading from Budapest to Vienna, spending one glorious night together, and falling deeply in love seems possible after watching this movie. Just me? Okay! If you don't believe me, there are two more films in this series that say otherwise so, yeah, get those tissues ready,
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'Thelma and Louise' (1991)
When Ridley Scott's thrilling adventure of two best friends on the run hit theaters in the summer of 1991, we were forever changed. It was one of the first movies I saw that showed me all things women could (and had been doing) without the over-looming guidance of males. The bond Geena Davis and Susan Sarandon share is nothing short than perfection. Also, speaking of perfection (for the second time on this list), we get a shirtless 26-year-old Brad Pitt, so no complaints here.
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'Babe' (1995)
Another one of those '90s movies that, on paper, shouldn't work and yet the end result is genius. Babe is a weird little movie about a talking pig who finds his way to Farmer Hoggett's sheep farm and, after his border collie surrogate mother teaches him how to be a herding pig, finds his true calling. Why am I crying?
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'Jerry Maguire' (1996)
Tom Cruise, Cuba Gooding Jr., and Reené Zelleweger showed us the money in this instant classic from legendary journalist Cameron Crowe. The script about a uber-successful sports agent who has an epiphany and decides to start all over took Crowe five years to write. (opens in new tab)The time was well spent since it earned him an Oscar nomination for Best Screenplay at the 1997 Academy Awards.
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'Four Weddings and a Funeral' (1994)
Oh, 1994, what a time to be alive! We were first really introduced to unbelievably charming Hugh Grant, and nothing was the same. The story of a man who realizes he might have found his soulmate (Andie MacDowell) after running into each other at five different social events is set to make any heart a little bit bigger. We may have came for the love story, but we really stayed for Hugh Grant's hair.
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'Boogie Nights' (1997)
Director Paul Thomas Anderson put himself on the map with the 1997 film about the pornography industry in the late 70s and early 80s. We relished in Burt Reynolds' mustache, gasped at Mark Wahlberg's prosthetic penis, and just couldn't take our eyes away from the screen until the credits rolled. The craziest thing of all about the film isn't even in the picture: Leonardo DiCaprio was going to play Dirk Diggler (opens in new tab) but had to turn it down because he was filming Titanic. He then suggested Wahlberg for the role.
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'Fargo' (1996)
The story of a husband who hires two criminals to kidnap his wife so he can receive the large ransom from his wealthy father-in-law was unforgettable in 1996. The crime movie that mixed in comedy put the Coen Brothers on the map and won Joel Coen the Best Director Award at the Cannes Film Festival the same year. I mean it got Frances McDormand her Oscar! It also inspired a spin-off series of the same name that premiered on FX in 2014 that was equally great.
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'Porco Rosso'
Studio Ghibli's only other movie from the 1990s didn't get its flowers stateside until the 2000s, when it received a good English dub and a DVD release over a decade after it first hit theaters in Japan. It follows the story of a 1930s fighter pilot, racked with PTSD from the first World War, who was mysteriously (and inexplicably, though there are hints) turned into a talking pig bounty hunter battling sky pirates. What can we say, the '90s was a great time for talking pigs. It's also a moving meditation on war, aviation, and travel—with gorgeous animated scenes of the Dalmatian coast—and is a low-key contender for one of the top Hayao Miyazaki creations.
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'Tommy Boy' (1995)
The '90s to Chris Farley are like peanut butter and jelly. They just go together. When Tommy Boy came out, Farley was finishing up his fifth and final year at Saturday Night Live, and would we miss him. The comedy about a loser son who has to try and take back the family business after his father's death with the help of an accountant (David Spade) is unforgettable. Yes, the movie may not be "critically acclaimed," but it represents the comedies of the decade so well.
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'Boyz N' The Hood' (1991)
John Singleton's debut 1991 film about three men growing up in the Crenshaw ghetto of Los Angeles put a narrative on America's screens that wasn't always seen. The breakout performance of Ice Cube alongside Cuba Gooding Jr. and Morris Chestnut as they come of age was a message worth taking note. Re-watching it now is a reminder of how Singleton's film was a risk worth taking.
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'Point Break' (1991)
Some people may shame us for putting this classic on this list, but we welcome you to embrace it. When you watch it and see not only Keanu Reeves but Patrick Swayze as shirtless surfers in Southern California, you will thank us. Watching Reeves as an FBI Agent undercover trying to find out who has been behind the recent burglaries in the area keeps me on the edge of my seat time after time.
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'Goodfellas' (1990)
It's the mob movies of all mob movies based on Nicolas Pileggi's best-selling novel (opens in new tab)Wiseguy (opens in new tab) about Henry Hill (Ray Liotta) and his rise and fall as a mobster in New York in the '60s and '70s without glorifying the violent behavior the occupation is known for. The six-time Oscar-nominated movie from Martin Scorsese may have debuted in 1990, but it would be talked about for the rest of the decade.
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'Shakespeare in Love' (1998)
The Best Picture Oscar winner for the year 1999, Shakespeare in Love stars Joseph Fiennes as the Bard himself, fallen on hard times and looking to score a hit with his new play, Romeo and Juliet. Meanwhile, Gwyneth Paltrow stars as a noblewoman with dreams of becoming an actress (at the time, women weren’t allowed to act and female parts were given to younger men in drag). Re-watching it now, this film is surprisingly progressive! It’s also still hot.
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'Sleepless in Seattle' (1993)
Sleepless in Seattle is as much a thinkpiece about romance movies as it is a romance movie in itself—and my goodness, it's a classic. The first pairing of '90s rom-com dynamos Meg Ryan and Tom Hanks, it's a film about loss, love, and fate—with as many brilliant one-liners as you'd expect from a Rob Reiner and Nora Ephron join.
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'The Sixth Sense' (1999)
To this day, the 1999 horror thriller by M. Night Shyamalan remains the be-all-end-all of twist endings. Though the director would never again have the monocultural filmmaking clout that he had in the wake of this film (I mean, how do you top an ending like this?!), this movie was everywhere for an entire year, and is still referenced today.
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'The Big Lebowski' (1998)
The Coen Brothers could have had no idea the impact their strange film The Big Lebowski would have had when it came out in 1998. I mean, how do you even sum up this plot? A slacker-y gentleman gets mixed up in a case of mistaken identity with a rich guy and his petulant young bride, and then have to go to war with some nihilists alongside his bowling buddies in down-and-out L.A.? Actually, yeah that’s pretty much what happens. Other stuff too, but if you’ve never seen it, you really ought to watch and figure out what everyone’s been quoting for the last 20 years. The Dude abides.
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'Rushmore' (1998)
The first Wes Anderson movie to really nail the director’s signature style. Sure, 1996’s Bottle Rocket is fantastic, but today feels like an outlier from Anderson’s later oeuvre—sorry for everything about that sentence, but it’s true! Jason Schwartzman stars as precocious, ambitious oddball Max, who is friends with the much older Bill Murray. The two of them eventually go head-to-head, however, when a pretty new teacher catches their eyes. The best scene, of course, is near the end when we see the fruits of Max’s playwriting labor in action.
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'Pretty Woman' (1990)
The movie that made Julia Roberts a star (and earned her a best actress Oscar nom in 1991). Vivian (Roberts) is a Hollywood prostitute hired as an escort by a wealthy businessman (Richard Gere), and over their week of social events and parties together, the two develop an unlikely love. The film’s script originally detailed (opens in new tab) the dark landscape of sex work in Los Angeles, but turned into a romantic comedy with a huge budget from Disney.
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'The Fifth Element' (1997)
Bruce Willis and Milla Jovovich star in this wacky sci-fi odyssey about a futuristic cab driver and the super smart alien he takes possession of in the 23rd century. Directed by Luc Besson, the vivid and bleakly believable (though not totally dystopian) imaginings about the human race's distant future are wildly engaging, and the film's overall strangeness has made it something of a classic.
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'Princess Mononoke' (1997)
An animated film from Studio Ghibli, this is the story of a world in which gods and humans live in harmony...until they don’t. When Ashitaka is bitten by a demon, she goes in search of a deer-god who can help her and ends up having an adventure. It was directed by the legendary anime director Hiyao Miyazaki, and remains one of the top-grossing anime films of all time.
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'Edward Scissorhands' (1990)
If you ever want to explain to someone from Gen Z why Tim Burton and Johnny Depp have worked together approximately a zillion times, all you have to do is show them Edward Scissorhands, which was the perfect marriage of the frequent collaborators' individual brands of creepy quirkiness in 1990.
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'Dazed and Confused' (1993)
Richard Linklater struck solid gold with Dazed and Confused: An ensemble comedy that was simultaneously goofy, nostalgic, and weirdly heartwarming at the same time. It’s about the last day of school for a 1970s Austin high school—and all the weird politics and sexual escapades that go into it. It’s a classic, and is filled with some of your favorite actors (hey Matthew McConaghey and Parker Posey!) doing some weird stuff. Oh, and the soundtrack is killer.
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'Home Alone' (1990)
Chris Columbus directs the outrageous movie of Kevin (Macaulay Culkin), a young boy mistakenly left at home—eating whatever he wants, contending with burglars—as his family flies to Paris for vacation. It was the highest-grossing live action comedy film in the United States of all time from its release in 1990 until 2011 (when The Hangover Part II overtook it).
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'Terminator 2: Judgment Day' (1991)
Rarely is a sequel more beloved than the original, but T2 is a classic of the action and science fiction genres. Not only were the special effects mind-blowing in 1991 (and still pretty good today, considering), but Linda Hamilton's Sarah Connor will go down in history as one of the most badass women in all of film.
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'Poetic Justice' (1993)
The 1993 romantic drama Poetic Justice stars Janet Jackson and Tupac Shakur, with an appearance by Maya Angelou. The film tells the story of Justice (Jackson), a hairdresser who writes and recites her own poems (actually written by Maya Angelou) throughout the film. The poems are Justice’s method of coping with the sudden murder of her boyfriend.
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'The Silence of the Lambs' (1991)
Dr. Hannibal Lecter (Anthony Hopkins) is an imprisoned psychiatrist, cannibal, and serial killer, whose insight and advice FBI trainee Clarice Starling (Jodie Foster) seeks for a new case. The psychological thriller is creepy AF, to say the least, but the movie is GOOD. The Silence of the Lambs (1991) is, at this point, the first and only horror film to win Best Picture.
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'Groundhog Day' (1993)
If you're ever looking for a hilarious comedy that doubles as a 101-minute thought experiment in philosophy, well, there's honestly only one movie to turn to, and that's Groundhog Day (1993), in which a curmudgeon-y weatherman is inexplicably caught in a time loop that forces him to live the same day over and over (and over) again for years on end.
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'Pulp Fiction' (1994)
This 1994 black comedy made up of several interwoven stories of characters involved in a world of crime and violence cemented Quentin Tarantino's popularity. Pulp Fiction is self-referential, out of chronological order, and entirely iconic. It stars John Travolta, Samuel L. Jackson, Uma Thurman, and Bruce Willis, and was nominated for seven Oscars.
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'Jurassic Park' (1993)
Jurassic Park, directed by Steven Spielberg in 1993, is set on an island turned into a park of cloned dinosaurs and... (Do you really not know what Jurassic Park is about? Or where we're going with this?) Anyway, the dinosaurs in the film were depicted with groundbreaking computer-generated imagery and the film was the highest-grossing film of all time until Titanic. It also spawned many, many sequels, which eventually led to this gif of Chris Pratt (opens in new tab).
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'Mrs. Doubtfire' (1993)
Robin Williams' character is recently divorced and missing his children, so he dresses up as a female housekeeper, whom he calls Mrs. Doubtfire, in an effort to be closer to them. The film—hilariously funny, witty, and iconic—was one of Williams’ greatest successes.
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'Forrest Gump' (1995)
This now-classic 1995 Best Picture winner takes audiences through the life of its titular character, the lovable—though slow—Forrest Gump (Tom Hanks). He runs across the country several times, meets Richard Nixon, serves in Vietnam, and teaches Elvis Presley to dance. Life is like a box of chocolates...
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'The Lion King' (1994)
The Lion King represents the peak of the Disney Renaissance and set box office records worldwide on its release. A clever retelling of Hamlet, the movie has as much drama and heart as its 2019 live-action film.
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'Clueless' (1995)
This 1995 modern retelling of Jane Austen's Emma centers on Cher (Alicia Silverstone): a superficial, attractive, wealthy 16-year-old in Beverly Hills. She plays matchmaker for teachers and students alike, gets dressed with an interactive carousel of clothing options, and conducts a makeover on a “tragically unhip” new girl. The movie was hugely influential (opens in new tab), even changing the lexicon of the American teenage girl—“As if!”
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'Toy Story' (1995)
The first-ever full-length Pixar tale changed the game for animated movies. The 1995 film, which told the story of what toys do when we leave the room (spoiler: come to life and exist in their own complex society), was groundbreaking and spawned several sequels, the latest one hit theaters in 2019.
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'Scream' (1996)
Scream is a horror classic and, when it was released, it turned the genre on its head and went meta before going meta was such a common move. It would go on to have three spin-off movies and be the go-to Halloween costumes for last-minute shoppers everywhere.
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'The Nightmare Before Christmas' (1993)
Tim Burton's claymation classic has stirred debate mainly for one central question it never satisfyingly answers: Is this a Christmas movie or a Halloween movie? Why not call it both and sit back, relax, and enjoy the gorgeous animation, thoughtful plot, and extremely catchy songs of this animated beauty.
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'Good Will Hunting' (1998)
20-year-old Will Hunting (Matt Damon) punches a police officer, is allowed deferred prosecution, and seeks therapy and mathematics tutoring from a renowned professor (Robin Williams). Ben Affleck and Matt Damon wrote the film together, and won an Academy Award for Best Original Screenplay. How do you like them apples?
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'10 Things I Hate About You' (1999)
A modernized, teenage-drama version of Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is about Cameron (Joseph Gordon-Levitt), who is in love with a girl (Larisa Oleynik) whose father won’t let her date until her older sister, intelligent, surly Kat (Julia Stiles), does. Cameron attempts to convince bad-boy Patrick (Heath Ledger) to take Kat out, and the two enter into an angsty, bittersweet romance.
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'You've Got Mail' (1998)
Following the success of 1993's Sleepless in Seattle, this delightful rom-com reunites Meg Ryan and Tom Hanks, two actors who have undeniable chemistry. It's a now-quaint-seeming story of two professional rivals who, unbeknownst to them, meet and fall in love via an online chat room. Written by Nora Ephron, they just don't make movies like this anymore.
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'The Blair Witch Project' (1999)
Written, directed, and edited by Daniel Myrick and Eduardo Sánchez, The Blair Witch Project is famously terrifying for its unique—and cheap—method of filming on handheld cameras. The film uses “recovered footage” from three student filmmakers who sought to document the local legend, the “Blair Witch,” and disappear in the process. The film premiered at the 1999 Sundance Film Festival with extreme success.
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'Fear and Loathing in Las Vegas' (1998)
The film, adapted from Hunter S. Thompson’s novel of the same name, failed both critically and financially at first, but has recently amassed a cult following. The story follows Raoul Duke (Johnny Depp) and Dr. Gonzo (Benicio del Toro) on a journalistic assignment that ends up being an exploration of Las Vegas under the influence of hallucinogenic drugs and copious other substances.
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'Fight Club' (1999)
The first rule of Fight Club is don't talk about Fight Club. ...But we're going to anyway: The unnamed protagonist, played by Edward Norton, is dissatisfied with his white-collar job, so he does what anyone in his position would: He starts a “fight club” for men who want to beat each other up recreationally. And there's a MAJOR twist. Though it was initially very polarizing, now, it’s a cult film and regarded as one of the best of the ‘90s.
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'Titanic' (1997)
This movie, which had most teenage girls sobbing their way through the late '90s, is a fictionalized account of the 1912 sinking of the RMS Titanic (obviously). It stars Leonardo DiCaprio at his heartthrob-iest and Kate Winslet, two passengers of vastly different social stature who fall in love during the Titanic’s first and final voyage. The 1997 film was nominated for 14 Academy Awards and won 11—including Best Picture and Best Director.
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'Austin Powers: International Man of Mystery' (1997)
Mike Meyers's goofy send-up of the secret agent genre is still quoted over 20 years on, and for good reason: It's extremely funny. Packed with stars and memorable characters, it's one of those satires that is so brilliant that it ends up making secret agent movies that came after it look sillier by comparison.
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'The Matrix' (1999)
In this dystopian future world, we exist in a simulated reality called “the Matrix,” and a couple of the main characters (Laurence Fishburne, Keanu Reeves) can enter and exit it. The Matrix has been critically acclaimed for its innovative visual effects and cinematography.
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