Artisan Entertainment/20th Century Fox
By some accounts, 1999 was the best year for movies there ever was. It was certainly a very good one. Its high quality was complemented by a wide variety of popular titles. There were movies like The Matrix, which broke records at the box office, and smaller releases like Eyes Wide Shut that nonetheless made a huge impact. It was a pivotal year in the history of Hollywood before the franchises of today played a huge role in box office success.
Of course, that wasn't totally true. After all, 1999 was the year Toy Story 2 came out, and it was also the first chance for fans to take a look at the Star Wars prequels. For the most part, though, 1999 was a just a great year for every kind of movie. There were era-defining films in every genre. It was a year of life-changing movies. Here are 20 movies released in 1999 that we're still watching 20 years later. Who knows if any movies released this year will have the same legacy?
Buena Vista Pictures
10 Things I Hate About You not only launched Heath Ledger into stardom, it also capped a decade filled with great teen movies. The film, which follows a rude young woman who is manipulated into a relationship by her younger sister, is still a classic. It's the kind of movie that doesn't really get made anymore.
There are still plenty of great teenage romantic comedies, of course. 10 Things I Hate About You is an adaptation of Taming of the Shrew, though. You don't see mainstream movies reworking classical works of literature that often today, and honestly, that's more of a loss than it might seem.
The Matrix is a movie that is very much of its time. It's about a time where nothing is exactly what it seems, and it creates a very specific, very fascinating world. There are few movies as distinct as The Matrix, which is part of the reason the movie was such a smash.
Although the investment definitely paid off, The Matrix was a risky proposition on paper. It's a totally original idea filled with philosophical concepts on martial arts. It could have been a total disaster. Because the Wachowskis were allowed to follow through on their vision, though, they turned it into a tremendous success.
For most of the '90s, Julia Roberts and Hugh Grant were two of the world's biggest stars. It's fitting, then, that as the decade drew to a close, they came together. In Notting Hill, Julia plays a famous American actress who disrupts the quiet existence of Hugh's bookish character.
From there, the two carry on an affair that forces them to reckon with their different lifestyles. In a decade filled with great romantic comedies, Notting Hill stands as one of the very best. It's a reminder of the charm these movies can have when they're done expertly and have magnetic stars at their center.
20th Century Fox
This movie was not exactly a success, but it was a game-changer. The first Star Wars prequel was one of the most anticipated movies ever. Unfortunately, many fans were left baffled by what they saw. This was not the Star Wars they knew and love.
This is one of the few movies on this list that changed lives for the worse. It ruined a lot of people's perceptions of Star Wars as a brand. Of course, it also proved that more sequels were economically viable. It's likely why new films are being released so regularly today, so that's one positive that comes from Phantom Menace.
There were plenty of movies about sex before American Pie, but something shifted when this movie hit theaters. Following a group of young virgins who decide it's time for that to change, the film was unafraid of being frank about sex. American Pie's sense of humor was just a little bit different from most of what had come before it.
It was a little broader, a little grosser, and a little bit more outrageous. Part of the fun of this movie and the sequels that it spawned was how much it all felt like a dare. Most of the time, you couldn't believe what you were looking at.
The Blair Witch Project redefined an entire genre of film. After its release, horror movies underwent something of a transformation. The found footage genre became a huge force not just in horror, but across all subjects, as well.
The movie is also unique because of how well it performed against its tiny budget. It was an example of an indie movie that did enormous business and was ultimately a runaway success. Movies don't have to be big investments to make a ton of money. That's a lesson that many in Hollywood seem to have forgotten in today's era of mega-budget blockbuster fare.
Speaking of sex, Stanley Kubrick's final film isn't exactly subtle in its exploration of a sexually frustrated marriage. Most of the '90s were good to Tom Cruise, but 1999 was an especially good year for him. In this movie, he gets to reveal a whole new side of himself. He's vulnerable and obsessive.
As he discovers an entirely new world, he's forced to reckon with his relationship with his wife, played by Nicole Kidman. The fact that the two were a couple at the time only complicates the film. There are a million different ways to look at Eyes Wide Shut, and all of them are fascinating.
The Iron Giant was another animated marvel from 1999. It launched director Brad Bird into superstardom, and also made more than a few people cry. The film works mostly because it's telling a fairly simple story. It's E.T., but with a giant robot.
Every aspect of the film is perfectly designed, and every story element seems perfectly calibrated. It's a movie that both kids and adults can watch and love. Brad would eventually become known for his ability to balance those two qualities in Pixar films. Before he did that, though, he showed off his incredible set of skills on The Iron Giant.
1999 was a great year for twist films, and The Sixth Sense may have been the very best of the bunch. If by some miracle, you don't know the twist, I won't spoil it here. Suffice it to say that the twist at this movie's center made director M. Night Shyamalan famous for twists for the rest of his career.
It's easy to understand why that's the case. The Sixth Sense is a hugely effective film. It's tense and terrifying, and also moving where it needs to be. Although the rest of the director's career didn't turn out perfectly, this classic has stood the test of time.
Even 1999 was not without its fair share of remakes. The original Thomas Crown Affair came out in 1968, but this remake isn't without value of its own. Starring Pierce Brosnan as a bored millionaire who steals paintings for the thrill, the film is a light, fun thriller about rich people behaving badly.
Those kinds of movies have a slightly different tone today, but it's worth noting that Michael B. Jordan is set to star in another remake of this film. Some stories don't really age or can be adapted to different times. The Thomas Crown Affair is apparently one such story.
A lot of the movies released in 1999 had a certain attitude. Of those, Fight Club is probably the best example. It's a movie about sticking it to the man, and the depression that comes with materialism. It's meant to be a very edgy film, and in many ways it is.
It also features an iconic performance from Brad Pitt in one of the film's central roles. Fight Club is an incredibly stylish movie that's skeptical of authority in all of its forms. It's a movie about a lost generation that doesn't have anything to fight for. As a result, they fight themselves.
Three Kings is one of the less famous movies on this list, but it's also one of the best. It's from David O. Russell, who went on to direct Silver Linings Playbook and American Hustle. Before those films, though, O. Russell made this war satire about three Gulf war soldiers who try to steal massive amounts of gold.
The film has great performances from George Clooney and Mark Wahlberg. It's also a fascinating blend of styles and ideas that create an entirely new sensibility about war. It's not a straight-up war film, but it knows when to take war seriously and when to make fun of it.
Boys Don't Cry changed people's perceptions. It's rare for a movie to accomplish that, but this one did. In its empathetic portrayal of an actual transgender man, the film was a lot of people's first exposure to that topic.
20 years later, it can be hard to believe that there wasn't a time when these things were discussed openly. In 1999, there were large parts of America that ignored the issue entirely. Thanks to this film, and a magnificent performance from Hillary Swank, that changed. The change wasn't huge, of course. Perceptions change gradually and then all at once. This movie was one step in that process.
Michael Mann's The Insider may not be the director's best-known work, but it's one of his very best films. Following a former tobacco company employee who tries to prove how much the companies know about the harmful effects of cigarettes, the film is a fascinating true story about what it means to be complicit.
It's almost a game of cat and mouse, as a reporter tries to cultivate the former employee as a source. The Insider is a thrilling film about what corporations will hide in pursuit of profit. It's one of the very best movies Michael has ever made and a really engaging thriller.
Although not everyone appreciated director Kevin Smith's Dogma when it was first released, it has been reevaluated in recent years. The film, which follows two angels who want to destroy humanity to return to heaven, is delightfully off-kilter. It's the kind of movie that feels dated but not at all in a negative way.
It also takes perfect advantage of Matt Damon and Ben Affleck at the peak of their star power. Dogma is not a particularly subtle film, but it is a deeply effective one. Kevin knows how to write abrasive, witty dialogue, and he uses that ability to full effect here.
Toy Story was a hugely important film. It signaled the arrival of Pixar and an entirely new era of computer-generated animation. There was a lot of pressure on that film's sequel to deliver, and it met and exceeded those expectations.
Toy Story 2 is pretty much perfect. It may even be an improvement upon the original, and it's certainly more tear-inducing. It's a movie about mortality and obsolescence, and it handles both of those ideas with a surprising amount of clarity. All of that wrapped up in a kids' movie.
Another major star in the '90s was Tom Hanks, and The Green Mile was how he chose to end the decade. Following Hanks's portrayal of a security guard as he encounters a unique prisoner who seems to have supernatural abilities, the film resonated with audiences in a big way.
The Green Mile is a film that works as an allegory, but also as a tale of one man's suffering. On the surface, it's a story about judging people based on their appearance. Underneath that, though, it's a fascinating look at the brutalities of criminal justice, and how the system can chew up innocent, kind people.
New Line Cinema
Director Paul Thomas Anderson has probably made more iconic films in his career, but Magnolia might be his weirdest effort. The film is kaleidoscopic, giving characters the chance to bounce off of one another in random ways. The characters at the film's center are connected to one another but often indirectly.
Most movies that take that approach feel forced or cliched. Magnolia works only because Paul has such a distinct, weird vision. The cast is filled with great performances, but Tom Cruise is the film's standout. He delivers the movie's biggest heartbreaking moment and takes on one of only a few roles that reflect back on his own persona.
The Talented Mr. Ripley is disturbing, but deeply compelling. It's a movie about obsession and jealousy, and it's a perfect vehicle for a side of Matt Damon we don't see very often. It also makes perfect use of Jude Law, who looks like the perfect human specimen in the role.
The movie had a fairly big run at the Oscars, but its cultural legacy has lasted even longer. The Talented Mr. Ripley is a quiet thriller about a man pretending to be someone else. What's thrilling about it, though, is how specific every choice the movie makes is from its very first moment.
Galaxy Quest rules. It's one of the funniest movies ever made, and it's also a perfect parody of the world of Star Trek. The miracle of the film is that it works at all. Following Tim Allen as a William Shatner-esque figure who is now a has-been, Galaxy Quest takes him and the rest of his show's cast on an actual intergalactic adventure.
The supporting cast for the film is stellar. From Sigourney Weaver to Tony Shalhoub to Alan Rickman to Sam Rockwell, there's not a bad performance in the bunch. Galaxy Quest is one of the most delightful movies ever made.