When you think back to the '90s, it may seem difficult to name a fantastic year for movies. But if we look at the final year of the decade, 1999 churned out a surprising amount of iconic movies.
Sure, there were plenty of cheesy, forgettable movies to come out of 1999 as well. But there are some true gems that haven't lost their luster. Here are the best movies of 1999 according to Rotten Tomatoes.
Boys Don't Cry (88%)
Hilary Swank made herself a true Hollywood star in her career-changing role as Brandon Teena in Boys Don't Cry. Though the film was not a huge box office success, it garnered Swank an Oscar for Best Actress and a nomination for Chloe Sevigny for Best Supporting Actress.
The film wasn't without its share of controversy with a brutal rape scene and sex scene that had to be toned down to escape the death knell of an NC-17 rating. It continues to be a divisive movie to this day, but it certainly will not be forgotten.
The Matrix (88%)
The Matrix certainly wasn't Keanu Reeves' first action film, but it became his most iconic (that is until the John Wick series reminded everyone how good he is at this). The sequels, The Matrix Reloaded and The Matrix Revolutions were met with mixed responses, but the first still holds up after 20 years.
It would be endlessly parodied throughout the 2000s and has seen more than its fair share of memes in the 2010s. If you somehow have missed this, go do yourself a favor and watch it wherever you can find it.
Election (92%)
Election may not be Reese Witherspoon's most remembered film, but it certainly hasn't disappeared from the cultural landscape. It even received its own Criterion release last year. Witherspoon stars as Tracy Flick, a young woman seeking the nomination of student body president.
When she announces her intentions to run to one of her teachers, Jim McAllister, the hijinks ensue. The film wouldn't go on to be a huge box-office success, but it did receive its fair share of acclaim. And if director Alexander Payne is to be believed, it is Barack Obama's favorite political film.
Being John Malkovich (93%)
Spike Jonze took Hollywood by storm in his first feature-length film, Being John Malkovich. Set partly in the real world, partly in the head of John Malkovich, Craig Schwartz (John Cusack) finds a portal to John Malkovich's head from the office where he works.
The results are exactly what you might expect from a script from Charlie Kaufman. It may not have skyrocketed anyone else's career besides Jonze, but it didn't get completely ignored come Oscar season.
Princess Mononoke (93%)
Though Princess Mononoke was the highest-grossing film of 1997 in Japan, it would take a few more years before it made a splash in the United States.
Sadly, the Best Animated Picture category of the Oscars didn't exist just yet, so it went largely unnoticed in that regard here. But it has been re-released several times in the U.S. in both 2018 and 2019, managing to pull in a little over $1 million with each release. Not too shabby for a movie that's been out for two decades!
American Movie (94%)
Bet you haven't heard of this one! One of the most intriguing documentaries to come out of the '90s was American Movie. The doc follows a young filmmaker, Mark Borchardt, trying to put his short film "Coven" together and to say that everything that can go wrong does go wrong is an understatement.
In some ways, it is also a love letter to burgeoning filmmakers everywhere. It is surprising that for that reason alone the film didn't get more awards outside of winning the Grand Jury Prize for Documentary at Sundance.
Three Kings (94%)
If you were hired to cast a trio for an offbeat heist comedy today, you probably wouldn't think to combine Marky Mark, Ice Cube, and George Clooney. But in 1999, they did just that. Clooney, Cube, and Mark play soldiers who, at the conclusion of the Gulf War, decide to go on a hunt for golden bullion stolen from Kuwait.
Directed by David O. Russell, the film received some controversy due to John Ridley not receiving a screenwriting credit. The film wasn't a huge success at the box office, grossing just $107.7 million against a $75 million budget.
The Iron Giant (96%)
Director Brad Bird's first feature-length animated film would go on to bomb at the 1999 box office, but it has since become a cult classic. Some would even argue it's his best film. The story is set in 1957 shortly after the Cold War, a giant robot lands on earth to be discovered by a young boy whose wildest dreams of having a robot friend have come true.
But, it has also set off the alarms for federal agencies desperate to ensure that it will not be a bigger threat. Featuring Vin Diesel (pre-Fast and Furious days) in the titular role, The Iron Giant holds up better than more than a few of 1990s animated films.
The Straight Story (96%)
When you think of David Lynch, you probably don't think of this movie. And yet, not only is it directed by him; it is his highest rated film on Rotten Tomatoes. Though Lynch has referred to it as his "most experimental film", it is perhaps his most accessible.
The Straight Story tells the true story of Alvin Straight, who, upon hearing of his brother's failing health decides to go visit him. And he doesn't take a plane, train, or automobile. Instead, he opts for a John Deere tractor to make the 240-mile journey. It may not be easy to find anymore, but it is definitely worth the watch.
Toy Story 2 (100%)
It is a pretty rare accomplishment for a film to achieve a 100% Fresh score on Rotten Tomatoes; it's even rarer for a sequel to obtain it. Toy Story 2 defied the odds and did just that. When Woody gets stolen at a garage sale, Buzz and the rest of the toys go to save him. Two more sequels followed but had the franchise ended with this entry, it still would have been a perfect duo of films. It was when Woody first faced his mortality and realized what he wanted to do most with the time he had left with Andy. You can love TS3 & TS4 all you want, but they are essentially chasing the same ideas planted in TS2.