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  1. News
  2. ›Best Movies Ever

The 15 Greatest Movies of 1999, 20 Years Later

Jesse Schedeen
September 11, 2019 - 1 min read

1999 was a great year for film, whether you prefer groundbreaking horror flicks, family-friendly animated fare or blockbuster action movies. Here are 15 classics that easily stand the test of time two decades later.

'All About My Mother'

Pedro Almodovar delivered one of his best films ever in 1999, one that earned a well-deserved Academy Award for Best Foreign Language Film. This drama focuses on a group of women dealing with different emotional crises, somehow managing to avoid becoming trite and melodramatic in the process.

'Audition'

1999 was a truly transformative year for horror. "Audition" played its part by helping to expose Western viewers to the amazing work being done by Japanese directors, as well as (for better or worse) paving the way for the rise of the torture porn sub-genre.

'Being John Malkovich'

Among other things, 1999 is the year we learned what a winning combination director Spike Jonze and writer Charlie Kaufman are. This comedy manages to be hilarious, clever and completely unpredictable all at once. It also proves that there's no better character for John Malkovich to play than himself.

'The Blair Witch Project'

Like it or not, 1999 was the year found footage horror roared back with a vengeance. And it's all thanks to this ultra low-budget movie. "The Blair Witch Project" makes the most of its clever premise, proving terrifying enough that plenty of moviegoers were absolutely convinced they were watching a true documentary.

'Bringing Out the Dead'

Nic Cage really needs that right combination of material and director to shine, and he definitely found it in "Bringing Out the Dead." With Martin Scorsese directing and Paul Shraeder writing and Cage himself playing a burnt out paramedic, this one definitely leaves a lasting impression.

'Eyes Wide Shut'

Sadly, 1999 was the year that legendary director Stanley Kubrick passed away. But at least Kubrick was able to complete "Eyes Wide Shut" and give the movie world one last masterpiece. Beautifully shot and hauntingly bleak, this sexually charged drama makes the most of the chemistry between stars (and former husband and wife) Tom Cruise and Nicole Kidman.

'Fight Club'

"Fight Club" may well be the most quoted movie of 1999, even 20 years later. Love or hate the film's philosophy on modern civilization and manhood, there's no denying that this is a visually stunning film. Plus, Brad Pitt and Edward Norton make a great team.

'The Insider'

For a few years it seemed like Russell Crowe was the toast of the awards circuit, and you can trace that back directly to his starring role in this Michael Mann drama. A fictionalized account of the story of tobacco industry whistleblower Jeffrey Wigand, "The Insider" makes the most of Mann's keen directorial vision, Crowe's rugged charisma and Al Pacino's Pacino-ness.

'The Iron Giant'

If there's a clear contender for the best non-Disney or Pixar animated movie of the '90s, it's this one. "The Iron Giant" delivers a winning blend of gorgeous animation, epic B-movie action and a totally charming tale of a lonely boy befriending a gigantic robot from outer space. We've all been there.

'Magnolia'

If anyone in Hollywood was having a good year in 1999, it was Tom Cruise. Not only did he star in Stanley Kubrick's final completed film, he also appeared in this critically beloved ensemble drama from P.T. Anderson. "Magnolia" is a challenging but ultimately very rewarding look at a group of interconnected lives in the San Fernando Valley.

'The Matrix'

Few films from 1999 have had such a lasting and significant impact on the film industry. "The Matrix heralded a new era for action movies, blending stylized kung-fu, philosophy, cyberpunk and revolutionary special effects into one thrilling whole.

'The Mummy'

We're honestly not sure why Universal has had such a tough go of revamping their monster movie properties. "The Mummy" did it so well back in 1999. No only is this action/adventure romp a worthy update to the original, it's a far better Indiana Jones sequel than "Kingdom of the Crystal Skull."

'The Sixth Sense'

Rounding out a year of great horror in 1999 was "The Sixth Sense," a movie that simultaneously revived Bruce Willis as a leading man and put director M. Night Shyamalan on the map. It was and still is a very smartly crafted horror movie that retains its impact even 20 years later, even long after everyone learned about that incredible twist ending.

'The Straight Story'

"The Straight Story" is pretty much the last thing you'd expect from a director like David Lynch, but that's partly why it works so well. Lynch plays against type for this rural drama about an elderly farmer traveling the countryside on his tractor. Lynch's keen eye and the top-notch cast really make this movie sing.

'Toy Story 2'

Disney dropped plenty of animated sequels in the '90s, but most of them were direct-to-video dreck that utterly failed to live up to the originals. Thankfully, "Toy Story 2" finally came along to show that these sequels don't have to be cheap, disposable fare. Rather, it managed to top the first "Toy Story" in pretty much every area.

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Best Movies EverMoviesWorth Watching
Jesse Schedeen
Article by Jesse Schedeen
Freelance Writer

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