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August 2009
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Top Ten Films From 1999

It’s been 10 years since 1999. It is a year that will be remembered for the Y2K scare and the Columbine shootings, a time of upheaval with everyone on the brink of panic. Or at least some of those extremes. The films of the time definitely reflected the era, with The Matrix and American Beauty among the top earners of the year. But this year is more remembered for the films that didn’t break the box office records, for the movies that had real staying power and still feel relevant today. Here’s my list of the Top Ten films from 1999. It’s totally subjective and in no particular order:


Fight Club

This movie is among my favorites of all time. The look of the film, the voice over narration done perfectly by Edward Norton, and the big twist at the end, this movie’s got it all. It reflected the apocalyptic feel of 1999 and the anti-consumerism sentiment that was prevalent since the mad spending of the 1980s and before the bubble burst.


Toy Story 2

Pixar was still new at this point and didn’t have the audiences guaranteed. They deserve every single one of their fans, myself included. The film follows the story of childhood lost, teaching us to hold on to what we have when we have it, and just appreciate it while it lasts. There’s nothing better in life than making people happy, and Pixar does that with every film they make.



It’s hard to believe MTV used to make quality films like this. The story of Tracy Flick is still relevant today – just look at Hillary Clinton and Sarah Palin. Women in power, and how they got there, hold the attention of America because it is still a rarity (sadly). Plus, this is the film that broke Reese Witherspoon into Hollywood, and she has continued to prove her acting chops since.


The Sixth Sense

M. Night Shamalyan has never been able to live up to the quality of his first film. Seeing this movie for the first time, the tension and the scares kept me on the edge of my seat. It’s a good horror story without being about blood and gore and the ending will live in film history as one of the best twists.


10 Things I Hate About You

It’s kind of sad to watch now, since Heath Ledger’s untimely passing, but it’s still one of my favorite teen flicks. It took Shakespeare and made it hip and relatable by being barely recognizable. But still, a great movie with a talented cast that went on to play other great roles and make a name for themselves in Hollywood: Heath Ledger, Joseph Gordan-Lovitt, and Julia Stiles. Plus, it has one of my favorite film moments in it, which you can watch in the video above.



My favorite of Kevin Smith’s films (followed closely by Mallrats), follows two fallen angels as they try to get back into God’s good graces. The cast is hilarious, as they are in every other Kevin Smith movie, but the way this film skewers religion while not fully insulting it and its followers is something more movies should learn. Also, the casting of God was a stroke of genius.


Galaxy Quest

As a Star Trek fan since the womb, I know a thing or two about sci fi shows and conventions. This lovingly mocks the whole world, but doesn’t do it maliciously. It’s funny and snarky, without being mean. For anyone who’s even touched upon the sci fi lifestyle, I recommend watching this movie for a laugh.


The Matrix

What can I say about this movie? It changed the entire way action scenes were shot! It had great action, a mind bending plot, and was perfectly cast with Keanu Reeves. He does that confused thing so well. This movie stands the test of time, yet still reflects the sentiment of 1999. Just ignore the sequels, and we’ve got ourselves a new classic.


October Sky

This is the movie that made me fall in love with Jake Gyllenhaal. It’s an inspirational tale, based on a true story of course, about 4 small town boys who use science and rocket building to escape their coal mining town. They did it without proper help from their school, with just their own motivation to keep them chugging along.


Office Space

Everyone loves this movie. It may not have been a box office smash, but everyone I know has seen it and likely owns the dvd. I didn’t appreciate this movie when it came out, but now that I’m in the working world, I can definitely see its appeal. It’s a hilarious film about surviving the office and the mindnumbing work that comes with it.


Did I leave off any of your 1999 favorites? What do you think of these ten films?

About Kristal Bailey

With a soft spot for movies that fall into the “So Bad They’re Good” category, Kristal Bailey regularly watches B-movies, 80s comedies, and sci-fi from the 50s and 60s. She also refuses to grow up if that means she has to hide her love for Disney and Pixar films. In her free time, she enjoys reading graphic novels or books that are soon to be turned into movies, watching hours and hours of television, and spending way too much time on Twitter.


  1. Snorple the Minimonkey says:


  2. ea says:

    I'm a noted apologist for "The Mummy" and (I'm about to go there) "Star Wars–Episode 1: The Phantom Menace," but I doubt both of them would make my personal top ten.

    The only glaring omission here is "South Park: Bigger, Longer, and Uncut"–still wildly entertaining a decade later and one of the finest satires of the past 30 years. "Three Kings" is pretty freaking great, as is "Beyond the Mat," a heartwrenching doc about pro wrestlers long before Mickey Rourke was doing the Ram Jam.

    Props on "Galaxy Quest" and "October Sky." Watching Jake Gyllenhaal descend into the coal mines on that elevator was the saddest Jake Gyllenhaal moment I have ever seen, narrowly beating out the part in "Brokeback Mountain" where he's incapable of selling tractors.

  3. Kristal says:

    Hi Charles! Thanks for the follow!

    and ea, that elevator scene breaks me everytime. So much is sad with no words. I actually haven't seen "Three Kings" and never even heard of "Beyond the Mat". I'll have to add them to my netflix and check them out. Thanks for the comment!