Top 20 Of 1999

I go by US Theatrical release date so some of the dates IMDB lists are wrong. They go by the first release date of any country.
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1.
Fight Club (1999)
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  
An insomniac office worker, looking for a way to change his life, crosses paths with a alter-ego devil-may-care soap maker, forming an underground fight club that evolves into something much, much more... (139 mins.)
Director: David Fincher
 
2.
The Matrix (1999)
    1 2 3 4 5 6 7 8 9 10 8.7/10 X  
A computer hacker learns from mysterious rebels about the true nature of his reality and his role in the war against its controllers. (136 mins.)
 
3.
Magnolia (1999)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
An epic mosaic of interrelated characters in search of love, forgiveness, and meaning in the San Fernando Valley. (188 mins.)
 
4.
SLC Punk! (1998)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
In the early 1980s Stevo and Heroin Bob are the only two dedicated punks in conservative Salt Lake City. (97 mins.)
Director: James Merendino
 
5.
10 Things I Hate About You (1999)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A pretty, popular teenager can't go out on a date until her ill-tempered older sister does. (97 mins.)
Director: Gil Junger
 
6.
Boys Don't Cry (1999)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Female-born Teena Brandon adopts his male identity of Brandon Teena and attempts to find himself and love in Nebraska. (118 mins.)
Director: Kimberly Peirce
 
7.
Girl, Interrupted (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Based on writer Susanna Kaysen's account of her 18-month stay at a mental hospital in the 1960s. (127 mins.)
Director: James Mangold
 
8.
Toy Story 2 (1999)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
When Woody is stolen by a toy collector, Buzz and his friends vow to rescue him, but Woody finds the idea of immortality in a museum tempting. (92 mins.)
 
9.
American Beauty (1999)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend. (122 mins.)
Director: Sam Mendes
 
10.
Run Lola Run (1998)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
After a botched money delivery, Lola has 20 minutes to come up with 100,000 Deutschmarks. (81 mins.)
Director: Tom Tykwer
 
11.
Being John Malkovich (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich. (112 mins.)
Director: Spike Jonze
 
12.
Lock, Stock and Two Smoking Barrels (1998)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A botched card game in London triggers four friends, thugs, weed-growers, hard gangsters, loan sharks and debt collectors to collide with each other in a series of unexpected events, all for the sake of weed, cash and two antique shotguns. (107 mins.)
Director: Guy Ritchie
 
13.
The Talented Mr. Ripley (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
In late 1950s New York, Tom Ripley, a young underachiever, is sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled millionaire playboy. But when the errand fails, Ripley takes extreme measures. (139 mins.)
 
14.
The Minus Man (1999)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
A cold-blooded serial killer floats around the country and chooses his victims from people who complain... (111 mins.)
Director: Hampton Fancher
 
15.
The Sixth Sense (1999)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A boy who communicates with spirits that don't know they're dead seeks the help of a disheartened child psychologist. (107 mins.)
 
16.
Eyes Wide Shut (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A New York City doctor, who is married to an art curator, pushes himself on a harrowing and dangerous night-long odyssey of sexual and moral discovery after his wife admits that she once almost cheated on him. (159 mins.)
Director: Stanley Kubrick
 
17.
The Insider (1999)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A research chemist comes under personal and professional attack when he decides to appear in a "60 Minutes" expose on Big Tobacco. (157 mins.)
Director: Michael Mann
 
18.
Any Given Sunday (1999)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them. (162 mins.)
Director: Oliver Stone
 
19.
Pushing Tin (1999)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A feud develops between two air traffic controllers: one cocky and determined while the other is restrained and laidback, which inevitably affects their lives. (124 mins.)
Director: Mike Newell
 
20.
Man on the Moon (1999)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
The life and career of a legendary comedian, Andy Kaufman. (118 mins.)
Director: Milos Forman