1999: The Top 50 Ranked (RottenTomatoes average rating)

According to average rating on RottenTomatoes.com, these are the 50 best films of 1999*

*RELEASED to a general American audience in 1999, not necessarily filmed/produced in 1999
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1.
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.)
 
2.
The Straight Story (1999)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
An old man makes a long journey by lawn-mover tractor to mend his relationship with an ill brother. (112 mins.)
Director: David Lynch
 
3.
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
 
4.
All About My Mother (1999)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
Young Esteban wants to become a writer and also to discover the identity of his father, carefully concealed by his mother Manuela. (101 mins.)
 
5.
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
 
6.
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
 
7.
The Iron Giant (1999)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A young boy befriends a giant robot from outer space that a paranoid government agent wants to destroy. (86 mins.)
Director: Brad Bird
 
8.
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
 
9.
The Winslow Boy (1999)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Early 20th century England: while toasting his daughter Catherine's engagement, Arthur Winslow learns... (104 mins.)
Director: David Mamet
 
10.
Topsy-Turvy (1999)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
After Gilbert and Sullivan's latest play is critically panned, the frustrated team threatens to disband until it is inspired to write the masterpiece "The Mikado". (154 mins.)
Director: Mike Leigh
 
11.
Three Kings (1999)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
In the aftermath of the Persian Gulf War, 4 soldiers set out to steal gold that was stolen from Kuwait, but they discover people who desperately need their help. (114 mins.)
 
12.
Election (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A high school teacher's personal life becomes complicated as he works with students during the school elections, particularly with an obsessive overachiever determined to become student body president. (103 mins.)
Director: Alexander Payne
 
13.
Princess Mononoke (1997)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
On a journey to find the cure for a Tatarigami's curse, Ashitaka finds himself in the middle of a war between the forest gods and Tatara, a mining colony. In this quest he also meets San, the Mononoke Hime. (134 mins.)
Director: Hayao Miyazaki
 
14.
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
 
15.
Tarzan (1999)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A man raised by gorillas must decide where he really belongs when he discovers he is a human. (88 mins.)
 
16.
October Sky (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes. (108 mins.)
Director: Joe Johnston
 
17.
Go (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Go! tells the story of the events after a drug deal, told from three different points of view. (102 mins.)
Director: Doug Liman
 
18.
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.)
 
19.
The Blair Witch Project (1999)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Three film students vanish after traveling into a Maryland forest to film a documentary on the local Blair Witch legend, leaving only their footage behind. (81 mins.)
 
20.
The War Zone (1999)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
An alienated teenager, saddened that he has moved away from London, must find a way to deal with a dark family secret. (98 mins.)
Director: Tim Roth
 
21.
The Limey (1999)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
An extremely volatile and dangerous Englishman goes to Los Angeles to find the man he considers responsible for his daughter's death. (89 mins.)
 
22.
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.)
 
23.
An Ideal Husband (1999)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Sir Robert Chiltern is a successful Government minister, well-off and with a loving wife. All this is... (97 mins.)
Director: Oliver Parker
 
24.
Open Your Eyes (1997)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A very handsome man finds the love of his life, but he suffers an accident and needs to have his face rebuilt by surgery after it is severely disfigured. (117 mins.)
 
25.
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.)
 
26.
Cookie's Fortune (1999)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Conflict arises in the small town of Holly Springs when an old woman's death causes a variety of reactions among family and friends. (118 mins.)
Director: Robert Altman
 
27.
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.)
 
28.
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 devil-may-care soap maker, forming an underground fight club that evolves into something much, much more. (139 mins.)
Director: David Fincher
 
29.
Liberty Heights (1999)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Anti-Semitism, race relations, coming of age, and fathers and sons: in Baltimore from fall, 1954, to fall... (127 mins.)
Director: Barry Levinson
 
30.
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
 
31.
Galaxy Quest (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
The alumni cast of a space opera television series have to play their roles as the real thing when an alien race needs their help. (102 mins.)
Director: Dean Parisot
 
32.
Notting Hill (1999)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
The life of a simple bookshop owner changes when he meets the most famous film star in the world. (124 mins.)
Director: Roger Michell
 
33.
The Red Violin (1998)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A perfect red-colored violin inspires passion, making its way through three centuries over several owners and countries, eventually ending up at an auction where it may find a new owner. (130 mins.)
 
34.
Limbo (1999)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
In an economically devastated Alaskan town, a fisherman with a troublesome past dates a woman whose young daughter does not approve of him. When he witnesses the murder of his shady brother, he, the woman and the kid run to the wilderness. (126 mins.)
Director: John Sayles
 
35.
The Hurricane (1999)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
The story of Rubin "Hurricane" Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence. (146 mins.)
Director: Norman Jewison
 
36.
Bowfinger (1999)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
When a desperate movie producer fails to get a major star for his bargain basement film, he decides to shoot the film secretly around him. (97 mins.)
Director: Frank Oz
 
37.
South Park: Bigger Longer & Uncut (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
When the four boys see an R-rated movie featuring Canadians Terrance & Phillip, they are pronounced "corrupted", and their parents pressure the United States to wage war against Canada. (81 mins.)
Director: Trey Parker
 
38.
Following (1998)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A young writer who follows strangers for material meets a thief who takes him under his wing. (69 mins.)
 
39.
Mansfield Park (1999)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
At 10, Fanny Price, a poor relation, goes to live at Mansfield Park, the estate of her aunt's husband... (112 mins.)
Director: Patricia Rozema
 
40.
Guinevere (1999)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A young girl from an affluent family rebels and becomes involved with a much older photographer. (104 mins.)
Director: Audrey Wells
 
41.
Trick (1999)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
The misadventures of two young gay men, trying to find a place to be alone, one night in Manhattan. (89 mins.)
Director: Jim Fall
 
42.
The Green Mile (1999)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
The lives of guards on Death Row are affected by one of their charges: a black man accused of child murder and rape, yet who has a mysterious gift. (189 mins.)
Director: Frank Darabont
 
43.
Sweet and Lowdown (1999)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman. (95 mins.)
Director: Woody Allen
 
44.
The Dinner Game (1998)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
To amuse themselves at a weekly dinner, a few well-heeled folk each bring a dimwit along who is to talk about his pastime... (80 mins.)
Director: Francis Veber
 
45.
Office Space (1999)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Three company workers who hate their jobs decide to rebel against their greedy boss. (89 mins.)
Director: Mike Judge
 
46.
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
 
47.
The Adventures of Elmo in Grouchland (1999)
    1 2 3 4 5 6 7 8 9 10 5.8/10 X  
Elmo loves his fuzzy, blue blanket, and would never let anything happen to it. However, a tug-of-war... (73 mins.)
Director: Gary Halvorson
 
48.
Bringing Out the Dead (1999)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Haunted by the patients he failed to save, an extremely burned-out Manhattan ambulance paramedic fights to maintain his sanity over three fraught and turbulent nights. (121 mins.)
Director: Martin Scorsese
 
49.
Happy, Texas (1999)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
Two escaped convicts arrive in the town of Happy, Texas, where they are mistaken for a gay couple who... (98 mins.)
Director: Mark Illsley
 
50.
eXistenZ (1999)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A game designer on the run from assassins must play her latest virtual reality creation with a marketing trainee to determine if the game has been damaged. (97 mins.)