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American Beauty (1999)

Summary: A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.

Release Date: October 01, 1999

Genre: Drama

Director: Sam Mendes

Writer: Alan Ball

Runtime: 2 h 02 min

MPAA: R

Production: Dreamworks Pictures, Jinks/Cohen Company

Distributor: DreamWorks Distribution, DreamWorks Home Entertainment, American Broadcasting Company (ABC)

Country: United States

Language: English

Movie budget: $ 15,000,000

Domestic: $ 130,096,601

International: $ 226,200,000

181 - Rotten Tomatoes

Fight Club (1999)

Summary: An insomniac office worker and a devil-may-care soap maker form an underground fight club that evolves into much more.

Release Date: October 15, 1999

Genre: Drama

Director: David Fincher

Writers: Chuck Palahniuk

, Jim Uhls

Runtime: 2 h 19 min

MPAA: R

Production: Fox 2000 Pictures, New Regency Productions, Linson Films, Atman Entertainment, Knickerbocker Films, Taurus Film

Distributor: Twentieth Century Fox, 20th Century Fox Home Entertainment, Tubi TV

Countries: Germany, United States

Language: English

Movie budget: $ 63,000,000

Domestic: $ 37,030,102

International: $ 64,290,907

171 - Rotten Tomatoes

Toy Story 2 (1999)

Summary: When Woody is stolen by a toy collector, Buzz and his friends set out on a rescue mission to save Woody before he becomes a museum toy property with his roundup gang Jessie, Prospector, and Bullseye.

Release Date: November 24, 1999

Genres: Adventure, Comedy, Animation

Directors: John Lasseter

, Ash Brannon

, Lee Unkrich

Writers: John Lasseter

, Pete Docter

, Ash Brannon

Runtime: 1 h 32 min

MPAA: G

Production: Pixar Animation Studios, Walt Disney Pictures

Distributor: Buena Vista Home Entertainment, American Broadcasting Company (ABC), Disney Channel, Toon Disney, Disney Digital 3-D, Walt Disney Studios Motion Pictures, ABC Family, Disney XD

Country: United States

Language: English

Franchise: Toy Story

Movie budget: $ 90,000,000

Domestic: $ 245,852,179

International: $ 251,523,202

169 - Rotten Tomatoes

The Blair Witch Project (1999)

Summary: 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.

Release Date: July 30, 1999

Genres: Horror, Mystery

Directors: Daniel Myrick

, Eduardo Sánchez

Writers: Daniel Myrick

, Eduardo Sánchez

, Heather Donahue

Runtime: 1 h 21 min

MPAA: R

Production: Haxan Films

Distributor: Artisan Entertainment, Artisan Home Entertainment, HBO Max, Lions Gate Films Home Entertainment, Lionsgate Home Entertainment

Country: United States

Language: English

Franchise: Blair Witch

Movie budget: $ 60,000

Domestic: $ 140,539,099

International: $ 108,100,000

160 - Rotten Tomatoes

Eyes Wide Shut (1999)

Summary: A Manhattan doctor embarks on a bizarre, night-long odyssey after his wife's admission of unfulfilled longing.

Release Date: July 16, 1999

Genres: Drama, Thriller, Mystery

Director: Stanley Kubrick

Writers: Stanley Kubrick

, Frederic Raphael

, Arthur Schnitzler

Runtime: 2 h 39 min

MPAA: TV-MA

Production: Warner Bros., Stanley Kubrick Productions, Hobby Films, Pole Star

Distributor: Warner Bros., Warner Bros. Domestic Television Distribution, Warner Home Video

Countries: United Kingdom, United States

Language: English

Movie budget: $ 65,000,000

Domestic: $ 55,691,208

International: $ 106,593,627

160 - Rotten Tomatoes

The Matrix (1999)

Summary: When a beautiful stranger leads computer hacker Neo to a forbidding underworld, he discovers the shocking truth--the life he knows is the elaborate deception of an evil cyber-intelligence.

Release Date: March 31, 1999

Genres: Action, Sci-Fi

Directors: Lana Wachowski

, Lilly Wachowski

Writers: Lilly Wachowski

, Lana Wachowski

Runtime: 2 h 16 min

MPAA: R

Production: Warner Bros., Village Roadshow Pictures, Groucho Film Partnership, Village Roadshow Pictures, Silver Pictures, 3 Arts Entertainment

Distributor: Warner Bros., Fox Network, HBO Max, Peacock, Studio Distribution Services (SDS), Warner Bros. Home Entertainment

Countries: United States, Australia

Language: English

Franchise: The Matrix

Movie budget: $ 63,000,000

Domestic: $ 172,076,928

International: $ 295,763,521

149 - Rotten Tomatoes

Magnolia (1999)

Summary: An epic mosaic of interrelated characters in search of love, forgiveness and meaning in the San Fernando Valley.

Release Date: December 25, 1999

Genre: Drama

Director: Paul Thomas Anderson

Writer: Paul Thomas Anderson

Runtime: 3 h 08 min

MPAA: 18A

Production: Ghoulardi Film Company, New Line Cinema, The Magnolia Project

Distributor: HBO Max

Country: United States

Language: English

Movie budget: $ 37,000,000

Domestic: $ 22,455,976

International: $ 25,997,565

145 - Rotten Tomatoes

The World Is Not Enough (1999)

Summary: James Bond uncovers a nuclear plot while protecting an oil heiress from her former kidnapper, an international terrorist who can't feel pain.

Release Date: November 19, 1999

Genres: Action, Adventure, Crime

Director: Michael Apted

Writers: Neal Purvis

, Robert Wade

, Bruce Feirstein

Runtime: 2 h 08 min

MPAA: PG-13

Production: Danjaq, Eon Productions, Metro-Goldwyn-Mayer (MGM), Danjaq, United Artists

Distributor: Metro-Goldwyn-Mayer Distributing Corporation (MGM), CBS, Sony Pictures Home Entertainment, 20th Century Fox Home Entertainment, Warner Bros. Home Entertainment

Countries: United Kingdom, United States, Spain

Language: English

Franchise: James Bond

Movie budget: $ 135,000,000

Domestic: $ 126,943,684

International: $ 234,888,716

143 - Rotten Tomatoes

The Iron Giant (1999)

Summary: A young boy befriends a giant robot from outer space that a paranoid government agent wants to destroy.

Release Date: August 06, 1999

Genres: Action, Adventure, Animation

Director: Brad Bird

Writers: Tim McCanlies

, Brad Bird

, Ted Hughes

Runtime: 1 h 26 min

MPAA: PG

Production: Warner Bros., Warner Bros. Animation, Warner Bros. Feature Animation

Distributor: Cartoon Network, HBO Max, Nickelodeon Network, PBS Kids Sprout, The WB Television Network, Warner Home Video

Countries: United States, Czechia, United Kingdom, Czech Republic

Language: English

Movie budget: $ 70,000,000

Domestic: $ 23,315,035

International: $ 22,596

137 - Rotten Tomatoes

The Green Mile (1999)

Summary: Paul Edgecomb, the head guard of a prison, meets an inmate, John Coffey, a black man who is accused of murdering two girls. His life changes drastically when he discovers that John has a special gift.

Release Date: December 10, 1999

Genres: Drama, Fantasy, Crime

Director: Frank Darabont

Writers: Stephen King

, Frank Darabont

Runtime: 3 h 09 min

MPAA: R

Production: Castle Rock Entertainment, Darkwoods Productions, Warner Bros.

Distributor: American Broadcasting Company (ABC), HBO Max, Studio Distribution Services (SDS), Warner Bros. Home Entertainment, Warner Home Video

Country: United States

Language: English

Movie budget: $ 60,000,000

Domestic: $ 136,801,374

International: $ 150,000,000

137 - Rotten Tomatoes

The Insider (1999)

Summary: A research chemist comes under personal and professional attack when he decides to appear in a 60 Minutes exposé on Big Tobacco.

Release Date: November 05, 1999

Genres: Drama, Thriller, Biography

Director: Michael Mann

Writers: Marie Brenner

, Eric Roth

, Michael Mann

Runtime: 2 h 37 min

MPAA: R

Production: Touchstone Pictures, Forward Pass, Blue Lion Entertainment, Digital Image Associates, Kaitz Productions, Mann/Roth Productions, Spyglass Entertainment

Distributor: Buena Vista Pictures, Touchstone Home Video, Touchstone Home Entertainment

Country: United States

Language: English

Movie budget: $ 90,000,000

Domestic: $ 29,089,912

International: $ 31,200,000

136 - Rotten Tomatoes

The Talented Mr. Ripley (1999)

Summary: In late 1950s New York, a young underachiever named Tom Ripley is sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled millionaire playboy. But when the errand fails, Ripley takes extreme measures.

Release Date: December 25, 1999

Genres: Drama, Crime, Thriller

Director: Anthony Minghella

Writers: Patricia Highsmith

, Anthony Minghella

Runtime: 2 h 19 min

MPAA: R

Production: Miramax, Paramount Pictures, Mirage Enterprises, Timnick Films

Distributor: Paramount Pictures, HBO Max, National Broadcasting Company (NBC), Warner Home Video

Country: United States

Language: English

Movie budget: $ 40,000,000

Domestic: $ 81,298,265

International: $ 56,733,167

134 - Rotten Tomatoes

Being John Malkovich (1999)

Summary: A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich.

Release Date: December 03, 1999

Genres: Comedy, Drama, Fantasy

Director: Spike Jonze

Writer: Charlie Kaufman

Runtime: 1 h 53 min

MPAA: R

Production: Astralwerks, Gramercy Pictures (I), Propaganda Films

Distributor: Universal Studios, The Criterion Collection

Country: United States

Language: English

Movie budget: $ 13,000,000

Domestic: $ 22,863,596

International: $ 243,199

131 - Rotten Tomatoes

Wild Wild West (1999)

Summary: The two best special agents in the Wild West must save President Grant from the clutches of a diabolical, wheelchair-bound, steampunk-savvy, Confederate scientist bent on revenge for losing the Civil War.

Release Date: June 30, 1999

Genres: Action, Comedy, Sci-Fi

Director: Barry Sonnenfeld

Writers: Jim Thomas

, John Thomas

, S.S. Wilson

Runtime: 1 h 46 min

MPAA: PG

Production: Peters Entertainment, Sonnenfeld Josephson Worldwide Entertainment, Todman, Simon, LeMasters Productions, Warner Bros.

Distributor: Warner Bros., Warner Home Video, CBS, HBO Max

Country: United States

Language: English

Movie budget: $ 170,000,000

Domestic: $ 113,804,681

International: $ 108,300,000

129 - Rotten Tomatoes

Three Kings (1999)

Summary: In the aftermath of the Persian Gulf War, four soldiers set out to steal gold that was stolen from Kuwait, but they discover people who desperately need their help.

Release Date: October 01, 1999

Genres: Action, Adventure, Comedy

Director: David O. Russell

Writers: John Ridley

, David O. Russell

Runtime: 1 h 54 min

MPAA: R

Production: Warner Bros., Village Roadshow Pictures, Village-A.M. Partnership, Junger Witt Productions, Witt/Thomas Productions

Distributor: HBO Max, National Broadcasting Company (NBC), Warner Home Video

Countries: United States, Australia

Language: English

Movie budget: $ 75,000,000

Domestic: $ 60,652,036

International: $ 47,100,000

128 - Rotten Tomatoes

Dogma (1999)

Summary: An abortion clinic worker with a special heritage is called upon to save the existence of humanity from being negated by two renegade angels trying to exploit a loop-hole and reenter Heaven.

Release Date: November 12, 1999

Genres: Adventure, Comedy, Drama

Director: Kevin Smith

Writer: Kevin Smith

Runtime: 2 h 10 min

MPAA: R

Production: View Askew Productions, STK

Distributor: Lions Gate Films, Columbia TriStar Home Entertainment, Columbia TriStar Home Video, Comedy Central, Sony Pictures Entertainment (SPE)

Country: United States

Language: English

Franchise: View Askewniverse

Movie budget: $ 10,000,000

Domestic: $ 30,652,890

International: $ 778,006

128 - Rotten Tomatoes

American Pie (1999)

Summary: Four teenage boys enter a pact to lose their virginity by prom night.

Release Date: July 09, 1999

Genre: Comedy

Directors: Paul Weitz

, Chris Weitz

Writer: Adam Herz

Runtime: 1 h 35 min

MPAA: 18A

Production: Universal Pictures, Zide-Perry Productions, Newmarket Capital Group

Distributor: Fox Network, HBO Max, Peacock, Universal Studios Home Video

Country: United States

Language: English

Franchise: American Pie

Movie budget: $ 11,000,000

Domestic: $ 102,561,004

International: $ 132,922,000

127 - Rotten Tomatoes

Any Given Sunday (1999)

Summary: A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them.

Release Date: December 22, 1999

Genres: Drama, Sport

Director: Oliver Stone

Writers: Daniel Pyne

, John Logan

, Oliver Stone

Runtime: 2 h 42 min

MPAA: R

Production: Warner Bros., Ixtlan, Donners' Company

Distributor: Warner Bros., American Broadcasting Company (ABC), HBO Max, Warner Home Video

Country: United States

Language: English

Movie budget: $ 55,000,000

Domestic: $ 75,530,832

International: $ 24,700,000

126 - Rotten Tomatoes

Galaxy Quest (1999)

Summary: 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. However, they also have to defend both Earth and the alien race from a reptilian warlord.

Release Date: December 25, 1999

Genres: Adventure, Comedy, Sci-Fi

Director: Dean Parisot