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The Boondock Saints (1999)

Summary: Two Irish Catholic brothers become vigilantes and wipe out Boston's criminal underworld in the name of God.

Release Date: January 21, 2000

Genres: Action, Crime, Thriller

Director: Troy Duffy

Writer: Troy Duffy

Runtime: 1 h 48 min

MPAA: R

Production: Franchise Pictures, Brood Syndicate, Fried Films, B.D.S. Productions Inc., CB Productions

Distributor: 20th Century Fox Home Entertainment, Lions Gate Films Home Entertainment, South Boondock Productions

Countries: United States, Canada

Language: English

Movie budget: $ 6,000,000

Domestic: $ 30,471

61 - Rotten Tomatoes % Gap

Trippin' (1999)

Summary: The only effort high school student Greg Reed exerts is pursuing the beautiful and unattainable Cinny Hawkins. But when he realizes that that way to win Cinny's heart is through academics, Greg starts hitting the books.

Release Date: May 12, 1999

Genre: Comedy

Director: David Raynr

Writer: Gary Hardwick

Runtime: 1 h 34 min

MPAA: R

Production: Beacon Communications

Country: United States

Language: English

Movie budget: $ 3,000,000

Domestic: $ 9,017,070

57 - Rotten Tomatoes % Gap

Wirey Spindell (1999)

Summary: A whimsical look back at the life of a man who is nervous about his upcoming wedding.

Release Date: January 21, 2000

Genre: Comedy

Director: Eric Schaeffer

Writer: Eric Schaeffer

Runtime: 1 h 41 min

MPAA: Not Rated

Production: Five Minutes Before the Miracle, Terence Michael Productions, WinStar Cinema

Country: United States

Language: English

Domestic: $ 9,838

44 - Rotten Tomatoes % Gap

Love Stinks (1999)

Summary: Seth Winnick has it all: a successful career in television, good friends, and a passionate relationship with beautiful Chelsea. However, when he fails to make a timely marriage proposal, Chelsea tries to make his life hell.

Release Date: September 10, 1999

Genre: Comedy

Director: Jeff Franklin

Writer: Jeff Franklin

Runtime: 1 h 34 min

MPAA: R

Production: Baumgarten-Prophet Entertainment

Distributor: Independent Artists, Columbia TriStar Home Video

Country: United States

Language: English

Movie budget: $ 4,000,000

Domestic: $ 2,924,635

44 - Rotten Tomatoes % Gap

Plunkett & Macleane (1999)

Summary: Two robbers are persecuted by the law, whose servants are not much better and even worse.

Release Date: April 02, 1999

Genres: Action, Adventure, Comedy

Director: Jake Scott

Writers: Selwyn Roberts

, Robert Wade

, Neal Purvis

Runtime: 1 h 39 min

MPAA: R

Production: Arts Council of England, PolyGram Filmed Entertainment, Working Title Films

Country: United Kingdom

Language: English

Domestic: $ 474,900

43 - Rotten Tomatoes % Gap

Idle Hands (1999)

Summary: A teenage slacker's right hand becomes possessed with murderous intent.

Release Date: June 23, 1999

Genres: Comedy, Fantasy, Horror

Director: Rodman Flender

Writers: Terri Hughes Burton

, Ron Milbauer

Runtime: 1 h 32 min

MPAA: R

Production: Columbia Pictures, Licht/Mueller Film Corporation, Team Todd, TriStar Pictures

Distributor: Sony Pictures Entertainment (SPE), Columbia Pictures, Sony Pictures Releasing, Columbia TriStar Home Video, Scream Factory

Country: United States

Language: English

Movie budget: $ 25,000,000

Domestic: $ 4,152,230

International: $ 293

42 - Rotten Tomatoes % Gap

The Other Sister (1999)

Summary: A mentally challenged young woman seeks independence by obtaining her own apartment and attending college while her family plans her sister's wedding.

Release Date: February 26, 1999

Genres: Comedy, Drama, Romance

Director: Garry Marshall

Writers: Alexandra Rose

, Blair Richwood

, Garry Marshall

Runtime: 2 h 09 min

MPAA: PG-13

Production: Touchstone Pictures, Mandeville Films

Country: United States

Language: English

Movie budget: $ 35,000,000

Domestic: $ 27,807,627

41 - Rotten Tomatoes % Gap

Instinct (1999)

Summary: When noted anthropologist Dr. Ethan Powell, who left society to live in the jungle, is imprisoned for murder, it's up to young psychiatrist Theo Caulder to get through to him.

Release Date: June 04, 1999

Genres: Drama, Thriller

Director: Jon Turteltaub

Writers: Gerald Di Pego

, Daniel Quinn

Runtime: 2 h 06 min

MPAA: R

Production: Spyglass Entertainment, Touchstone Pictures

Distributor: Buena Vista Pictures, Buena Vista Home Entertainment, CBS

Country: United States

Language: English

Movie budget: $ 80,000,000

Domestic: $ 34,105,207

41 - Rotten Tomatoes % Gap

Julien Donkey-Boy (1999)

Summary: A portrait of the effects of schizophrenia on family life is the central focus.

Release Date: September 13, 2000

Genres: Comedy, Drama

Director: Harmony Korine

Writer: Harmony Korine

Runtime: 1 h 34 min

MPAA: R

Production: 391 Productions, Forensic Films, Independent Pictures (II)

Country: United States

Language: English

Domestic: $ 85,400

International: $ 7,042

41 - Rotten Tomatoes % Gap

A Dog of Flanders (1999)

Summary: Heartwarming story about an orphaned boy whose hard life is offset by his love for an abandoned dog, his determination to become a great painter, and his friendship with an artist.

Release Date: August 27, 1999

Genres: Drama, Family

Director: Kevin Brodie

Writers: Ouida

, Kevin Brodie

, Robert Singer

Runtime: 1 h 40 min

MPAA: PG

Production: Stonelock Pictures, Woodbridge Films

Distributor: Warner Bros.

Country: United States

Language: English

Movie budget: $ 7,000,000

Domestic: $ 2,165,637

41 - Rotten Tomatoes % Gap

Jawbreaker (1999)

Summary: Three of the most popular girls at Reagan High accidentally kill the prom queen with a jawbreaker when a kidnapping goes horribly wrong.

Release Date: August 01, 2022

Genres: Comedy, Crime, Thriller

Director: Darren Stein

Writer: Darren Stein

Runtime: 1 h 26 min

MPAA: 14A

Production: Crossroads Films, Jawbreaker Productions Inc., Kramer-Tornell Productions, TriStar Pictures

Distributor: TriStar Pictures, Music Television (MTV)

Country: United States

Language: English

Movie budget: $ 3,500,000

Domestic: $ 3,117,085

41 - Rotten Tomatoes % Gap

Stigmata (1999)

Summary: When a young woman becomes afflicted by stigmata, a priest is sent to investigate her case, which may have severe ramifications for his faith and for the Catholic Church itself.

Release Date: September 10, 1999

Genre: Horror

Director: Rupert Wainwright

Writers: Tom Lazarus

, Rick Ramage

Runtime: 1 h 43 min

MPAA: R

Production: Metro-Goldwyn-Mayer (MGM), FGM Entertainment, Instituto Nacional de Bellas Artes (INBA)

Distributor: Metro-Goldwyn-Mayer (MGM), Metro-Goldwyn-Mayer Distributing Corporation (MGM), MGM Home Entertainment, Scream Factory, Tubi TV

Countries: United States, Mexico

Language: English

Movie budget: $ 29,000,000

Domestic: $ 50,046,268

International: $ 39,400,000

40 - Rotten Tomatoes % Gap

Popular (1999)

Summary: Two girls who despise each other because they're on opposite sides of the "popularity fence" are forced together when the father of one of them marries the other's mother.

Release Date: September 29, 1999

Genres: Comedy, Drama, Romance

Runtime: 1 h 00 min

MPAA: TV-14

Production: Murphy/Matthews Productions, Shephard / Robin Productions, Touchstone Television

Country: United States

Language: English

39 - Rotten Tomatoes % Gap

Molly (1999)

Summary: A bachelor becomes the unwilling guardian of his autistic, intellectually disabled sister; then an experimental treatment works a dramatic change in her brain and his attitude.

Release Date: October 29, 1999

Genres: Comedy, Drama, Romance

Director: John Duigan

Writer: Richard Christie

Runtime: 1 h 42 min

MPAA: PG-13

Production: Absolute Entertainment (II), Cockamamie, Heckerling-Caplan, Metro-Goldwyn-Mayer (MGM)

Distributor: Metro-Goldwyn-Mayer (MGM)

Country: United States

Language: English

Movie budget: $ 21,000,000

Domestic: $ 17,650

39 - Rotten Tomatoes % Gap

Grey Owl (1999)

Summary: The story of the life and work of the Canadian fur trapper-turned-conservationist who claimed to be an aboriginal North American.

Release Date: October 01, 1999

Genres: Drama, Biography, Western

Director: Richard Attenborough

Writer: William Nicholson

Runtime: 1 h 57 min

MPAA: PG-13

Production: Beaver Productions, Ajawaan Productions, Canadian Film or Video Production Tax Credit (CPTC), Largo Entertainment, Mel's Cite du Cinema, Transfilm

Distributor: Columbia TriStar Home Video, Hallmark Channel, Lionsgate, New City Releasing, YouTube

Countries: United Kingdom, Canada

Language: English

Movie budget: $ 30,000,000

Domestic: $ 632,617

38 - Rotten Tomatoes % Gap

Simply Irresistible (1999)

Summary: A magical crab works wonders for a terrible chef's culinary skills, leading her towards the man of her dreams.

Release Date: May 01, 2023

Genres: Comedy, Drama, Fantasy

Director: Mark Tarlov

Writer: Judith Roberts

Runtime: 1 h 36 min

MPAA: PG

Production: New Regency Productions, Polar Entertainment Corporation, Taurus Film

Distributor: Twentieth Century Fox

Countries: Germany, United States

Language: English

Movie budget: $ 6,000,000

Domestic: $ 4,398,989

36 - Rotten Tomatoes % Gap

In Too Deep (1999)

Summary: Right out of police academy, Jeff/Omar Epps starts as undercover cop in Cincinnati. First it's small time cases but he proves himself and moves up to a big case - befriending a brutal crime boss.

Release Date: August 25, 1999

Genres: Drama, Crime, Thriller

Director: Michael Rymer