Top 20 Fan-Favorite Movies of 1999: A Nostalgic Cinematic Journey

Ah, 1999! A year when Y2K was the biggest worry, Britney Spears was the newest pop sensation, and Furbies were the must-have toy. But let’s not forget, it was also a golden year for cinema. From mind-bending sci-fi to heart-wrenching drama, 1999 gifted us with a cinematic smorgasbord that still resonates today. So, grab your popcorn, dim the lights, and prepare to journey back in time as we revisit the top 20 fan-favorite movies of 1999. Whether you’re a film buff, a nostalgia junkie, or just looking for a good flick to watch, this list is your ticket to a celluloid time machine. So, buckle up and get ready to be transported back to the last year of the 20th century, where the silver screen was nothing short of spectacular. Let the countdown begin!
The Green Mile

The Green Mile

Release Date: 1999-12-10

Genres: Fantasy, Drama, Crime

“The Green Mile” is a captivating supernatural film set in a Southern prison during 1999. Starring Tom Hanks, Michael Clarke Duncan, and a talented ensemble cast, the story revolves around a gentle giant named John Coffey, who possesses an extraordinary power to heal people. As the head guard, Paul Edgecomb, discovers Coffey’s miraculous gift, he becomes determined to save him from his impending execution. Released on December 10, 1999, this movie is a must-watch for its gripping storyline and exceptional performances.

Cast: Tom Hanks (Paul Edgecomb) , Michael Clarke Duncan (John Coffey) , David Morse (Brutus “Brutal” Howell) , Bonnie Hunt (Jan Edgecomb) , Michael Jeter (Eduard Delacroix) , Doug Hutchison (Percy Wetmore) , Sam Rockwell (‘Wild Bill’ Wharton) , James Cromwell (Warden Hal Moores) , Barry Pepper (Dean Stanton) , Graham Greene (Arlen Bitterbuck) , Jeffrey DeMunn (Harry Terwilliger) , Patricia Clarkson (Melinda Moores) , Harry Dean Stanton (Toot-Toot) , Dabbs Greer (Old Paul Edgecomb) , Eve Brent (Elaine Connelly) , William Sadler (Klaus Detterick) , Mack Miles (Orderly Hector) , Rai Tasco (Man in Nursing Home) , Paula Malcomson (Marjorie Detterick) , Christopher Joel Ives (Howie Detterick) , Evanne Drucker (Kathe Detterick) , Bailey Drucker (Cora Detterick) , Brian Libby (Sheriff McGee) , Brent Briscoe (Bill Dodge) , Bill McKinney (Jack Van Hay)

Directors: Frank Darabont

Writers: Stephen King, Frank Darabont

Tags: southern usa, mentally disabled, based on novel or book, death row, jail guard, great depression, supernatural, psychopath, prison guard, jail, electric chair, torture, magic realism, healing, 1930s, abuse of power

Fight Club

Fight Club

Release Date: 1999-10-15

Genres: Drama

“Fight Club” is a gripping 1999 movie that explores the unconventional world of underground fight clubs. Starring Edward Norton, Brad Pitt, and Helena Bonham Carter, it follows the story of an insomniac and a soap salesman who find an outlet for their pent-up aggression through these secret clubs. As their concept gains popularity, chaos ensues, leading to a thrilling and unpredictable spiral towards destruction.

Cast: Edward Norton (The Narrator) , Brad Pitt (Tyler Durden) , Helena Bonham Carter (Marla Singer) , Meat Loaf (Robert “Bob” Paulson) , Jared Leto (Angel Face) , Zach Grenier (Richard Chesler) , Holt McCallany (The Mechanic) , Eion Bailey (Ricky) , Richmond Arquette (Intern) , David Andrews (Thomas) , Christina Cabot (Group Leader) , Tim DeZarn (Inspector Bird) , Ezra Buzzington (Inspector Dent) , Bob Stephenson (Airport Security Officer) , David Lee Smith (Walter) , Carl Ciarfalio (Lou’s Body Guard) , Stuart Blumberg (Car Salesman) , Mark Fite (Second Man at Auto Shop) , Matt Winston (Seminary Student) , Lauren Sánchez (Channel 4 Reporter) , Thom Gossom Jr. (Detective Stern) , Markus Redmond (Detective Kevin) , Van Quattro (Detective Andrew) , Michael Girardin (Detective Walker) , David Jean Thomas (Policeman)

Directors: David Fincher

Writers: Chuck Palahniuk, Jim Uhls

Tags: based on novel or book, support group, dual identity, nihilism, fight, rage and hate, insomnia, dystopia, alter ego, breaking the fourth wall, cult film, split personality, quitting a job, dissociative identity disorder, self destructiveness

The Matrix

The Matrix

Release Date: 1999-03-30

Genres: Action, Science Fiction

“The Matrix” is a mind-bending sci-fi flick released in 1999. Set in the future, it follows a computer hacker who teams up with a rebel group fighting against powerful computers that have taken over the world. Starring Keanu Reeves, Laurence Fishburne, and Carrie-Anne Moss, this action-packed film will keep you on the edge of your seat with its thrilling storyline and impressive visual effects.

Cast: Keanu Reeves (Thomas A. Anderson / Neo) , Laurence Fishburne (Morpheus) , Carrie-Anne Moss (Trinity) , Hugo Weaving (Agent Smith) , Joe Pantoliano (Cypher) , Marcus Chong (Tank) , Anthony Ray Parker (Dozer) , Matt Doran (Mouse) , Gloria Foster (Oracle) , Belinda McClory (Switch) , Paul Goddard (Agent Brown) , Robert Taylor (Agent Jones) , Ada Nicodemou (DuJour) , Julian Arahanga (Apoc) , David Aston (Rhineheart) , Marc Aden Gray (Choi) , Deni Gordon (Priestess) , Rowan Witt (Spoon Boy) , Eleanor Witt (Potential) , Janaya Pender (Potential) , Adryn White (Potential) , Natalie Tjen (Potential) , Bill Young (Lieutenant) , David O’Connor (FedEx Man) , Jeremy Ball (Businessman)

Directors: Lilly Wachowski, Lana Wachowski

Writers: Lilly Wachowski, Lana Wachowski

Tags: saving the world, artificial intelligence, man vs machine, philosophy, prophecy, martial arts, self sacrifice, dream, fight, hacker, insurgence, simulated reality , virtual reality, dystopia, truth, cyberpunk, dream world, woman director, messiah, action hero, gnosticism

American Beauty

American Beauty

Release Date: 1999-09-15

Genres: Drama

“American Beauty” is a captivating drama released in 1999 that tells the story of Lester Burnham, a suburban father going through a mid-life crisis. After becoming infatuated with his daughter’s attractive friend, Lester decides to make a change in his life. Starring Kevin Spacey, Annette Bening, and a talented ensemble cast, this movie explores themes of self-discovery and the pursuit of happiness.

Cast: Kevin Spacey (Lester Burnham) , Annette Bening (Carolyn Burnham) , Thora Birch (Jane Burnham) , Wes Bentley (Ricky Fitts) , Mena Suvari (Angela Hayes) , Chris Cooper (Colonel Frank Fitts) , Allison Janney (Barbara Fitts) , Peter Gallagher (Buddy Kane) , Scott Bakula (Jim Olmeyer) , Sam Robards (Jim Berkley) , Barry Del Sherman (Brad Dupree) , John Cho (Sale House Man #1) , Hal Fort Atkinson (Sale House Man #2) , Kent Faulcon (Sale House Man #3) , Ara Celi (Sale House Woman #1) , Sue Casey (Sale House Woman #2) , Brenda Wehle (Sale House Woman #3) , Lisa Cloud (Sale House Woman #4) , Amber Smith (Christy Kane) , Joel McCrary (Catering Boss) , Marissa Jaret Winokur (Janine) , Dennis Anderson (Mr. Smiley’s Manager) , Matthew Kimbrough (Firing Range Attendant) , Erin Cathryn Strubbe (Young Jane) , Alison Faulk (Spartanette #1)

Directors: Sam Mendes

Writers: Alan Ball

Tags: adultery, parent child relationship, midlife crisis, coming out, first time, virgin, estate agent, cheerleader, rose, satire, loneliness, dysfunctional family, dysfunctional marriage, dark comedy, suburbia, coming of age, marijuana, love affair, exercise, extramarital affair, quitting a job, retired army man, closeted homosexual, gay theme, teenager

The Sixth Sense

The Sixth Sense

Release Date: 1999-08-06

Genres: Mystery, Thriller, Drama

“The Sixth Sense” is a gripping psychological thriller released in 1999. It follows the story of child psychologist Malcolm Crowe, played by Bruce Willis, who forms a unique bond with a mysterious nine-year-old boy named Cole Sear, portrayed by Haley Joel Osment. As they navigate through an unexpected tragedy, Cole’s dark secret unravels, keeping you on the edge of your seat until the very end.

Cast: Bruce Willis (Malcolm Crowe) , Haley Joel Osment (Cole Sear) , Toni Collette (Lynn Sear) , Olivia Williams (Anna Crowe) , Trevor Morgan (Tommy Tammisimo) , Donnie Wahlberg (Vincent Grey) , Peter Anthony Tambakis (Darren) , Jeffrey Zubernis (Bobby) , Bruce Norris (Stanley Cunningham) , Glenn Fitzgerald (Sean) , Greg Wood (Mr. Collins) , Mischa Barton (Kyra Collins) , Angelica Page (Mrs. Collins) , Lisa Summerour (Bridesmaid) , Firdous Bamji (Young Man Buying Ring) , Samia Shoaib (Young Woman Buying Ring) , Hayden Saunier (Darren’s Mom) , Janis Dardaris (Kitchen Woman) , Neill Hartley (Visitor #2) , Sarah Ripard (Visitor #3) , Heidi Fischer (Visitor #4) , KaDee Strickland (Visitor #5) , Michael J. Lyons (Visitor #6) , Samantha Fitzpatrick (Kyra’s Sister) , Holly Cross Vagley (Society Lady #1)

Directors: M. Night Shyamalan

Writers: M. Night Shyamalan

Tags: philadelphia, pennsylvania, child abuse, loss of loved one, sense of guilt, confidence, psychology, dying and death, marriage crisis, afterlife, single, paranormal phenomena, psychological thriller, cowardliness, single mother, school play, ghost, child, spiritism, ghost child

Magnolia

Magnolia

Release Date: 1999-12-10

Genres: Drama

“Magnolia” is a captivating and emotionally charged film that takes place in the vibrant backdrop of San Fernando Valley. Released in 1999, this critically acclaimed movie weaves together the stories of various characters, portrayed by a talented ensemble including Philip Baker Hall, Tom Cruise, Julianne Moore, and more. With its grand scale and exploration of themes like happiness, forgiveness, and the search for meaning, “Magnolia” emerges as one of the best movies of 1999, leaving a lasting impact on its viewers.

Cast: Philip Baker Hall (Jimmy Gator) , Jeremy Blackman (Stanley Spector) , Tom Cruise (Frank ‘T.J.’ Mackey) , Philip Seymour Hoffman (Phil Parma) , William H. Macy (Quiz Kid Donnie Smith) , Julianne Moore (Linda Partridge) , John C. Reilly (Officer Jim Kurring) , Jason Robards (Earl Partridge) , Melora Walters (Claudia Wilson Gator) , Melinda Dillon (Rose Gator) , Michael Bowen (Rick Spector) , April Grace (Gwenovier) , Henry Gibson (Thurston Howell) , Alfred Molina (Solomon Solomon) , Ricky Jay (Burt Ramsey / Narrator) , Luis Guzmán (Luis) , Patrick Warren (Todd Geronimo) , Patricia Forte (Mim) , Cleo King (Marcie) , Eileen Ryan (Mary) , Pat Healy (Sir Edmund William Godfrey / Young Pharmacy Kid) , Paul F. Tompkins (Chad (voice)) , Miguel Pérez (Avi Solomon) , Patton Oswalt (Delmer Darion) , Craig Kvinsland (Brad the Bartender)

Directors: Paul Thomas Anderson

Writers: Paul Thomas Anderson

Tags: farewell, loss of loved one, regret, parent child relationship, suicide attempt, becoming an adult, dying and death, chance, child prodigy, daughter, unsociability, reconciliation, san fernando valley, multiple storylines, frog

The Straight Story

The Straight Story

Release Date: 1999-10-15

Genres: Drama

“The Straight Story” is a heartwarming and inspiring movie released in 1999. It tells the story of Alvin Straight, a retired farmer in his 70s, who embarks on a remarkable journey to reconcile with his ailing brother in Wisconsin. With no car or driver’s license, Alvin decides to travel on his old lawnmower, leading to a picturesque and deeply spiritual adventure. Starring Richard Farnsworth and Sissy Spacek, this film is a must-watch for its touching storyline and exceptional performances.

Cast: Richard Farnsworth (Alvin Straight) , Sissy Spacek (Rose Straight) , Harry Dean Stanton (Lyle Straight) , Everett McGill (Tom) , Kevin Farley (Harald Olsen) , John Farley (Thorvald Olsen) , Jane Galloway Heitz (Dorothy) , Joseph A. Carpenter (Bud) , Donald Wiegert (Sig) , Tracey Maloney (Nurse) , Dan Flannery (Doctor Gibbons) , Ed Grennan (Pete) , Jack Walsh (Apple) , Gil Pearson (Sun Ray Tours Bus Driver) , Barbara June Patterson (Woman on Bus) , James Cada (Danny Riordan, Clermont Resident) , Sally Wingert (Darla Riordan, Clermont Resident) , Barbara Kingsley (Janet Johnson, Clermont Resident) , Jim Haun (Johnny Johnson, Clermont Resident) , Leroy Swadley (Bar Patron) , Ralph Feldhacker (Farmer on Tractor) , Anastasia Webb (Crystal) , John Lordan (Priest) , Matt Guidry (Steve) , Wiley Harker (Verlyn Heller)

Directors: David Lynch

Writers: John Roach, Mary Sweeney

Tags: sibling relationship, mississippi river, wisconsin, lawnmower, iowa, biography, road trip, based on true story, family relationships, family, elderly man

All About My Mother

All About My Mother

Release Date: 1999-04-16

Genres: Comedy, Drama

“All About My Mother” is a heartfelt movie released in 1999 that tells the story of Manuela, a grieving mother who embarks on a journey to find her son’s father. Along the way, she forms unexpected connections with a transgender sex worker, a troubled actress, and a pregnant nun who is HIV-positive. With a talented cast including Cecilia Roth, Marisa Paredes, and Penélope Cruz, this film explores themes of love, loss, and the power of human connection.

Cast: Cecilia Roth (Manuela) , Marisa Paredes (Huma) , Candela Peña (Nina) , Antonia San Juan (Agrado) , Penélope Cruz (Rosa) , Rosa María Sardà (Rosa’s Mother) , Fernando Fernán Gómez (Rosa’s Father) , Fernando Guillén (Actor “Doctor”) , Toni Cantó (Lola) , Eloy Azorín (Esteban) , Carlos Lozano (Mario) , Manuel Morón (Doctor 1) , José Luis Torrijo (Doctor 2) , Juan José Otegui (Gynecologist) , Carmen Balagué () , Malena Gutiérrez (Malena) , Yael Barnatán (Yael) , Carme Fortuny (Carmen) , Patxi Freytez (Pharmacist) , Juan Marquez () , Michel Ruben (Alex) , Daniel Lanchas () , Rosa Manaut () , Carlos García Cambero (Heart Recipient) , Agustín Almodóvar (Taxi Driver)

Directors: Pedro Almodóvar

Writers: Pedro Almodóvar

Tags: barcelona, spain, transvestism, transsexuality, drug abuse, transplantation, madrid, spain, birthday, autograph, friends, lgbt

10 Things I Hate About You

10 Things I Hate About You

Release Date: 1999-03-30

Genres: Comedy, Romance, Drama

“Remember that classic teen movie from 1999, ’10 Things I Hate About You’? It’s about this guy named Cameron who instantly falls for Bianca, the most beautiful girl in his new school. But here’s the catch – Bianca can’t date until her older sister, Kat, goes out too. So, Cameron hatches a plan to set Kat up with a mysterious bad boy, and let’s just say, things get pretty interesting. With a star-studded cast including Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt, this movie is a must-watch for any fan of 90s teen flicks!”

Cast: Heath Ledger (Patrick Verona) , Julia Stiles (Katarina Stratford) , Joseph Gordon-Levitt (Cameron James) , Larisa Oleynik (Bianca Stratford) , David Krumholtz (Michael Eckman) , Andrew Keegan (Joey Donner) , Susan May Pratt (Mandella) , Gabrielle Union (Chastity) , Larry Miller (Walter Stratford) , Daryl Mitchell (Mr. Morgan) , Allison Janney (Ms. Perky) , David Leisure (Mr. Chapin) , Greg Jackson (Scruvy) , Kyle Cease (Bogey Lowenstien) , Terence Heuston (Derek) , Cameron Fraser (Trevor) , Eric Riedmann (Audio Visual Guy) , Quinn Maixner (Beautiful Jock) , Demegio Kimbrough (Coffee Kid) , Todd Butler (Coffee Kid) , Dennis Mosley (Cohort) , Bianca Kajlich (Coffee Girl) , Nick Vukelic (Drugged Out Loser) , Ben Laurance (Wimpy Loser) , Aidan Kennedy (Laughing Loser)

Directors: Gil Junger

Writers: Karen McCullah, Kirsten Smith

Tags: high school, deception, based on play or musical, coming of age, teen movie, shrew, valentine’s day, shakespeare in modern dress, opposites attract, duringcreditsstinger, teenage romance, overprotective father

Girl, Interrupted

Girl, Interrupted

Release Date: 1999-12-21

Genres: Drama

“Girl, Interrupted” is a captivating movie set in the late 1960s, following the journey of Susanna Kaysen. After a brief encounter with a psychiatrist, she finds herself on an unexpected adventure through a surreal world, questioning the boundaries between sanity and madness. With an incredible cast including Winona Ryder, Angelina Jolie, and Brittany Murphy, this thought-provoking film explores the challenges of choosing between conformity and the harsh realities of the outside world. Released on December 21, 1999, it’s definitely one of the best movies of that year.

Cast: Winona Ryder (Susanna Kaysen) , Angelina Jolie (Lisa Rowe) , Brittany Murphy (Daisy Randone) , Clea DuVall (Georgina Tuskin) , Elisabeth Moss (Polly Clark) , Whoopi Goldberg (Valerie Owens) , Vanessa Redgrave (Dr. Wick) , Jared Leto (Toby) , Jeffrey Tambor (Dr. Melvin Potts) , Travis Fine (Nurse John) , Angela Bettis (Janet Webber) , Jillian Armenante (Cynthia Crowley) , Drucie McDaniel (M.G.) , Christina Myers (Nurse Margie) , Mary Kay Place (Barbara Gilcrest) , KaDee Strickland (Bonnie Gilcrest) , Misha Collins (Tony) , Kurtwood Smith (Dr. Crumble) , David Scott Taylor (Cabby Monty Hoover) , Joanna Kerns (Annette) , Janet Greer (ER Nurse) , Anne Lewis (Dance Therapist) , Katie Rimmer (Tiffany)

Directors: James Mangold

Writers: James Mangold, Susanna Kaysen, Lisa Loomer, Anna Hamilton Phelan

Tags: based on novel or book, suicide attempt, identity, puberty, female friendship, biography, insanity, borderline personality disorder, based on true story, psychiatric hospital, escape, female protagonist, mental institution, based on memoir or autobiography, psychiatrist, hanging, mental illness, psychiatric ward, self mutilation, 1960s

Eyes Wide Shut

Eyes Wide Shut

Release Date: 1999-07-16

Genres: Drama, Thriller, Mystery

“Eyes Wide Shut” is a captivating movie from 1999 starring Tom Cruise and Nicole Kidman. It follows the story of Dr. Bill Harford, who becomes obsessed with exploring his own sexual desires after his wife confesses her fantasies. As he delves into an underground sexual group, Bill quickly realizes that he has gotten himself into a situation that he may not be able to handle.

Cast: Tom Cruise (Dr. William Harford) , Nicole Kidman (Alice Harford) , Sydney Pollack (Victor Ziegler) , Marie Richardson (Marion Nathanson) , Rade Šerbedžija (Milich) , Todd Field (Nick Nightingale) , Vinessa Shaw (Domino) , Alan Cumming (Desk Clerk) , Sky du Mont (Sandor Szavost) , Fay Masterson (Sally) , Leelee Sobieski (Milich’s Daughter) , Thomas Gibson (Carl) , Madison Eginton (Helena Harford) , Jackie Sawiris (Roz) , Leslie Lowe (Illona) , Peter Hans Benson (Bandleader) , Michael Doven (Ziegler’s Secretary) , Louise J. Taylor (Gayle) , Stewart Thorndike (Nuala) , Randall Paul (Harris) , Julienne Davis (Mandy) , Lisa Leone (Lisa) , Kevin Connealy (Lou Nathanson) , Mariana Hewett (Rosa) , Dan Rollman (Rowdy College Kid)

Directors: Stanley Kubrick

Writers: Stanley Kubrick, Arthur Schnitzler, Frederic Raphael

Tags: new york city, sexual obsession, prostitute, based on novel or book, christmas party, eroticism, orgy, masked ball, sacrifice, secret society, cult, conspiracy, marijuana, mansion, lust, drugs, disguise, illegal prostitution, cult film, sexual desire, voyeurism, erotic thriller, sex party, marital crisis, relationships, costume shop, hooker

The Insider

The Insider

Release Date: 1999-10-28

Genres: Drama, Thriller

“The Insider” is a gripping drama released in 1999 that tells the story of a research chemist who faces intense personal and professional attacks after deciding to expose the secrets of the tobacco industry on the popular TV show, 60 Minutes. Starring Al Pacino, Russell Crowe, and Christopher Plummer, this thought-provoking film sheds light on the challenges faced by whistleblowers and the power of standing up for the truth. It’s definitely a must-watch from the best voted movies of 1999!

Cast: Al Pacino (Lowell Bergman) , Russell Crowe (Jeffrey Wigand) , Christopher Plummer (Mike Wallace) , Diane Venora (Liane Wigand) , Philip Baker Hall (Don Hewitt) , Lindsay Crouse (Sharon Tiller) , Debi Mazar (Debbie De Luca) , Stephen Tobolowsky (Eric Kluster) , Colm Feore (Richard Scruggs) , Bruce McGill (Ron Motley) , Gina Gershon (Helen Caperelli) , Michael Gambon (Thomas Sandefur) , Rip Torn (John Scanlon) , Lynne Thigpen (Mrs. Williams) , Hallie Eisenberg (Barbara Wigand) , Michael Paul Chan (Norman the Cameraman) , Linda Hart (Mrs. Wigand) , Robert Harper (Mark Stern) , Nestor Serrano (FBI Agent Robertson) , Pete Hamill (NY Times Reporter) , Wings Hauser (Tobacco Lawyer) , Cliff Curtis (Sheikh Fadlallah) , Renee Olstead (Deborah Wigand) , Michael Moore (Michael Moore) , Gary Sandy (Sandefur’s Lawyer)

Directors: Michael Mann

Writers: Eric Roth, Michael Mann, Marie Brenner

Tags: spy, journalism, newspaper, research, interview, politics, tobacco, insider, conspiracy theory, reporter, whistleblower, tobacco industry, legal drama, legal thriller

Boys Don't Cry

Boys Don’t Cry

Release Date: 1999-09-02

Genres: Crime, Drama

“Boys Don’t Cry” is a powerful and thought-provoking movie released in 1999. It tells the story of a young transgender man living in rural Nebraska, as he navigates his gender identity and searches for love. With a talented cast including Hilary Swank, Chloë Sevigny, and Peter Sarsgaard, this film explores important themes and leaves a lasting impact on its viewers.

Cast: Hilary Swank (Brandon Teena) , Chloë Sevigny (Lana Tisdel) , Peter Sarsgaard (John Lotter) , Brendan Sexton III (Tom Nissen) , Alicia Goranson (Candace) , Alison Folland (Kate) , Jeannetta Arnette (Lana’s Mom) , Rob Campbell (Brian) , Matt McGrath (Lonny) , Cheyenne Rushing (Nicole) , Robert Prentiss (Trucker) , Josh Ridgway (Kwik Stop Cashier) , Craig Erickson (Trucker in Kwik Stop) , Stephanie Sechrist (April) , Jerry Haynes (Judge) , Lou Perryman (Sheriff) , Lisa Renee Wilson (Pam) , Jackson D. Kane (Sam Phillips) , Joseph Gibson (Tom) , Michael Tripp (Nerdy Teen) , Shana McClendon (Girl in Car) , Libby Villari (Nurse) , Paige Carl Griggs (Dave (Deputy)) , Gail Cronauer (Clerk) , Guilford Adams (Brandon’s Father (uncredited))

Directors: Kimberly Peirce

Writers: Kimberly Peirce, Andy Bienen

Tags: rape, identity, small town, based on true story, love, friends, murder, romance, cross dressing, anger, hate crime, woman director, nebraska, trans man, small town murder, transphobia, gender identity, 1990s, rural town

The Hurricane

The Hurricane

Release Date: 1999-09-17

Genres: Drama

“The Hurricane” is a gripping 1999 movie based on the true story of Rubin “Hurricane” Carter, a boxer who was wrongly convicted of murder. Starring Denzel Washington and a talented ensemble cast, the film follows Carter’s fight for justice and the unwavering support he receives from those who believe in his innocence. Released on September 17, 1999, this powerful drama is definitely one of the best movies of that year.

Cast: Denzel Washington (Rubin “Hurricane” Carter) , Vicellous Reon Shannon (Lesra Martin) , Deborah Kara Unger (Lisa Peters) , Liev Schreiber (Sam Chaiton) , John Hannah (Terry) , Dan Hedaya (Della Pesca) , Debbi Morgan (Mae Thelma) , Clancy Brown (Lt. Jimmy Williams) , David Paymer (Myron Bedlock) , Harris Yulin (Leon Friedman) , Rod Steiger (Judge Sarokin) , Badja Djola (Mobutu) , Vincent Pastore (Alfred Bello) , Al Waxman (Warden) , David Lansbury (U.S. Court Prosecutor) , Garland Whitt (John Artis) , Chuck Cooper (Earl Martin) , Brenda Denmark (Alma Martin) , Marcia Bennett (Jean Wahl) , Beatrice Winde (Louise Cockersham) , Mitchell Taylor Jr. (Young Rubin Carter) , Bill Raymond (Paterson Judge) , Merwin Goldsmith (Judge Larner) , John A. MacKay (Man at Falls) , Donnique Privott (Boy at the Falls)

Directors: Norman Jewison

Writers: Armyan Bernstein, Dan Gordon, Rubin ‘Hurricane’ Carter

Tags: prison, new jersey, 1970s, boxer, boxing school, biography, based on memoir or autobiography, 1960s, boxing, legal drama, legal thriller

Being John Malkovich

Being John Malkovich

Release Date: 1999-10-29

Genres: Comedy, Drama, Fantasy

“Hey, I just found this awesome movie from 1999 called ‘Being John Malkovich’! It’s about a puppeteer named Craig who discovers a mysterious portal that leads directly into the mind of the famous actor, John Malkovich. Once inside, things get crazy as people become obsessed with taking over Malkovich’s body. It’s a mind-bending and hilarious ride with a star-studded cast including John Cusack, Cameron Diaz, and Catherine Keener. You should definitely check it out!”

Cast: John Cusack (Craig Schwartz) , John Malkovich (John Horatio Malkovich) , Cameron Diaz (Lotte Schwartz) , Catherine Keener (Maxine Lund) , Mary Kay Place (Floris) , Orson Bean (Dr. Lester) , Charlie Sheen (Charlie) , Reggie Hayes (Don) , W. Earl Brown (First J.M. Inc. Customer) , Carlos Jacott (Larry the Agent) , Willie Garson (Guy in Restaurant) , K.K. Dodds (Wendy) , Byrne Piven (Captain Mertin) , Judith Wetzell (Tiny Woman) , Gregory Sporleder (Drunk at Bar) , Octavia Spencer (Woman in Elevator) , Ned Bellamy (Derek Mantini) , Eric Weinstein (Father at Puppet Show) , Madison Lanc (Daughter at Puppet Show) , Kevin Carroll (Cab Driver) , Gerald Emerick (Sad Man in Line) , Richard Fancy (Johnson Heyward) , Patti Tippo (Malkovich’s Mother) , Daniel Hansen (Boy Malkovich) , Mariah O’Brien (Girl Creeped Out by Malkovich)

Directors: Spike Jonze

Writers: Charlie Kaufman

Tags: individual, transvestism, sexual identity, witch, identity, subconsciousness, new identity, pet, chimp, puppeteer, appropriation of another human being, externally controlled action, pet shop, secret love, actor playing themself

Office Space

Office Space

Release Date: 1999-02-19

Genres: Comedy

“Office Space” is a hilarious comedy released in 1999 that follows the story of a disillusioned white-collar worker who undergoes hypnotherapy. However, instead of finding relief, he enters a carefree state of mind that leads him to rebel against his monotonous job and attempt a comically disastrous embezzlement scheme. Starring Ron Livingston, Jennifer Aniston, and a talented ensemble cast, this film offers a relatable and entertaining take on the frustrations of corporate life.

Cast: Ron Livingston (Peter Gibbons) , Jennifer Aniston (Joanna) , David Herman (Michael Bolton) , Ajay Naidu (Samir Nagheenanajar) , Diedrich Bader (Lawrence) , Stephen Root (Milton Waddams) , Gary Cole (Bill Lumbergh) , Richard Riehle (Tom Smykowski) , Ali Wentworth (Anne) , Joe Bays (Dom Portwood) , John C. McGinley (Bob Slydell) , Paul Willson (Bob Porter) , Kinna McInroe (Nina) , Todd Duffey (Brian, Chotchkie’s Waiter) , Greg Pitts (Drew) , Michael McShane (Dr. Swanson) , Linda Wakeman (Laura Smykowski) , Jennifer Jane Emerson (Female Temp) , Kyle Scott Jackson (Rob Newhouse) , Orlando Jones (Steve – Magazine Salesman) , Barbara George-Reiss (Peggy – Lumbergh’s Secretary) , Tom Schuster (Construction Foreman) , Rupert Reyes (Mexican Waiter) , Jackie Belvin (Swanson’s Patient #1) , Gabriel Folse (Swanson’s Patient #2)

Directors: Mike Judge

Writers: Mike Judge

Tags: printer, work, dallas texas, bad boss, satire, suburbia, co-workers relationship, corporate world, downsizing, software engineer, burnout, stapler, duringcreditsstinger, business rivalry

Ghost Dog: The Way of the Samurai

Ghost Dog: The Way of the Samurai

Release Date: 1999-06-02

Genres: Crime, Drama

“Ghost Dog: The Way of the Samurai” is a captivating movie released in 1999 that tells the story of an African-American Mafia hitman who draws inspiration from ancient Japanese samurai. Starring Forest Whitaker and an impressive cast, the film follows the hitman as he becomes the target of the mob. With its unique blend of cultures and thrilling storyline, this movie is definitely worth checking out if you’re a fan of action and suspense.

Cast: Forest Whitaker (Ghost Dog) , John Tormey (Louie) , Isaach De Bankolé (Raymond) , Cliff Gorman (Sonny Valerio) , Henry Silva (Ray Vargo) , Tricia Vessey (Louise Vargo) , Victor Argo (Vinny) , Camille Winbush (Pearline) , Gene Ruffini (Old Consigliere) , Richard Portnow (Handsome Frank) , Frank Minucci (Big Angie) , Dennis Liu (Chinese Restaurant Owner) , Frank Adonis (Valerio’s Bodyguard) , Damon Whitaker (Young Ghost Dog) , Kenny Guay (Boy in Window) , Vince Viverito (Johnny Morini) , Gano Grills (Gangsta in Red) , Touché Cornel (Gangsta in Red) , Jamie Hector (Gangsta in Red) , Chuck Jeffreys (Mugger) , Yan Ming Shi (Kung Fu Master) , Joseph Rigano (Joe Rags) , Roberto Lopez (Punk in Alley) , Salvatore Alagna (Punk in Alley) , Jerry Todisco (Punk in Alley)

Directors: Jim Jarmusch

Writers: Jim Jarmusch

Tags: hip-hop, hitman, mission of murder, revenge, mafia, park, pigeon, hagakure, ice cream, haitian, cd player, arm sling, racial slur, carrier pigeon, ice cream truck, contract killer, code of the samurai

Man on the Moon

Man on the Moon

Release Date: 1999-12-22

Genres: Comedy, Drama

“Man on the Moon” is a captivating biographical film released in 1999 that delves into the life and career of the eccentric avant-garde comedian, Andy Kaufman. With an incredible cast including Jim Carrey, Danny DeVito, Courtney Love, and more, this movie takes you on a journey through Kaufman’s unique and unconventional world. Prepare to be entertained and fascinated by this intriguing portrayal of a comedic genius.

Cast: Jim Carrey (Andy Kaufman / Tony Clifton) , Danny DeVito (George Shapiro) , Courtney Love (Lynne Margulies) , Paul Giamatti (Bob Zmuda) , Vincent Schiavelli (Maynard Smith) , Peter Bonerz (Ed Weinberger) , Jerry Lawler (Himself) , Gerry Becker (Stanley Kaufman) , Leslie Lyles (Janice Kaufman) , Greyson Erik Pendry (Little Michael Kaufman) , Brittany Colonna (Baby Carol Kaufman) , Bobby Boriello (Little Andy Kaufman) , George Shapiro (Mr. Besserman) , Budd Friedman (Himself) , Tom Dreesen (Wiseass Comic) , Thomas Armbruster (Improv Piano Player) , Pamela Abdy (Diane Barnett) , Wendy Polland (Little Wendy) , Cash Oshman (Yogi) , Matt Price (Meditation Student) , Christina Cabot (Meditation Student) , Richard Belzer (Richard Belzer) , Melanie Vesey (Carol Kaufman) , Michael Kelly (Michael Kaufman) , Miles Chapin (SNL Assistant)

Directors: Miloš Forman

Writers: Scott Alexander, Larry Karaszewski

Tags: show business, comedian, biography, pro wrestling, mentally unstable, pro wrestlers

Notting Hill

Notting Hill

Release Date: 1999-05-21

Genres: Romance, Comedy

“Notting Hill” is a heartwarming romantic comedy released in 1999. It tells the story of William Thacker, a London bookstore owner, whose life takes an unexpected turn when he meets famous American actress Anna Scott. Their chance encounter leads to a whirlwind romance, as they navigate the challenges of their different lifestyles in the name of love. With a stellar cast including Julia Roberts and Hugh Grant, this movie is a delightful blend of humor, romance, and the magic of unexpected connections.

Cast: Julia Roberts (Anna Scott) , Hugh Grant (William Thacker) , Gina McKee (Bella) , Tim McInnerny (Max) , Rhys Ifans (Spike) , Emma Chambers (Honey) , Hugh Bonneville (Bernie) , Richard McCabe (Tony) , James Dreyfus (Martin) , Dylan Moran (Rufus the Thief) , Roger Frost (Annoying Customer) , Henry Goodman (Ritz Concierge) , Julian Rhind-Tutt (‘Time Out’ Journalist) , Lorelei King (Anna’s Publicist) , John Shrapnel (PR Chief) , Emily Mortimer (Perfect Girl) , Dorian Lough (Loud Man in Restaurant) , Sanjeev Bhaskar (Loud Man in Restaurant) , Paul Chahidi (Loud Man in Restaurant) , Matthew Whittle (Loud Man in Restaurant) , Mischa Barton (12-year-old Actress) , Clarke Peters (‘Helix’ Lead Actor) , Ann Beach (William’s Mother) , Samuel West (Anna’s Co-Star) , Tony Armatrading (Security Man)

Directors: Roger Michell

Writers: Richard Curtis, Emma Freud

Tags: london, england, england, bookshop, movie business, roommate, birthday, new love, paparazzi, press conference, wheelchair, bath tub, cohabitant, interview, friendship, fame, falling in love, celebration, group of friends, movie star, dinner party, famous actor

The Boondock Saints

The Boondock Saints

Release Date: 1999-01-22

Genres: Action, Thriller, Crime

“The Boondock Saints” is a thrilling action film released in 1999 that follows the story of Irish Catholic twin brothers, Conner and Murphy. Fueled by their faith, they take matters into their own hands to rid Boston of crime, becoming controversial heroes in the process. With an eccentric FBI agent hot on their trail, this movie promises an intense and blood-soaked journey, starring talented actors like Willem Dafoe, Sean Patrick Flanery, and Norman Reedus.

Cast: Willem Dafoe (Paul Smecker) , Sean Patrick Flanery (Conner MacManus) , Norman Reedus (Murphy MacManus) , David Della Rocco (Rocco) , Billy Connolly (II Duce) , David Ferry (Detective Dolly) , Brian Mahoney (Detective Duffy) , Bob Marley (Detective Greenly) , Richard Fitzpatrick (The Chief) , William Young (Monsignor) , Robert Pemberton (Macklepenny) , Bill Craig (McGerkin) , Dot-Marie Jones (Rozengurtle Baumgartener) , Scott Griffith (Ivan Checkov) , Layton Morrison (Vladdy) , James Binkley (Officer Newman) , Matthew Chaffee (Officer Chaffey) , Robert Vernon Eaton (Officer Langley) , Kym Kristalie (Beat-Up Woman) , Gerard Parkes (Doc) , Peter Windrem (Reporter #1) , Elizabeth Saunders (Reporter #2) , Jeffrey R. Smith (Bartender) , Jonathan Higgins (Officer Mitchell) , Anthony Chrysostom (Judge)

Directors: Troy Duffy

Writers: Troy Duffy

Tags: detective, boston, massachusetts, irish-american, bratva (russian mafia), shootout, prologue, police station, pager, mob boss, duringcreditsstinger, vigilantism, brother brother relationship, public execution

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