# List of LGBTQ-related films of 1999

This is a list of lesbian, gay, bisexual, transgender or queer-related films released in 1999. It contains theatrically released films that deal with important gay, lesbian, bisexual, transgender or queer characters or issues and may have same-sex romance or relationships as a plot device.

## Films

| Title | Director | Country | Genre | Cast | Notes |
| $30 | Gregory Cooke | United States | Short, comedy | Sara Gilbert, Erik MacArthur and Gregory Itzin | A father buys his closeted son a night with a prostitute |
| 24 Nights | Kieran Turner | United States | Comedy | Kevin Isola, Aida Turturro and Stephen Mailer | |
| After Stonewall | John Scagliotti | United States | Documentary | | |
| Aimée & Jaguar | Max Färberböck | Germany | Romance, war, drama | Juliane Köhler, Maria Schrader, Johanna Wokalek, Elisabeth Degen, Heike Makatsch and Detlev Buck | Based on the book by Erica Fischer chronicling the lives of Lilly Wust and Felice Schragenheim during World War II |
| All About My Mother | Pedro Almodóvar | Spain France | Drama | Cecilia Roth, Marisa Paredes, Antonia San Juan, Penélope Cruz and Candela Peña | |
| American Beauty | Sam Mendes | United States | Drama | Kevin Spacey, Annette Bening, Thora Birch, Chris Cooper | This film won the Academy Award for best picture. |
| Atomic Saké | Louise Archambault | Canada | Short drama | Audrey Benoit, Suzanne Clément, Noémie Godin-Vigneau | |
| The Attack of the Giant Moussaka | Panos H. Koutras | Greece | Comedy, sci-fi | Yannis Aggelakis, Myriam Vourou, Christos Mantakas. Gregory Patrikareas, Eugene Dimitriou and Themis Bazaka | |
| Beau travail | Claire Denis | France | Drama | Denis Lavant, Michel Subor and Grégoire Colin | Based on the novella Billy Budd by Herman Melville |
| Being John Malkovich | Spike Jonze | United States | Fantasy, comedy, drama | John Cusack, Cameron Diaz and Catherine Keener | John Malkovich and Charlie Sheen appear as themselves |
| Belle maman | Gabriel Aghion | France | Comedy | Catherine Deneuve, Line Renaud, Stéphane Audran | |
| Beloved/Friend (Amic/Amat) | Ventura Pons | Spain | Drama | Josep María Pou, Rosa Maria Sardà, Mario Gas, David Selvas and Irene Montalà | a.k.a. Beloved/Friend; based on the book Testament by Josep Maria Benet i Jornet |
| Below the Belt | Dominique Cardona, Laurie Colbert | Canada | Short drama | Nathalie Toriel, Cara Pifko, Tanja Jacobs | |
| Better Than Chocolate | Anne Wheeler | Canada | Romance, comedy | Wendy Crewson, Karyn Dwyer, Christina Cox, Ann-Marie MacDonald and Peter Outerbridge | |
| The Big Brass Ring | George Hickenlooper | United States | Drama | William Hurt, Nigel Hawthorne, Irene Jacob, Jefferson Mays and Miranda Richardson | The film's script was heavily rewritten by Hickenlooper and F. X. Feeney from a previous screenplay written in the early 1980s by Orson Welles and Oja Kodar |
| The Boondock Saints | Troy Duffy | United States | Crime, drama | Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco and Billy Connolly | |
| Boys Don't Cry | Kimberly Peirce | United States | Crime, drama | Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III and Alison Folland | Based on the real-life story of Brandon Teena |
| Burlesk King | Mel Chionglo | Philippines | Drama | Rodel Velayo, Leonardo Litton, Elizabeth Oropesa, Raymond Bagatsing and Cherry Pie Picache | 2nd part of a trilogy about strippers in Manila's gay bars |
| But I'm a Cheerleader | Jamie Babbit | United States | Comedy, drama | Natasha Lyonne, Clea DuVall, Melanie Lynskey, RuPaul, Eddie Cibrian, Wesley Mann and Richard Moll | |
| Chutney Popcorn | Nisha Ganatra | United States | Comedy, drama | Nisha Ganatra, Jill Hennessy, Sakina Jaffrey and Madhur Jaffrey | |
| Chill Out | Andreas Struck | Germany | Drama | Tatjana Blacher, Sebastian Blomberg and Werner Heinrichmöller | |
| Creature | Parris Patton | United States | Documentary | Stacey "Hollywood" Dean, Filberto Ascencio, Butch Dean, Dusty Dean | Documentary by Parris Patton about trans woman Stacey Hollywood; a four-year chronicle of Stacey's transformation into womanhood, life in the West Hollywood LGBT nightclub scene, and her journey from Los Angeles back home to visit her conservative Christian family in North Carolina. |
| Cruel Intentions | Roger Kumble | United States | Drama, thriller | Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon | Modern adaptation of the novel Les Liaisons dangereuses by Pierre Choderlos de Laclos |
| Deep Inside Clint Star | Clint Alberta | Canada | Documentary | | |
| Le derrière | Valérie Lemercier | France | Comedy | Valérie Lemercier, Claude Rich, Dieudonné, Marthe Keller and Patrick Catalifo | |
| An Early Frost | Pierre Pinaud | France | Short, drama | Amandine Sroussi, Serpentine Teyssier and Laurent Manzoni | a.k.a. Gelée précoce |
| The Einstein of Sex: Life and Work of Dr. M. Hirschfeld | Rosa von Praunheim | Germany Netherlands | History, drama | Friedel von Wangenheim, Ben Becker, Wolfgang Völz, Otto Sander and Meret Becker | |
| Election | Alexander Payne | United States | Comedy, drama | Matthew Broderick, Reese Witherspoon | Based on the novel by Tom Perrotta |
| External Affairs | Peter Moss | Canada | Drama | Victor Garber, Kenneth Welsh | TV movie |
| Fight Club | David Fincher | United States | Drama, thriller | Brad Pitt, Edward Norton, Helena Bonham Carter, Meat Loaf, and Jared Leto | Based on the novel of the same name by Chuck Palahniuk, it explores themes of homoeroticism. |
| The Five Senses | Jeremy Podeswa | Canada | Drama | Mary-Louise Parker, Gabrielle Rose, Molly Parker, Daniel MacIvor, Philippe Volter, Nadia Litz, Brendan Fletcher, Marco Leonardi, Pascale Bussières, Paul Soles, Richard Clarkin | |
| Flawless | Joel Schumacher | United States | Comedy, drama | Robert De Niro, Philip Seymour Hoffman, Barry Miller, Chris Bauer, Wilson Jermaine Heredia and Daphne Rubin-Vega | |
| Floating | William Roth | United States | Romance, drama | Norman Reedus, Chad Lowe, Will Lyman, Sybil Temchen and Casey Affleck | |
| Freeway II: Confessions of a Trickbaby | Matthew Bright | United States | Exploitation | Natasha Lyonne, Vincent Gallo, María Celedonio | |
| Friends & Lovers | George Haas | United States | Romance, drama | Stephen Baldwin, Danny Nucci, George Newbern, Alison Eastwood, Claudia Schiffer, Robert Downey Jr., Neill Barry, Suzanne Cryer | |
| Full Blast | Rodrigue Jean | Canada | Drama, musical | David La Haye, Martin Desgagné, Louise Portal, Marie-Jo Thério, Patrice Godin | Based on the novel L'Ennemi que je connais by Martin Pitre |
| Gendernauts - Eine Reise durch die Geschlechter | Monika Treut | Germany United States | Documentary | Sandy Stone, Texas Tomboy, Susan Stryker and Hida Viloria | a.k.a. Gendernauts: A Journey Through Shifting Identities |
| Go | Doug Liman | United States | Comedy, crime | William Fichtner, Katie Holmes, Jay Mohr, Sarah Polley, Scott Wolf and features Taye Diggs, Breckin Meyer, Timothy Olyphant, Desmond Askew, Jane Krakowski, J. E. Freeman, and Melissa McCarthy | |
| The Green Elephant | Svetlana Baskova | Russia | Horror | Sergey Pakhomov, Vladimir Epifantsev | |
| Happy, Texas | Mark Illsley | United States | Crime, comedy | Jeremy Northam, Steve Zahn, Ally Walker, Illeana Douglas and William H. Macy | |
| Hit and Runway | Christopher Livingston | United States | Comedy | Michael Parducci, Peter Jacobson and Judy Prescott | |
| I Know a Place | Roy Mitchell | Canada | Short documentary | Bob Goderre | |
| Je vois déjà le titre | Martial Fougeron | France | Short, drama | Denis D'Arcangelo, Orazio Massaro and Michèle Moretti | aka I already see the title |
| Just One Time | Lane Janger | United States | Comedy | Lane Janger, Joelle Carter, Guillermo Díaz and Jennifer Esposito | |
| Laugh in the Dark | Justine Pimlott | Canada | Documentary | Gary Colwell, Don Morden, Doris Mehegan | |
| Lola and Billy the Kid | Kutlug Ataman | Germany Turkey | Drama | Gandi Mukli, Baki Davrak, Erdal Yıldız [de], Murat Yılmaz, Inge Keller and Michael Gerber | Known in German as Lola und Bilidikid |
| Love in the Mirror (Amor nello specchio) | Salvatore Maira | Italy | Drama | Anna Galiena, Peter Stormare and Simona Cavallari | |
| L'un dans l'autre | Laurent Larivière | France | Short | Gérald Broclawik, François Revaclier and Isabelle Malin | aka In and Out |
| The Matrix | The Wachowskis | United States | Science-fiction, Action | Keanu Reeves, Laurence Fishburne, Hugo Weaving, Carrie-Anne Moss, and Joe Pantoliano | The film was confirmed by Lilly to be an allegory for transgender themes, with the Matrix being a transformation. One of the characters was intended to be male in the real world and female in the Matrix. |
| Memento Mori | Kim Tae-yong, Min Kyu-dong | South Korea | Horror, romance, drama | Lee Young-jin, Park Ye-jin, Kim Min-sun and Gong Hyo-jin | |
| My Gentleman Friends | Moze Mossanen | Canada | Docudrama | Aron Tager, David Gardner, François Klanfer, Christina Collins | |
| Oi! Warning | Benjamin Reding, Dominik Reding | Germany | Drama | Sascha Backhaus, Sascha Goerts, Sandra Borgmann and Jens Veith | |
| Piglets | Luc Feit, Marcus Sauermann | Germany | Short, comedy | Andreja Schneider, Christoph Marti and Tobias Bonn | aka Ferkel |
| The Pinco Triangle | Patrick Crowe, Tristan R. Whiston | Canada | Drama | Michael Fitzgerald, Lorraine Segato | |
| Rites of Passage | Victor Salva | United States | Drama, thriller | Dean Stockwell, James Remar, Robert Glen Keith and Jason Behr | |
| Second Skin | Gerardo Vera | Spain | Romance, drama | Javier Bardem, Jordi Molla, Ariadna Gil, Cecilia Roth and Mercedes Sampietro | |
| See You in Hell, My Darling | Nikos Nikolaidis | Greece | Drama | Vicky Harris, Valeria Christodoulidou, Paschalis Tsarouhas, Nikos Kordinos and Panos Vourlamis | |
| Set Me Free (Emporte-moi) | Léa Pool | Switzerland Canada France | Drama | Karine Vanasse, Pascale Bussières, Miki Manojlovic and Alexandre Mérineau | |
| The Sex Monster | Mike Binder | United States | Comedy | Mariel Hemingway, Mike Binder, Renee Humphrey (credited as Renée Humphrey) | |
| Skin Gang | Bruce La Bruce | Canada Germany United Kingdom Japan | Drama, adult | Steve Masters, Eden Miller, Slava Mogutin, Ralph Steel and Daniel Bätscher | a.k.a. Skin Flick |
| Sleeping Beauties | Jamie Babbit | United States | Short | Sarah Lassez, Radha Mitchell, Clea DuVall, Vince Vieluf and Rose McGowan | |
| Speedway Junky | Nickolas Perry | United States | Drama | Jesse Bradford, Jordan Brower, Jonathan Taylor Thomas, Daryl Hannah, Tiffani Thiessen and Patsy Kensit | |
| Taboo | Nagisa Oshima | France United Kingdom Japan | Drama | Takeshi Kitano, Ryuhei Matsuda. Shinji Takeda and Tadanobu Asano | a.k.a. Gohatto |
| The Talented Mr. Ripley | Anthony Minghella | United States | Crime, drama, thriller | Jude Law, Matt Damon, Gwyneth Paltrow, Cate Blanchett, Philip Seymour Hoffman, Jack Davenport | Based on the novel of the same name by Patricia Highsmith |
| Three to Tango | Damon Santostefano | United States | Comedy, Romance | Matthew Perry, Neve Campbell, Dylan McDermott, Oliver Platt | |
| Trick | Jim Fall | United States | Comedy, romance, musical | Christian Campbell, John Paul Pitoc, Tori Spelling, Lorri Bagley, Brad Beyer, Steve Hayes and Clinton Leupp | |
| The Velocity of Gary | Dan Ireland | United States | Drama, comedy | Thomas Jane, Salma Hayek, Vincent D'Onofrio | a.k.a. The Velocity of Gary* *(Not His Real Name) |
| Where Lies the Homo? | Jean-François Monette | Canada | Documentary | | |
| Why Not Me? | Stéphane Giusti | Spain France Switzerland | Comedy | Amira Casar, Julie Gayet, Bruno Putzulu, Alexandra London, Carmen Chaplin, Johnny Hallyday, Marie-France Pisier, Brigitte Roüan, Assumpta Serna and Elli Medeiros | |