List of American films of 1999
A list of American films released in 1999.
American Beauty won the Academy Award for Best Picture.
| Title | Director | Cast | Genre | Notes |
| 10 Things I Hate About You | Gil Junger | Julia Stiles, Heath Ledger, Larisa Oleynik, Joseph Gordon-Levitt, David Krumholtz, Andrew Keegan, Gabrielle Union | Romantic comedy | |
| The 13th Warrior | John McTiernan | Antonio Banderas, Diane Venora, Vladimir Kulich, Dennis Storhøi, Omar Sharif, Clive Russell, Richard Bremmer | Action | |
| 200 Cigarettes | Risa Bramon Garcia | Ben Affleck, Casey Affleck, Dave Chappelle, Guillermo Diaz, Angela Featherstone, Janeane Garofalo, Gaby Hoffmann, Kate Hudson, Courtney Love, Jay Mohr, Martha Plimpton, Christina Ricci, Paul Rudd | Comedy, Drama | |
| The 4th Floor | Josh Klausner | Juliette Lewis, William Hurt, Shelley Duvall | Horror | |
| 8mm | Joel Schumacher | Nicolas Cage, Joaquin Phoenix, James Gandolfini, Peter Stormare, Catherine Keener, Anthony Heald | Thriller | |
| The Adventures of Elmo in Grouchland | Gary Halvorson | Kevin Clash, Mandy Patinkin, Vanessa L. Williams | Children's film | |
| American Beauty | Sam Mendes | Kevin Spacey, Annette Bening, Chris Cooper, Wes Bentley, Thora Birch, Mena Suvari, Allison Janney, Peter Gallagher | Drama | won 5 Oscars |
| American Movie | Chris Smith | Mark Borchardt, Tom Schimmels | Documentary | |
| American Pie | Paul Weitz, Chris Weitz | Jason Biggs, Seann William Scott, Tara Reid, Shannon Elizabeth, Chris Klein, Alyson Hannigan, Thomas Ian Nicholas, Mena Suvari, Natasha Lyonne, Eddie Kaye Thomas, Eugene Levy | Comedy | |
| Analyze This | Harold Ramis | Robert De Niro, Billy Crystal, Lisa Kudrow | Comedy | |
| Angel's Dance | David L. Corley | James Belushi, Sheryl Lee, Kyle Chandler | Action comedy | |
| Animal Farm | Joseph Stephenson | Kelsey Grammer, Ian Holm, Paul Scofield, Patrick Stewart, Julia Ormond, Peter Ustinov | Family, Animation | from George Orwell novel; made for TV |
| Anna and the King | Andy Tennant | Jodie Foster, Chow Yun-fat | Drama | based on Anna and the King of Siam |
| Annie | Rob Marshall | Alicia Morton, Victor Garber, Kathy Bates | Musical | Little Orphan Annie |
| Any Given Sunday | Oliver Stone | Al Pacino, Dennis Quaid, Cameron Diaz, Jamie Foxx, James Woods, LL Cool J, John C. McGinley, Ann-Margret | Drama, Sports | |
| Anywhere but Here | Wayne Wang | Susan Sarandon, Natalie Portman, Shawn Hatosy, Hart Bochner | Drama | |
| Arlington Road | Mark Pellington | Jeff Bridges, Tim Robbins, Joan Cusack, Hope Davis | Thriller | |
| The Astronaut's Wife | Rand Ravich | Johnny Depp, Charlize Theron, Joe Morton | Science fiction | |
| At First Sight | Irwin Winkler | Val Kilmer, Mira Sorvino, Kelly McGillis, Nathan Lane, Steven Weber | Romance | |
| Atomic Train | David Jackson, Dick Lowry | Rob Lowe, Kristin Davis, Esai Morales, John Finn | Action | |
| ' | Jay Roach | Mike Myers, Heather Graham, Robert Wagner, Seth Green, Michael York, Verne Troyer, Will Ferrell | Action Comedy | sequel to ' |
| Baby Geniuses | Bob Clark | Kathleen Turner, Christopher Lloyd, Peter MacNicol, Kim Cattrall, Ruby Dee, Dom DeLuise | Family | |
| The Bachelor | Gary Sinyor | Chris O'Donnell, Renée Zellweger, Edward Asner | Romantic comedy | |
| Bats | Louis Morneau | Lou Diamond Phillips, Dina Meyer | Horror | |
| Being John Malkovich | Spike Jonze | John Cusack, Cameron Diaz, Catherine Keener, John Malkovich | Comedy | |
| Bellyfruit | Kerri Green | Michael Peña | Drama | |
| Beowulf | Graham Baker | Christopher Lambert, Rhona Mitra | Fantasy | |
| Best Laid Plans | Mike Barker | Reese Witherspoon, Alessandro Nivola, Josh Brolin | Crime | |
| The Best Man | Malcolm D. Lee | Taye Diggs, Monica Calhoun, Morris Chestnut, Nia Long | Romantic comedy | |
| Beyond the Mat | Barry W. Blaustein | Mick Foley, Terry Funk, Jesse Ventura, The Rock | Documentary | |
| Bicentennial Man | Chris Columbus | Robin Williams, Sam Neill, Embeth Davidtz, Oliver Platt, Wendy Crewson, Hallie Kate Eisenberg | Science fiction | from Isaac Asimov novel |
| Big Daddy | Dennis Dugan | Adam Sandler, Cole and Dylan Sprouse, Joey Lauren Adams, Jon Stewart, Rob Schneider | Comedy | 5 Razzie nominations |
| The Big Kahuna | John Swanbeck | Kevin Spacey, Danny DeVito, Peter Facinelli | Drama | |
| Black and White | James Toback | Robert Downey Jr., Gaby Hoffmann, Jared Leto | Crime | |
| The Blair Witch Project | Daniel Myrick, Eduardo Sánchez | Heather Donahue, Joshua Leonard, Michael C. Williams | Horror | 2 Razzie nominations |
| Blast from the Past | Hugh Wilson | Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek, Dave Foley | Romantic comedy | |
| Blue Streak | Les Mayfield | Martin Lawrence, Luke Wilson, Peter Greene, Dave Chappelle | Comedy, Crime | |
| The Bone Collector | Phillip Noyce | Denzel Washington, Angelina Jolie | Crime | from Jeffery Deaver novel |
| The Boondock Saints | Troy Duffy | Willem Dafoe, Sean Patrick Flanery, Norman Reedus | Action | |
| Bowfinger | Frank Oz | Steve Martin, Eddie Murphy, Heather Graham | Comedy | |
| Boys Don't Cry | Kimberly Peirce | Hilary Swank, Chloë Sevigny | Drama | Oscar for Swank |
| Breakfast of Champions | Alan Rudolph | Bruce Willis, Albert Finney, Nick Nolte, Barbara Hershey, Lukas Haas, Omar Epps, Glenne Headly | Comedy | |
| Bringing Out the Dead | Martin Scorsese | Nicolas Cage, Patricia Arquette, John Goodman | Thriller | from Joe Connelly novel |
| Brokedown Palace | Jonathan Kaplan | Claire Danes, Kate Beckinsale, Bill Pullman, Lou Diamond Phillips | Drama | |
| But I'm a Cheerleader | Jamie Babbit | Natasha Lyonne, Cathy Moriarty, RuPaul, Clea DuVall | Comedy | |
| Chill Factor | Hugh Johnson | Cuba Gooding Jr., Skeet Ulrich | Action, Comedy | |
| Chutney Popcorn | Nisha Ganatra | Nisha Ganatra, Jill Hennessy, Madhur Jaffrey | Comedy, Drama | |
| The Cider House Rules | Lasse Hallström | Tobey Maguire, Michael Caine, Charlize Theron, Paul Rudd, Delroy Lindo, Jane Alexander, Kathy Baker | Drama | based on John Irving novel; Academy Award for Caine |
| Coming Soon | Colette Burson | Bonnie Root, Gaby Hoffmann, Mia Farrow | Romantic comedy | |
| The Corruptor | James Foley | Chow Yun-fat, Mark Wahlberg, Ric Young | Action | |
| Cradle Will Rock | Tim Robbins | Hank Azaria, Rubén Blades, Joan Cusack, John Cusack | Drama | |
| Crazy in Alabama | Antonio Banderas | Melanie Griffith, Lucas Black, David Morse, Meat Loaf Aday | Drama | |
| The Crimson Code | Jeremy Haft | Patrick Muldoon, Cathy Moriarty, C. Thomas Howell, Fred Ward | Thriller | aka Red Team |
| Cruel Intentions | Roger Kumble | Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair, Joshua Jackson, Christine Baranski, Swoosie Kurtz | Drama | based on Les Liaisons dangereuses |
| Deep Blue Sea | Renny Harlin | Saffron Burrows, Thomas Jane, LL Cool J, Jacqueline McKenzie, Michael Rapaport, Stellan Skarsgård, Aida Turturro, Samuel L. Jackson | Horror | |
| The Deep End of the Ocean | Ulu Grosbard | Michelle Pfeiffer, Treat Williams, Whoopi Goldberg | Drama | |
| Deterrence | Rod Lurie | Kevin Pollak, Timothy Hutton, Sean Astin | Thriller | Lurie's first film |
| Detroit Rock City | Adam Rifkin | Giuseppe Andrews, James DeBello, Edward Furlong, Sam Huntington, Lin Shaye, Melanie Lynskey | Comedy | inspired by the rock band Kiss |
| ' | Mike Mitchell | Rob Schneider | Comedy | first Happy Madison film |
| Dick | Andrew Fleming | Kirsten Dunst, Michelle Williams, Dan Hedaya | Comedy | |
| Dill Scallion | Jordan Brady | Billy Burke, Lauren Graham | Mockumentary | |
| A Dog of Flanders | Kevin Brodie | Jack Warden, Jon Voight, Cheryl Ladd | Family | |
| Dogma | Kevin Smith | Ben Affleck, Matt Damon, Linda Fiorentino, Salma Hayek, Jason Lee, Alan Rickman, Chris Rock, Kevin Smith | Comedy | View Askew Productions |
| Double Jeopardy | Bruce Beresford | Tommy Lee Jones, Ashley Judd, Bruce Greenwood, Annabeth Gish | Thriller | |
| Drop Dead Gorgeous | Michael Patrick Jann | Kirstie Alley, Ellen Barkin, Kirsten Dunst, Denise Richards | Mockumentary | Amy Adams' first film |
| Dudley Do-Right | Hugh Wilson | Brendan Fraser, Sarah Jessica Parker, Alfred Molina | Comedy | based on cartoon |
| EDtv | Ron Howard | Matthew McConaughey, Jenna Elfman, Woody Harrelson, Elizabeth Hurley, Ellen DeGeneres, Sally Kirkland, Rob Reiner, Dennis Hopper, Martin Landau | Comedy | Imagine Entertainment |
| Election | Alexander Payne | Reese Witherspoon, Matthew Broderick, Chris Klein, Molly Hagan | Comedy | from Tom Perrotta novel |
| End of Days | Peter Hyams | Arnold Schwarzenegger, Robin Tunney, Gabriel Byrne, Kevin Pollak, Udo Kier, C. C. H. Pounder, Miriam Margolyes, Rod Steiger | Horror | |
| Entrapment | Jon Amiel | Sean Connery, Catherine Zeta-Jones, Ving Rhames | Crime drama | 2 Razzie nominations |
| Entropy | Phil Joanou | Stephen Dorff, Judith Godrèche, Kelly Macdonald | Biopic | |
| eXistenZ | David Cronenberg | Jennifer Jason Leigh, Jude Law, Ian Holm | Science fiction Thriller | |
| Eye of the Beholder | Stephan Elliott | Ewan McGregor, Ashley Judd | Thriller | from Marc Behm novel |
| Eyes Wide Shut | Stanley Kubrick | Tom Cruise, Nicole Kidman, Sydney Pollack | Drama | Kubrick's final film |
| Fantasia 2000 | James Levine, Chicago Symphony Orchestra | Family, Animated | sequel to 1940 film | |
| Fight Club | David Fincher | Brad Pitt, Edward Norton, Helena Bonham Carter | Thriller | from Chuck Palahniuk novel |
| Flawless | Joel Schumacher | Robert De Niro, Philip Seymour Hoffman, Chris Bauer | Drama | |
| The Florentine | Nick Stagliano | Jeremy Davies, Virginia Madsen, Luke Perry | Drama | |
| For Love of the Game | Sam Raimi | Kevin Costner, Kelly Preston, John C. Reilly, Jena Malone, Brian Cox | Drama | from Michael Shaara novel |
| Forces of Nature | Bronwen Hughes | Ben Affleck, Sandra Bullock, Steve Zahn | Comedy | |
| Friends & Lovers | George Haas | Stephen Baldwin, Claudia Schiffer, Robert Downey Jr. | Romance | |
| Galaxy Quest | Dean Parisot | Tim Allen, Alan Rickman, Sigourney Weaver, Tony Shalhoub, Sam Rockwell, Daryl Mitchell | Science fiction, Comedy | DreamWorks |
| The General's Daughter | Simon West | John Travolta, Madeleine Stowe, James Woods, Timothy Hutton, James Cromwell, Clarence Williams III | Crime drama | from Nelson DeMille novel |
| ' | Jim Jarmusch | Forest Whitaker | Action | |
| Girl, Interrupted | James Mangold | Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy, Vanessa Redgrave, Whoopi Goldberg | Drama | Oscar for Jolie |
| Gloria | Sidney Lumet | Sharon Stone, Jeremy Northam, Cathy Moriarty, George C. Scott | Crime drama | remake of 1999 film |
| Go | Doug Liman | Sarah Polley, Desmond Askew, Scott Wolf, Katie Holmes, Jay Mohr, Taye Diggs | Comedy | |
| The Green Mile | Frank Darabont | Tom Hanks, David Morse, Bonnie Hunt, Michael Clarke Duncan | Drama | from Stephen King story |
| Guinevere | Audrey Wells | Stephen Rea, Sarah Polley, Gina Gershon | Drama | |
| Happy, Texas | Mark Illsley | Steve Zahn, Jeremy Northam, Ally Walker, Illeana Douglas, William H. Macy | Comedy | |
| The Haunting | Jan de Bont | Liam Neeson, Catherine Zeta-Jones, Lili Taylor, Owen Wilson | Horror | remake of 1963 film; 5 Razzie nominations |
| Heaven or Vegas | Gregory C. Haynes | Richard Grieco, Yasmine Bleeth, Andy Romano | Drama | |
| Held Up | Steve Rash | Jamie Foxx, Nia Long, Barry Corbin | Comedy | |
| The Hi-Line | Ron Judkins | Rachael Leigh Cook, Ryan Alosio | Drama | |
| House on Haunted Hill | William Malone | Geoffrey Rush, Famke Janssen, Taye Diggs, Peter Gallagher, Chris Kattan, Ali Larter, Bridgette Wilson, Max Perlich | Horror | remake of 1959 film |
| The Hurricane | Norman Jewison | Denzel Washington | Drama, Biopic | story of "Hurricane" Carter |
| An Ideal Husband | Oliver Parker | Rupert Everett, Cate Blanchett, Minnie Driver, Julianne Moore, Jeremy Northam | Comedy | |
| Idle Hands | Rodman Flender | Devon Sawa, Seth Green, Jessica Alba, Vivica A. Fox, Elden Henson | Horror comedy | |
| In Dreams | Neil Jordan | Annette Bening, Katie Sagona, Aidan Quinn, Robert Downey Jr., Stephen Rea | Thriller | |
| In Too Deep | Michael Rymer | Omar Epps, LL Cool J, Stanley Tucci, Pam Grier | Crime | |
| The Insider | Michael Mann | Al Pacino, Russell Crowe, Christopher Plummer, Philip Baker Hall, Michael Gambon, Wings Hauser, Gina Gershon | Drama, Biopic | story of Jeffrey Wigand; 7 Oscar nominations |
| Inspector Gadget | David Kellogg | Matthew Broderick, Rupert Everett, Joely Fisher, Michelle Trachtenberg, Andy Dick | Action-Comedy, Family | based on animated series |
| Instinct | Jon Turteltaub | Anthony Hopkins, Cuba Gooding Jr., Donald Sutherland, Maura Tierney | Drama | |
| The Iron Giant | Brad Bird | Jennifer Aniston, Harry Connick Jr., Vin Diesel | Animation, Science fiction, Drama, Family | |
| Jakob the Liar | Peter Kassovitz | Robin Williams, Alan Arkin, Liev Schreiber | Comedy, Drama | |
| Jawbreaker | Darren Stein | Rose McGowan, Rebecca Gayheart, Julie Benz | Comedy,Horror | |
| Jesus' Son | Alison Maclean | Billy Crudup, Samantha Morton, Denis Leary, Holly Hunter | Drama | |
| Joe the King | Frank Whaley | Noah Fleiss, Val Kilmer, Karen Young, Ethan Hawke | Drama | |
| Just a Little Harmless Sex | Rick Rosenthal | Alison Eastwood, Rachel Hunter, Lauren Hutton | Romantic comedy | |
| Just the Ticket | Richard Wenk | Andy García, Andie MacDowell | Romantic comedy | |
| K-911 | Charles T. Kanganis | James Belushi, Christine Tucci, James Handy | Crime Comedy | |
| The King and I | Richard Rich | Miranda Richardson, Martin Vidnovic, Ian Richardson | Animated | |
| Kiss the Sky | Roger Young | William Petersen, Gary Cole, Sheryl Lee, Terence Stamp | Drama | |
| Kiss Toledo Goodbye | Lyndon Chubbuck | Michael Rapaport, Christopher Walken, Christine Taylor | Comedy | |
| Lake Placid | Steve Miner | Bill Pullman, Bridget Fonda, Oliver Platt, Brendan Gleeson, Betty White | Horror Comedy | |
| Liberty Heights | Barry Levinson | Adrien Brody, Ben Foster, Orlando Jones | Drama | |
| Life | Ted Demme | Eddie Murphy, Martin Lawrence, Bernie Mac | Comedy | |
| Light It Up | Craig Bolotin | Usher Raymond, Forest Whitaker, Judd Nelson | Drama | |
| The Limey | Steven Soderbergh | Terence Stamp, Lesley Ann Warren, Luis Guzmán, Peter Fonda | Crime drama | |
| Lost & Found | Jeff Pollack | David Spade, Sophie Marceau, Martin Sheen | Comedy | |
| The Love Letter | Peter Chan | Kate Capshaw, Ellen DeGeneres, Tom Everett Scott, Tom Selleck | Romantic Comedy | |
| Love Stinks | Jeff Franklin | French Stewart, Bridgette Wilson, Bill Bellamy | Comedy | |
| Lovers Lane | John Steven Ward | Erin J. Dean, Riley Smith, Sarah Lancaster | Horror | |
| Lycanthrope | Bob Cook | Robert Carradine, Michael Winslow, Rebecca Holden | Horror | |
| Magnolia | Paul Thomas Anderson | Tom Cruise, Julianne Moore, Philip Seymour Hoffman, Philip Baker Hall, John C. Reilly, William H. Macy, Jason Robards, Jeremy Blackman, Melora Walters, Melinda Dillon, Henry Gibson | Drama | 3 Oscar nominations; Golden Globe award for Cruise |
| Man of the Century | Adam Abraham | Gibson Frazier, Cara Buono, Susan Egan | Comedy | |
| Man on the Moon | Miloš Forman | Jim Carrey, Danny DeVito, Courtney Love, Paul Giamatti | Biopic | life of Andy Kaufman |
| A Map of the World | Scott Eliott | Sigourney Weaver, Julianne Moore, David Strathairn | Drama | |
| The Mating Habits of the Earthbound Human | Jeff Abugov | Carmen Electra, Mackenzie Astin, Lucy Liu | Mockumentary | |
| The Matrix | Andy Wachowski, Larry Wachowski | Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving, Joe Pantoliano | Science fiction | won 4 Oscars |
| Message in a Bottle | Luis Mandoki | Kevin Costner, Robin Wright Penn, Paul Newman | Romantic drama | |
| ' | Luc Besson | Milla Jovovich, John Malkovich, Faye Dunaway, Dustin Hoffman | Biopic | |
| Mickey Blue Eyes | Kelly Makin | Hugh Grant, James Caan, Jeanne Tripplehorn | Comedy | Castle Rock |
| A Midsummer Night's Dream | Michael Hoffman | Kevin Kline, Michelle Pfeiffer, Rupert Everett, Stanley Tucci, Calista Flockhart, Anna Friel, Christian Bale | Shakespearean | |
| Miss Julie | Mike Figgis | Saffron Burrows, Peter Mullan, Maria Doyle Kennedy | Drama | |
| The Mod Squad | Scott Silver | Claire Danes, Omar Epps, Giovanni Ribisi | Action | based on TV series |
| ' | Errol Morris | Fred A. Leuchter, David Irving, Ernst Zündel | Documentary | |
| Mumford | Lawrence Kasdan | Loren Dean, Jason Lee, Hope Davis, Alfre Woodard, Mary McDonnell, Ted Danson, Martin Short, Zooey Deschanel, Pruitt Taylor Vince | Comedy | Touchstone Pictures |
| The Mummy | Stephen Sommers | Brendan Fraser, Rachel Weisz, John Hannah, Oded Fehr, Arnold Vosloo | Action | remake of 1932 film |
| Muppets from Space | Tim Hill | Dave Goelz, Steve Whitmire, Bill Barretta, Frank Oz | Comedy | |
| The Muse | Albert Brooks | Albert Brooks, Sharon Stone, Andie MacDowell, Jeff Bridges | Comedy | |
| Music of the Heart | Wes Craven | Meryl Streep, Angela Bassett, Aidan Quinn, Gloria Estefan | Drama | |
| My Favorite Martian | Donald Petrie | Christopher Lloyd, Jeff Daniels, Elizabeth Hurley, Daryl Hannah, Wallace Shawn, Ray Walston | Comedy | based on TV series |
| My Voyage to Italy | Martin Scorsese | Documentary | ||
| Mystery, Alaska | Jay Roach | Russell Crowe, Burt Reynolds, Colm Meaney | Comedy, Sports | |
| Mystery Men | Kinka Usher | Ben Stiller, Hank Azaria, William H. Macy, Janeane Garofalo, Wes Studi, Paul Reubens, Kel Mitchell, Greg Kinnear, Geoffrey Rush, Lena Olin, Claire Forlani, Tom Waits | Superhero Comedy | |
| Never Been Kissed | Raja Gosnell | Drew Barrymore, David Arquette, Molly Shannon, James Franco | Comedy | Franco's first film |
| The Ninth Gate | Roman Polanski | Johnny Depp, Lena Olin, Frank Langella | Horror | |
| Ninth Street | Tim Rebman | Don Washington | Drama | |
| Notting Hill | Roger Michell | Julia Roberts, Hugh Grant, Hugh Bonneville, Emma Chambers, James Dreyfus, Rhys Ifans, Tim McInnerny, Gina McKee | Romantic comedy | BAFTA award; 3 Golden Globe nominations |
| October Sky | Joe Johnston | Jake Gyllenhaal, Chris Cooper, Laura Dern | Drama | story of Homer Hickam |
| Office Space | Mike Judge | Ron Livingston, Jennifer Aniston, Stephen Root, Gary Cole | Comedy | based on Judge's cartoons |
| The Omega Code | Robert Marcarelli | Casper Van Dien, Michael York | Action | |
| One Man's Hero | Lance Hool | Tom Berenger, Joaquim de Almeida, Daniela Romo | War | |
| The Other Sister | Garry Marshall | Juliette Lewis, Diane Keaton, Tom Skerritt, Giovanni Ribisi | Drama | |
| Our Friend, Martin | Rob Smiley, Vincenzo Trippetti | Animated | ||
| P.U.N.K.S. | Sean McNamara | Tim Redwine, Jessica Alba, Brandon Baker | Teen comedy | |
| The Passion of Ayn Rand | Christopher Menaul | Helen Mirren, Eric Stoltz, Peter Fonda | Biography | based on Barbara Branden book; made for TV |
| Passport to Paris | Alan Metter | Mary-Kate Olsen, Ashley Olsen | Romantic comedy | |
| Payback | Brian Helgeland | Mel Gibson, Gregg Henry, Maria Bello, Lucy Liu | Crime drama | Inspired by Point Blank |
| Play It to the Bone | Ron Shelton | Antonio Banderas, Woody Harrelson, Lolita Davidovich, Lucy Liu | Comedy, Drama | |
| Pushing Tin | Mike Newell | John Cusack, Billy Bob Thornton, Cate Blanchett, Angelina Jolie | Comedy, Drama | |
| ' | Katt Shea | Emily Bergl, Mena Suvari, Jason London, Amy Irving | Horror | |
| Random Hearts | Sydney Pollack | Harrison Ford, Kristin Scott Thomas, Charles S. Dutton | Drama | |
| Ravenous | Antonia Bird | Guy Pearce, Robert Carlyle, Jeremy Davies, Jeffrey Jones, John Spencer, Stephen Spinella, Neal McDonough, David Arquette | Horror | Czech/U.K./U.S. |
| Retro Puppet Master | David DeCoteau | Greg Sestero, Brigitta Dau, Jack Donner | Horror | |
| Revelation aka Apocalypse | Andre van Heerden | Thriller | ||
| Rites of Passage | Victor Salva | Dean Stockwell, James Remar, Jason Behr | Drama | |
| Runaway Bride | Garry Marshall | Richard Gere, Julia Roberts, Joan Cusack | Romantic comedy | |
| The Runner | Ron Moler | Ron Eldard, Courteney Cox, John Goodman | Thriller | |
| She's All That | Robert Iscove | Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O'Keefe, Kieran Culkin, Anna Paquin | Romantic comedy | |
| Simon Sez | Kevin Elders | Dennis Rodman, Dane Cook | Action, Comedy | |
| Simply Irresistible | Mark Tarlov | Sarah Michelle Gellar, Sean Patrick Flanery, Patricia Clarkson | Romantic comedy | |
| The Sixth Sense | M. Night Shyamalan | Bruce Willis, Haley Joel Osment, Toni Collette, Donnie Wahlberg, Olivia Williams | Suspense | 5 Oscar nominations |
| Sleepy Hollow | Tim Burton | Johnny Depp, Christina Ricci, Miranda Richardson, Casper Van Dien | Horror | from Washington Irving novel |
| A Slipping-Down Life | Toni Kalem | Lili Taylor, Guy Pearce | Romance | |
| Snow Falling on Cedars | Scott Hicks | Ethan Hawke, Youki Kudoh, Reeve Carney | Drama | David Guterson novel |
| ' | Trey Parker | Trey Parker, Matt Stone, Mary Kay Bergman, Isaac Hayes | Animation, musical, Comedy | Based on TV series |
| Speedway Junky | Nickolas Perry | Jesse Bradford, Jordan Brower, Daryl Hannah | Action | |
| ' | George Lucas | Liam Neeson, Ewan McGregor, Natalie Portman, Jake Lloyd | Space opera | prequel to Star Wars; top-grossing film of 1999; 3 Oscar nominations |
| Stigmata | Rupert Wainwright | Patricia Arquette, Gabriel Byrne, Jonathan Pryce | Horror | |
| Stir of Echoes | David Koepp | Kevin Bacon, Kathryn Erbe, Illeana Douglas | Horror | |
| Storm | Andrew Hofman | Christian McIntire, Luke Perry, Robert Knott, Alexandra Powers | Thriller | |
| The Story of Us | Rob Reiner | Bruce Willis, Michelle Pfeiffer | Romantic drama | |
| The Straight Story | David Lynch | Richard Farnsworth, Sissy Spacek, Harry Dean Stanton | Drama | |
| Stuart Little | Rob Minkoff | Geena Davis, Hugh Laurie, Jonathan Lipnicki | Family | from E. B. White story |
| Summer of Sam | Spike Lee | John Leguizamo, Adrien Brody, Mira Sorvino, Jennifer Esposito | Crime drama | |
| Superstar | Bruce McCulloch | Molly Shannon, Will Ferrell, Harland Williams | Comedy | Saturday Night Live character |
| Sweet and Lowdown | Woody Allen | Sean Penn, Samantha Morton, Anthony LaPaglia, Uma Thurman | Comedy | |
| The Talented Mr. Ripley | Anthony Minghella | Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett, Philip Seymour Hoffman, Philip Baker Hall, James Rebhorn | Thriller | from Patricia Highsmith novel; 5 Oscar nominations |
| Tarzan | Kevin Lima and Chris Buck | Tony Goldwyn, Minnie Driver, Glenn Close, Rosie O'Donnell, Brian Blessed, Nigel Hawthorne, Lance Henriksen, Wayne Knight | Animation | from character created by Edgar Rice Burroughs |
| Teaching Mrs. Tingle | Kevin Williamson | Helen Mirren, Katie Holmes, Barry Watson, Marisa Coughlan | Drama | |
| That Championship Season | Paul Sorvino | Gary Sinise, Vincent D'Onofrio, Tony Shalhoub, Terry Kinney, Paul Sorvino | Drama | based on Jason Miller play; remake of 1982 film |
| Thicker than Water | Richard Cummings Jr. | Mack 10, Fat Joe, Ice Cube | Drama | |
| The Thirteenth Floor | Josef Rusnak | Craig Bierko, Gretchen Mol, Vincent D'Onofrio | Science fiction | |
| The Thirteenth Year | Duwayne Dunham | Chez Starbuck, Courtnee Draper | Family | |
| The Thomas Crown Affair | John McTiernan | Pierce Brosnan, Rene Russo, Denis Leary | Crime | remake of 1968 film |
| Three Kings | David O. Russell | George Clooney, Mark Wahlberg, Ice Cube, Spike Jonze | War, Comedy | |
| Three to Tango | Damon Santostefano | Matthew Perry, Neve Campbell, Dylan McDermott | Romantic comedy | |
| Titus | Julie Taymor | Anthony Hopkins, Jessica Lange, Alan Cumming | Shakespearean | |
| Toy Story 2 | John Lasseter, Lee Unkrich, Ash Brannon | voices of Tom Hanks, Tim Allen, Annie Potts, Don Rickles | Animation Comedy Family | sequel to Toy Story |
| Trippin | David Raynr | Deon Richmond, Countess Vaughn, Maia Campbell | Comedy | |
| True Crime | Clint Eastwood | Clint Eastwood, Isaiah Washington, Denis Leary | Crime drama | |
| Tumbleweeds | Gavin O'Connor | Janet McTeer, Kimberly J. Brown, Gavin O'Connor | Drama | |
| Twin Falls Idaho | Michael Polish | Mark Polish, Michael Polish, Michele Hicks | Drama | |
| ' | Mic Rodgers | Jean-Claude Van Damme, Michael Jai White | Action | |
| Varsity Blues | Brian Robbins | James Van Der Beek, Jon Voight, Paul Walker, Amy Smart, Scott Caan, Ron Lester, Ali Larter, Eliel Swinton | Comedy, Drama, Sports | won MTV, Teen Choice film awards |
| The Virgin Suicides | Sofia Coppola | James Woods, Kathleen Turner, Kirsten Dunst, Josh Hartnett, A. J. Cook | Drama | from Jeffrey Eugenides novel |
| Virus | John Bruno | Jamie Lee Curtis, William Baldwin, Donald Sutherland | Science fiction, Horror | |
| The Waiting Game | Ken Liotti | Will Arnett, Dwight Ewell | Comedy | |
| Wakko's Wish | 3 directors | Animation | ||
| A Walk on the Moon | Tony Goldwyn | Diane Lane, Viggo Mortensen, Liev Schreiber, Anna Paquin | Drama | Miramax |
| Walking Across Egypt | Arthur Allan Seidenman | Ellen Burstyn, Jonathan Taylor Thomas, Mark Hamill | Comedy | |
| When the Day Breaks | Wendy Tilby, Amanda Forbis | Animated | Short film | |
| Whiteboyz | Danny Hoch | Independent | ||
| Wild Wild West | Barry Sonnenfeld | Will Smith, Kevin Kline, Kenneth Branagh, Salma Hayek | Action, Comedy | based on TV series; winner of 5 Razzie awards |
| Wing Commander | Chris Roberts | Freddie Prinze Jr., Saffron Burrows, Matthew Lillard, Tchéky Karyo, Jürgen Prochnow, David Suchet | Science fiction | |
| ' | 3 directors | Jim Cummings, John Fiedler, Brady Bluhm | Animation | A. A. Milne characters |
| Wisconsin Death Trip | ||||
| The Woman Chaser | Robinson Devor | Patrick Warburton | Comedy | |
| A Woman Scorned | Treva Etienne | Marcia Johnson | Thriller | |
| The Wood | Rick Famuyiwa | Omar Epps, Richard T. Jones, Taye Diggs | Comedy | |
| The World Is Not Enough'' | Michael Apted | Pierce Brosnan, Sophie Marceau, Robert Carlyle | Spy action |