Pretty and popular, Bianca Stratford (Larisa Oleynik) desperately wants to date Joey Donner (Andrew Keegan), the high school heartthrob. The only problem is that Bianca's father (Larry Miller) has forbidden her to date anyone until her cynical, sharp-tongued older sister, Kat (Julia Stiles), finds a date of her own. When Cameron James (Joseph Gordon-Levitt), a new student who likes Bianca, learns of the situation, he teams up with Joey to bribe Patrick (Heath Ledger), a mysterious loner, to ask Kat out, and thus free Bianca to date whomever she wants. Directed by Gil Junger. With David Krumholtz, Susan May Pratt, Gabrielle Union, Daryl Mitchell and Allison Janney. Categories: Comedy, Drama, Romance. Year: 1999.

1999 in 10 Things I Hate About You
When an Arab courtier (Antonio Banderas) accompanies a group of Vikings back to their homeland, he is disgusted by their sex-driven and animalistic culture. Believing himself a simple visitor, he soon realizes that he has instead been conscripted to fight a horrifying evil that murders the Vikings and eats the dead. Directed by John McTiernan. With Vladimir Kulich, Omar Sharif and Daniel Southern. Categories: Action, Adventure, Fantasy. Year: 1999.

1999 in The 13th Warrior
In the process of coming to terms with the tragic loss of her only son, Esteban (Eloy Azorín), Manuela (Cecilia Roth) leaves Madrid and goes to Barcelona to find the boy's father, a transvestite named Lola (Toni Cantó). But first, she finds her transvestite friend, Agrado (Antonia San Juan), meets Rosa (Penélope Cruz), a young nun bound for El Salvador, and by happenstance, becomes the personal assistant of Huma Rojo (Marisa Paredes), the actress her son admired. Directed by Pedro Almodóvar. Categories: Drama, Foreign Film. Year: 1999.

1999 in All About My Mother
Lester Burnham (Kevin Spacey) has a perfect wife (Annette Bening) and a perfect house in the perfect neighborhood. Lester, however, is miserable. In the throws of a midlife crisis, Lester watches his marriage dissolve and his own interest grow in one of his daughter's high school friends (Mena Suvari). As his daughter (Thora Birch) develops a friendship with the boy (Wes Bentley) next door and his wife begins an affair, Lester looks deeper inside himself for a cure to his unhappiness. Directed by Sam Mendes. Categories: Drama. Year: 1999.

1999 in American Beauty
Directed by Chris Weitz. With Jason Biggs, Thomas Ian Nicholas, Eddie Kaye Thomas, Eugene Levy, Chris Klein, Natasha Lyonne, Shannon Elizabeth, Alyson Hannigan, Seann William Scott and Tara Reid. Categories: Comedy, Romance. Year: 1999.

1999 in American Pie
Paul Vitti (Robert De Niro), a cold-blooded mob boss who has been suffering from anxiety attacks, looks to psychiatrist Ben Sobol (Billy Crystal) to help him sort things out. Sobel isn't thrilled with the idea of working for a criminal but, after being persuaded by Vitti, he decides it's in his best interests to assist his new client. As Vitti's problems escalate, Sobol does his best to satisfy the needy mobster, while contending with the demands of his bride-to-be (Lisa Kudrow). Directed by Harold Ramis. With Chazz Palminteri. Categories: Comedy, Crime. Year: 1999.

1999 in Analyze This
Cap Rooney (Dennis Quaid) is a football legend and a star quarterback at the top of his game. When a damaging hit forces Rooney to the sidelines, coach Tony D'Amato (Al Pacino) has to find a replacement. Backup Willie Beaman (Jamie Foxx), a benchwarmer with one last chance to prove himself, gets the nod, but his performance and attitude threaten to destroy the team. Off the field, D'Amato must contend with new owner Christina Pagniacci (Cameron Diaz), who blames the old school coach for the teams lack of success. Directed by Oliver Stone. With James Woods, Matthew Modine and LL Cool J. Categories: Drama, Sports. Year: 1999.

1999 in Any Given Sunday
For two minutes, astronaut Spencer Armacost (Johnny Depp) loses total consciousness while on a routine space shuttle mission, returning to Earth barely alive. The President, the nation and his friends celebrate his safe homecoming, but his wife Jillian (Charlize Theron) senses that there is something very different about the man she loves. Directed by Rand Ravich. With Joe Morton and Clea DuVall. Categories: Sci-Fi, Thriller, Horror. Year: 1999.

1999 in The Astronaut's Wife
When Dr. Evil (Mike Myers) decides to travel back to 1969 in order to steal Austin Powers' mojo, Austin (also played by Mike Myers) is left powerless. Partnered with his new right-hand woman, Felicity Shagwell (Heather Graham), Austin must go back in time to get his groove back and stop Dr. Evil from destroying the world with a powerful laser. Directed by Jay Roach. With Michael York, Robert Wagner, Rob Lowe, Seth Green, Mindy Sterling and Verne Troyer. Categories: Comedy, Action, Adventure. Year: 1999.

1999 in Austin Powers: The Spy Who Shagged Me
Craig Schwartz (John Cusack) is an out of work puppeteer with a dowdy girlfriend (Cameron Diaz) and few prospects. After starting a strange new job, he discovers a doorway in his office building that allows him to enter the head of actor John Malkovich for fifteen minutes. This discovery opens up new avenues in his life as he experiments with this bizarre ability. Directed by Spike Jonze. With Catherine Keener, Charlie Sheen, Sean Penn, Winona Ryder and Ned Bellamy. Categories: Comedy, Fantasy, Drama. Year: 1999.

1999 in Being John Malkovich
After receiving a large settlement following a car accident, law school graduate, Sonny Koufax (Adam Sandler) gave in to his slacker nature and settled into an easy life working in a toll booth. When child services shows up at his door one day and drops off Julian (Cole Sprouse and Dylan Sprouse), the five-year-old son of his roomate Kevin (Jon Stewart), who happens to be on a business trip to China, Sonny doesn't know what to do. Eventually, he decides that he can use Julian to win back his ex-girlfriend (Kristy Swanson), who left him because of his lack of motivation and immaturity. While Sonny and Julian initially struggle with their awkward new realtionship, ultimately Julian helps Sonny accept the responsibilities of adulthood and Sonny provides Julian with the loving father he's never had. Directed by Dennis Dugan. With Joey Lauren Adams, Leslie Mann, Allen Covert and Rob Schneider. Categories: Comedy. Year: 1999.

1999 in Big Daddy
Lincoln Rhyme (Denzel Washington) is a quadriplegic ex-detective ready to end it all when a string of gruesome murders convinces him to hold it together long enough to find the killer. Bedridden and totally dependent on his live-in nurse Thelma (Queen Latifah), Lincoln must rely on young detective Amelia Donaghy (Angelina Jolie) to gather the clues, as she contends with her own unsettling past. Directed by Phillip Noyce. With Michael Rooker, Luis Guzmán and Mike McGlone. Categories: Mystery, Drama, Thriller. Year: 1999.

1999 in The Bone Collector
After accidentally killing some mafia thugs, two Irish Catholic brothers, Conner (Sean Patrick Flanery) and Murphy MacManus (Norman Reedus), turn themselves in to police but are released as heroes. Encouraged by the public's praise, the brothers see it as a calling from God and start taking out mafia gang members one by one. Willem Dafoe plays the FBI detective investigating the case. Directed by Troy Duffy. Categories: Crime, Drama, Thriller. Year: 1999.

1999 in The Boondock Saints
Directed by Kimberly Peirce. With Hilary Swank and Chlo_ Sevigny. Categories: Crime, Drama, Romance. Year: 1999.

1999 in Boys Don't Cry
Homer Wells (Tobey Maguire) grows up in an orphanage and becomes a skilled physician under the tutelage of his mentor, Dr. Larch (Michael Caine). Desiring a life outside the only home he has ever known, Homer falls in love for the first time and faces difficult decisions force him to realize that he will never fully escape his past. Directed by Lasse Hallström. With Charlize Theron, Delroy Lindo, Paul Rudd, Kieran Culkin and Erykah Badu. Categories: Drama, Romance. Year: 1999.

1999 in The Cider House Rules
Decorated policeman Nick Chen (Yun-Fat Chow) is assigned to defuse a turf war in Chinatown between the Triads and the Fukienese Dragons. As the action heats up, Chen is teamed up with young cop Danny Wallace (Mark Wahlberg), who is unaware of how power and influence have compromised his superiors. When Wallace is offered a bribe, Chen is forced to realign the loyalties that have helped him rise through the ranks. Directed by James Foley. With Brian Cox. Categories: Action, Crime, Drama, Mystery, Thriller. Year: 1999.

1999 in The Corruptor
Deuce Bigalow (Rob Schneider), a kind-hearted, incompetent fish tank cleaner, gets the opportunity of a lifetime when Antoine (Oded Fehr), a suave, successful male gigolo, asks him to watch over his beautiful home and precious fish while he is away on business. However, Deuce quickly finds a way to reverse his good fortune, and is forced to become the world's most unlikely male escort in order to pay for the damage he's caused at Antoine's. Neck-deep in a world he never knew existed, Deuce receives tips and encouragement from T.J. (Eddie Griffin), his pimp, and hits the town to dispense his unique brand of pleasure. Directed by Mike Mitchell. With William Forsythe, Amy Poehler and Allen Covert. Categories: Comedy. Year: 1999.

1999 in Deuce Bigalow: Male Gigolo
When high school best friends Betsy Jobs (Kirsten Dunst) and Arlene Lorenzo (Michelle Williams) wander off during a class trip to the White House and stumble into a room filled with presidential secrets, the Secret Service tracks them down and brings them to President Richard Nixon (Dan Hedaya). Intent on finding out just how much they know, Dick appoints them as official White House dog walkers. Initially, the President is able to convince the impressionable girls that everything is on the up and up. But, after they develop a strange but close relationship with the Commander in Chief, the girls eventually learn the truth about the Watergate scandal and contact newspaper reporters Bob Woodward (Will Ferrell) and Carl Bernstein (Bruce McCulloch). Directed by Andrew Fleming. With Ryan Reynolds and Dave Foley. Category: Comedy. Year: 1999.

1999 in Dick
Bethany Sloane (Linda Fiorentino), an abortion clinic worker who happens to be the last descendant of Jesus Christ, is called upon to save humanity from two fallen angels (Ben Affleck and Matt Damon) who have found a loophole that will send them back to heaven, and thus end all of existence. Initially skeptical and reluctant, Bethany eventually accepts her destiny and is aided in her quest by two unlikely prophets, Jay (Jason Mewes) and Silent Bob (Kevin Smith), Rufus (Chris Rock), the 13th apostle, and Serendipity (Salma Hayek), a vivacious muse. Standing is Bethany's way is Azrael (Jason Lee), a demon with a personal vendetta against God. Directed by Kevin Smith. With Alan Rickman, Janeane Garofalo, George Carlin and Alanis Morissette. Categories: Comedy, Adventure, Fantasy, Romance. Year: 1999.

1999 in Dogma
Libby Parsons (Ashley Judd) is framed for her husband Nick’s (Bruce Greenwood) murder. After spending seven years in jail, she is released, armed with several important pieces of information: her husband is still alive, her son (Benjamin Weir) was put up for adoption, and if she kills her husband she cannot be tried for the crime. With the help of her parole officer, Travis (Tommy Lee Jones), the enraged Libby embarks on a journey to find her son and avenge the wrongs done to her. Directed by Bruce Beresford. With Jay Brazeau, John Maclaren, Roma Maffia and Annabeth Gish. Categories: Thriller, Drama, Mystery, Crime. Year: 1999.

1999 in Double Jeopardy
With a television crew covering a Minnesota town's annual beauty pageant, Gladys Leeman (Kirstie Alley), a former winner, desperately wants her daughter, Becky (Denise Richards), to follow in her footsteps. And, she's willing to do just about anything to make sure that it happens. But, despite Gladys' tampering, Becky's main competition, Amber Atkins (Kirsten Dunst), won't stop pursuing her dreams. Directed by Michael Patrick Jann. With Ellen Barkin, Allison Janney, Brittany Murphy and Amy Adams. Categories: Comedy. Year: 1999.

1999 in Drop Dead Gorgeous
Virginia Baker (Catherine Zeta-Jones), an undercover government agent, convinces master thief Robert Macdougal (Sean Connery) to take her on as a student. As their relationship develops, Baker's loyalty to her organization begins to waver as she and Macdougal contend with their growing romance while training for a complicated heist. Directed by Jon Amiel. With Ving Rhames, Will Patton, Terry O'Neill and David Yip. Categories: Comedy, Crime, Thriller, Romance. Year: 1999.

1999 in Entrapment
After his wife Alice (Nicole Kidman) admits to having sexual fantasies about a man she saw briefly while the two were vactioning in Cape Cod, Dr. Bill Harford (Tom Cruise) is haunted by the idea of his wife being with another man. Pushed to an emotional brink, Bill finds himself in increasingly sexually charged situations as he succombs to an obsession with living out his fantasies. Eventually, Bill finds himself at a mysterious party at a huge mansion where masked participants engage in group sex. After being discovered as an outsider, Bill realizes that he is in over his head and that his life and marriage are in grave danger. Directed by Stanley Kubrick. With Sydney Pollack and Todd Field. Categories: Drama, Mystery, Thriller. Year: 1999.

1999 in Eyes Wide Shut
The narrator (Edward Norton), a product liability evaluator and insomniac who is addicted to self-help groups, is liberated from his cookie-cutter, mail-order life after meeting Tyler Durden (Brad Pitt), a sado-masochistic anarchist who runs a nationwide network of fight clubs. As their friendship grows, the narrator discovers that Durden is secretly plotting a series of calculated pranks and terrorist attcks in order to overthrow the capitalist system. As the narrator struggles with a decision between right and wrong, his relationship with a fellow self-helper (Helena Bonham Carter) begins to unravel, along with his grip on reality. Directed by David Fincher. With Meat Loaf, Jared Leto and Zach Grenier. Categories: Cult Classics, Drama, Thriller, Crime, Action. Year: 1999.

1999 in Fight Club
When an alien species visits Earth looking for help, they know who to call: the stars of Galaxy Quest, a once popular TV show whose cast now appears at science fiction conventions. Thinking that the Galaxy Quest stars are actually intergalactic heroes, the aliens recruit the group of washed-up actors to save their world from invasion. Directed by Dean Parisot. With Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub, Sam Rockwell and Daryl Mitchell. Categories: Adventure, Comedy, Sci-Fi. Year: 1999.

1999 in Galaxy Quest
Scandals, cover-ups and sex are at the center of this thriller. John Travolta and Madeleine Stowe play army officers and former lovers who investigate the torture killing of the daughter (Leslie Stefanson) of a prominent general (James Cromwell). Their investigation leads them back to West Point, and to abuses by powerful men. Should they risk their own careers to bring the truth to light? James Woods plays a high-ranking officer with something to hide. Directed by Simon West. Clarence Williams III. Categories: Crime, Drama, Mystery, Thriller. Year: 1999.

1999 in The General's Daughter
Ghost Dog (Forest Whitaker) is an urban warrior who follows the code of the Samurai. He lives alone, only descending from his rooftop home to commit murder for his master, Louie (John Tormey), a mob tough guy who once saved his life. When Ghost Dog becomes a Mafia target himself, he must fight off a stream of killers while trying to protect his master and uphold the Way of the Warrior. Directed by Jim Jarmusch. With Cliff Gorman and Dennis Liu. Categories: Action, Crime, Drama. Year: 1999.

1999 in Ghost Dog: The Way of the Samurai
After a fumbled suicide attempt, recent high school graduate Susanna Kaysen (Winona Ryder) checks into the Claymoore mental institution. Inside, Susanna finds allies in Daisy (Brittany Murphy), a sexually abused teenager, the pathological Georgina (Clea DuVall) and a burn victim named Polly (Elisabeth Moss). However, the biggest influence on Susanna's life is Lisa Rowe (Angelina Jolie), the ringleader of this small band of tortured spirits. Directed by James Mangold. With Whoopi Goldberg, Vanessa Redgrave and Jared Leto. Categories: Drama. Year: 1999.

1999 in Girl, Interrupted
Paul Edgecomb (Tom Hanks) is a decent and hard-working prison guard at Cold Mountain Penitentiary. When John Coffey (Michael Clarke Duncan), who has been convicted of rape and murder, is sent to Cold Mountain's death row, Edgemcomb and the other guards (David Morse and Barry Pepper) sense that Coffey is no ordinary prisoner. When Coffey is discovered to have a special gift, the guards face a moral dilemma in deciding whether or not to carry out their duties. Directed by Frank Darabont. With Bonnie Hunt, James Cromwell, Sam Rockwell, William Sadler, Patricia Clarkson and Gary Sinise. Categories: Crime, Drama, Thriller. Year: 1999.

1999 in The Green Mile
In 1966, Rubin "Hurricane" Carter (Denzel Washington), a middleweight contender, is falsely accused and convicted of a triple murder. Sentenced to life in prison, he copes with his life behind bars by writing the story of his life. Twenty years into his incarceration, high school student Lesra Martin (Vicellous Reon Shannon), inspired by Carter's autobiography, convinces a group of friends and mentors to take up Carter's cause to try and prove his innocence. To set his idol free, Martin and his team not only have to deal with a racist establishment intent on keeping Carter behind bars, but also with Carter's broken spirit and sense of hopelessness. Directed by Norman Jewison. With Dan Hedaya, Clancy Brown, Deborah Kara Unger, Liev Schreiber, John Hannah and David Paymer. Categories: Biography, Drama, Sports, Based on a True Story. Year: 1999.

1999 in The Hurricane
Dr. Jeffrey Wigand (Russell Crowe) knows that the information he holds concerning the truth about cigarette addiction and tobacco industry malpractice could open a floodgate of litigation against Big Tobacco. After Wigand contacts Lowell Bergman (Al Pacino), a producer for CBS's "60 Minutes," the industry sets out to discredit the doctor and shut him down any way they can. With Bergman's backing, Wigand's story finally makes it to the air and the two men form a relationship built upon a shared struggle to reveal the truth despite personal and professional hardships. Directed by Michael Mann. With Christopher Plummer, Michael Gambon and Diane Venora. Categories: Biography, Drama, Thriller. Year: 1999.

1999 in The Insider
After Hogarth Hughes (Eli Marienthal) finds a huge iron robot (voiced by Vin Diesel) tangled in the high-tension wires near his house, the boy rescues the talking, alien machine and the two become fast friends. But, when the Iron Giant starts munching on cars and tractors around town, Hogarth's neighbors start looking for the culprit, and the resulting commotion attracts the attention of a paranoid government agent (Christopher McDonald) who wants to destroy Hogarth's pal. Directed by Brad Bird. With Jennifer Aniston and Harry Connick Jr.. Categories: Animation, Drama, Family, Sci-Fi. Year: 1999.

1999 in The Iron Giant
After his daughter, Jenny (Melissa George), is murdered in Los Angeles, English ex-con Wilson (Terence Stamp) comes to America to find out why. A stranger in a strange land, Wilson teams up with a criminal named Eduardo Roel (Luis Guzmán) to track Terry Valentine (Peter Fonda), a sleazy record producer who was having an affair with Jenny when she was killed. Directed by Steven Soderbergh. With Lesley Ann Warren, Amelia Heinle and Barry Newman. Categories: Crime, Drama, Thriller. Year: 1999.

1999 in The Limey
Nine people who share a connection to a children's game show find their lives intertwined during one random day in the San Fernando Valley. Through a series of chance encounters, coincidences and unforeseen drama, each experiences drastic changes in their lives before a strange and totally unexpected climax. Directed by Paul Thomas Anderson. With Tom Cruise, Julianne Moore, William H. Macy, John C. Reilly, Philip Baker Hall, Philip Seymour Hoffman, Jason Robards, Melora Walters, Jeremy Blackman and Alfred Molina. Categories: Drama. Year: 1999.

1999 in Magnolia
When a hacker named Neo (Keanu Reeves) is contacted by the mysterious rebel leader Morpheus (Laurence Fishburne), he learns a terrifying secret: our world is an illusion created by the Matrix, a hyper-intelligent computer network enslaving the human race for their biological energy. Neo must decide whether to join the fight for freedom, or remain in the comforts of a false reality. Deciding to team up with the few humans who have escaped into the real world, including the beautiful and deadly Trinity (Carrie-Anne Moss), Neo sets out to subvert the forces of the Matrix, led by the sinister Agent Smith (Hugo Weaving), and free humanity. Directed by Andy Wachowski and Larry Wachowski. With Joe Pantoliano and Gloria Foster. Categories: Cult Classics, Action, Thriller, Sci-Fi. Year: 1999.

1999 in The Matrix
Directed by Luis Mandoki. With Robin Wright Penn, Kevin Costner, Paul Newman and Robbie Coltrane. Categories: Drama, Romance. Year: 1999.

1999 in Message in a Bottle
When journalist Josie Geller (Drew Barrymore) is assigned to go undercover and find out what really goes on in today's high schools, she hopes that she will be more popular with her classmates than she was the first time around. But, after enrolling in a local high school, Josie quickly falls back into nerdy habits and finds it difficult to make friends. Things look bleak for Josie until her cool, older brother Rob (David Arquette) shows up and spreads flattering gossip about her, attracting the attention of the coolest kids in school (Jessica Alba and James Franco). Just as things start to go Josie's way, she finds that she is falling for a teacher (Michael Vartan), putting her assignment and career in jeopardy. Directed by Raja Gosnell. With Molly Shannon, John C. Reilly and Garry Marshall. Categories: Comedy, Romance. Year: 1999.

1999 in Never Been Kissed
Can the owner of a small bookstore in London's multi-cultural Notting Hill neighborhood find love with the biggest star in Hollywood? That's the question in Notting Hill, in which Hugh Grant plays the bookstore owner and Julia Roberts is the actress he meets by chance. Grant and Roberts make for a charming couple in this gentle romantic comedy, but Rhys Ifans gets the biggest laughs as Grant's slacker roommate. Directed by Roger Michell. With Richard McCabe, James Dreyfus and Dylan Moran. Categories: Comedy, Romance. Year: 1999.

1999 in Notting Hill
Peter Gibbons (Ron Livingston) is a normal guy in his thirties, sick of the mindless tasks and bureaucratic nonesense that he's subjected to everyday at his job working for a computer software company. To deal with his depression and endless requests from his boss, Bill Lumbergh (Gary Cole), to come in on weekends, Gibbons undergoes hypnotherapy. But, when the hypnotherapist falls over dead before the end of their session, Gibbons stops going to the office and, later, teams up with two of his coworkers to put a virus on their company's network that will allow them to embezzle thousands of dollars. When the plan goes awry, Gibbons has to figure out a way to cover his tracks and explain his erratic behavior to his new girlfriend (Jennifer Aniston). Directed by Mike Judge. With John C. McGinley, Ajay Naidu, David Herman, Diedrich Bader and Stephen Root. Categories: Cult Classics, Comedy. Year: 1999.

1999 in Office Space
Directed by John Myhre. With Mel Gibson, Gregg Henry, James Coburn, David Paymer, Kris Kristofferson and William Devane. Categories: Action, Crime, Thriller. Year: 1999.

1999 in Payback
Nick Falzone (John Cusack) is a hotshot air traffic controller who treats his incredibly serious job like a game, pushing planes around the sky like pieces on a chessboard. No one can match his professional prowess until Russell Bell (Billy Bob Thornton), an accomplished controller in his own right, threatens Nick's job and his relationship with his wife (Cate Blanchett). Directed by Mike Newell. With Angelina Jolie. Categories: Drama, Comedy. Year: 1999.

1999 in Pushing Tin
After being fired for writing a trumped up story about Maggie Carpenter (Julia Roberts), a woman notorious for leaving grooms at the altar, columnist Ike Graham (Richard Gere) tries to get back into the business by tracking Maggie down and writing a fact-based report on her upcoming fourth wedding attempt. As Ike waits on yet another failure, he is gradually drawn closer and closer to Maggie and her quirky ways. Directed by Garry Marshall. With Joan Cusack, Hector Elizondo and Rita Wilson. Categories: Comedy, Romance. Year: 1999.

1999 in Runaway Bride
Malcom Crowe (Bruce Willis) is a psychologist whose terrifying experience with a troubled patient convinces him to devote his life to helping disturbed children. He focuses on Cole (Haley Joel Osment), a young boy who is able to see anguished dead people inhabiting the world. As Crowe tries to cure Cole's tormenting visions, he moves closer and closer to a terrifying truth about his own life. Directed by M. Night Shyamalan. With Toni Collette, Mischa Barton and Olivia Williams. Categories: Drama, Mystery, Thriller. Year: 1999.

1999 in The Sixth Sense
After a series of murders occur in the woods near Sleepy Hollow, constable Ichabod Crane (Johnny Depp) is called in to investigate. As he gathers evidence, the tale of the vengeful headless horseman becomes harder to refute with his practical logic. Crane's growing relationship with Katrina Van Tassel (Christina Ricci) compels him deeper into the woods, where he encounters the horror first hand. Directed by Tim Burton. With Miranda Richardson, Christopher Lee, Christopher Walken and Ian McDiarmid. Categories: Horror, Mystery, Thriller. Year: 1999.

1999 in Sleepy Hollow
With the galactic government weakened and the planet Naboo threatened by the Trade Federation, Jedi Knight Qui-Gon Jinn (Liam Neeson) and his apprentice Obi-Wan Kenobi (Ewan McGregor) set out to assist Queen Amidala (Natalie Portman) in settling the dispute, which places her people in great danger. But, when the Federation attacks, Qui-Gon and Obi-Wan must team up with a clumsy Gungan named Jar Jar Binks in order to save the Queen. And, as the evil Sith Lord Sidious plots to gain control of the Rebulic, Qui-Gon recognizes the strength of the force in Anakin Skywalker (Jake Lloyd), a young slave. Directed by George Lucas. With Samuel L. Jackson. Categories: Action, Adventure, Fantasy, Sci-Fi. Year: 1999.

1999 in Star Wars: Episode I - The Phantom Menace
Sean Penn stars as Emmet Ray, in this biopic of a fictional jazz guitarist. The arrogant Ray is considered the second-best jazz guitarist in the world, and he is obsessed with improving his reputation. Meanwhile, he falls in love with a mute woman (Samantha Morton) and gets involved with a high-society floozy (Uma Thurman). Directed by Woody Allen. Categories: Comedy, Music. Year: 1999.

1999 in Sweet and Lowdown
Tom Ripley (Matt Damon), a seemingly average and unassuming man, is hired by Herbert Greenleaf (James Rebhorn) to go to Italy and convince his playboy son Dickie (Jude Law) to return home. In Italy, Ripley is immediately embraced by Dickie and his beautiful ex-patriate girlfriend Marge (Gwyneth Paltrow), and experiences what it's like to live in luxury and have dear friends for the first time in his life. But, when Dickie tires of his interference, Tom cannot handle the rejection and goes to dangerous extremes to make Greenleaf's lifestyle his own. Directed by Anthony Minghella. With Cate Blanchett, Philip Seymour Hoffman, Jack Davenport and Philip Baker Hall. Categories: Crime, Drama, Thriller. Year: 1999.

1999 in The Talented Mr. Ripley
During the aftermath of the Gulf War, a group of American soldiers (George Clooney, Mark Wahlberg, Ice Cube and Spike Jonze) find a map that they believe will take them to a huge, hidden stockpile of gold. Determined to get their hands on the treasure, the men set out into the desert fully equipped to survive the harsh conditions and defend themselves as needed. But, when they discover people who desperately need their help, the soldiers rise to a heroic challenge that drastically changes their lives. Directed by David O. Russell. With Nora Dunn and Jamie Kennedy. Categories: Action, Adventure, Comedy, Drama, War. Year: 1999.

1999 in Three Kings
Gabriel (Christian Campbell) is a shy, gay office clerk who dreams of writing musical comedies. Tori Spelling plays his ditzy friend, Katherine, who wants to be a famous singer. When Gabriel meets Mark (John Paul Pitoc), a gorgeous go-go dancer, he falls head over heels in lust. Gabriel is shocked that Mark agrees to go home with him. But Katherine is there printing out her resume and won't leave. Where can these lovers go for a little privacy? Directed by Jim Fall. Categories: Comedy, Romance. Year: 1999.

1999 in Trick
In small town in Texas where high school football is king, the hopes and dreams of the entire community are on the line every Friday night. Head coach Bud Kilmer (Jon Voight) is trying to lead his West Canaan Coyotes to their 23rd division title when star quarterback Lance Harbor (Paul Walker) suffers a knee injury. Forced to turn to backup John Moxon (James Van Der Beek), the Coyotes come together and learn that there's more to being part of a team than just winning the games. Directed by Brian Robbins. With Amy Smart, Ron Lester, Scott Caan, Richard Lineback, Ali Larter and Thomas F. Duffy. Categories: Comedy, Drama, Sports. Year: 1999.

1999 in Varsity Blues
After their youngest daughter commits suicide, Mr. and Mrs. Lisbon (James Woods and Kathleen Turner) react by isolating her four remaining sisters from social interaction, especially with the opposite sex. When Lux (Kirsten Dunst), the most promiscuous sister, begins to rebel, Mr. and Mrs. Lisbon answer back by placing the girls under virtual house arrest. Although it's meant to protect them, the isolation only intensifies the obsessions of the girls' male classmates, and ultimately leads them to tragedy. Directed by Sofia Coppola. With Josh Hartnett, Scott Glenn, Danny DeVito, Hayden Christensen and Giovanni Ribisi. Categories: Drama, Mystery. Year: 1999.

1999 in The Virgin Suicides
When Elektra King's (Sophie Marceau) oil tycoon father is killed in a bombing at a British Secret Service headquarters, is assigned to protect her and track down her father's killers. As Bond pieces together information about the murder, he discovers that a series of oil pipeline sabotage attempts are part of a far more sinister plot, involving Elektra and the deadly terrorist Renard (Robert Carlyle). Directed by Michael Apted. With Denise Richards, Judi Dench and John Cleese. Categories: Action, Adventure, Thriller, James Bond. Year: 1999.

1999 in The World Is Not Enough