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
Four high school seniors make a pact to lose their virginity by prom night in this gross-out comedy. Jim (Jason Biggs) has awkward sex talks with his dad (Eugene Levy), Kevin (Thomas Ian Nicholas) already has a girlfriend (Tara Reid), Oz (Chris Klein) is a shy jock, and Finch (Eddie Kaye Thomas) is a skinny nerd. Stifler (Seann William Scott) is the quiet guy with the sexy mom, Shannon Elizabeth is the foreign-exchange student, and Natasha Lyonne is a girl who likes to joke. Directed by Chris Weitz. With Alyson Hannigan. 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