Best Romance movies of 1999

Actors : Kevin Spacey, Thora Birch, Annette Bening, Wes Bentley,
Directors : Sam Mendes,

A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.

Actors : Reese Witherspoon, Matthew Broderick, Chris Klein, Jessica Campbell,
Directors : Alexander Payne,

A high school teacher's personal life becomes complicated as he works with students during the school elections, particularly with an obsessive overachiever determined to become student body president.

Actors : Josh Hartnett, James Woods, Kirsten Dunst, Kathleen Turner,
Directors : Sofia Coppola,

A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents in suburban Detroit in the mid-1970s.

Actors : Tobey Maguire, Delroy Lindo, Michael Caine, Charlize Theron,
Directors : Lasse Hallström,

A compassionate young man, raised in an orphanage and trained to be a doctor there, decides to leave to see the world.

Actors : Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Julia Stiles,
Directors : Gil Junger,

A pretty, popular teenager can't go out on a date until her ill-tempered older sister does.

Actors : Rhys Ifans, Hugh Grant, Julia Roberts, Richard McCabe,
Directors : Roger Michell,

The life of a simple bookshop owner changes when he meets the most famous film star in the world.

Actors : Reese Witherspoon, Sarah Michelle Gellar, Ryan Phillippe, Selma Blair,
Directors : Roger Kumble,

Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.

Actors : Michael Vartan, David Arquette, Molly Shannon, Drew Barrymore,
Directors : Raja Gosnell,

A newspaper reporter enrolls in high school as part of research for a story.

Actors : Jennifer Esposito, Mira Sorvino, Adrien Brody, John Leguizamo,
Directors : Spike Lee,

Spike Lee's take on the "Son of Sam" murders in New York City during the summer of 1977 centering on the residents of an Italian-American Northeast Bronx neighborhood who live in fear and distrust of one another.

Actors : Sean Connery, Catherine Zeta-Jones, Will Patton, Ving Rhames,
Directors : Jon Amiel,

An insurance agent is sent by her employer to track down and help capture an art thief.

Actors : Sissy Spacek, Brendan Fraser, Alicia Silverstone, Christopher Walken,
Directors : Hugh Wilson,

A naive man comes out into the world after spending 35 years in a nuclear fallout shelter.

Actors : Rachael Leigh Cook, Matthew Lillard, Paul Walker, Freddie Prinze Jr.,
Directors : Robert Iscove,

A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.

Actors : Hector Elizondo, Julia Roberts, Joan Cusack, Richard Gere,
Directors : Garry Marshall,

A reporter is assigned to write a story about a woman who has left a string of fiances at the altar.

Actors : John C. Reilly, Jena Malone, Kelly Preston, Kevin Costner,
Directors : Sam Raimi,

A washed up pitcher flashes through his career.

Actors : Jeanne Tripplehorn, Hugh Grant, Burt Young, James Caan,
Directors : Kelly Makin,

An English auctioneer proposes to the daughter of a mafia kingpin, only to realize that certain "favors" would be asked of him.

Actors : Paul Walker, Ron Lester, Jon Voight, James Van Der Beek,
Directors : Brian Robbins,

A back-up quarterback is chosen to lead a Texas football team to victory after the star quarterback is injured.

Actors : Tobey Maguire, Jewel Kilcher, Jeremy W. Auman, Skeet Ulrich,
Directors : Ang Lee,

Jake Roedel and Jack Bull Chiles are friends in Missouri when the Civil War starts. Women and Blacks have few rights. Jack Bull's dad is killed by Union soldiers, so the young men join the ...

Actors : Steve Zahn, Maura Tierney, Sandra Bullock, Ben Affleck,
Directors : Bronwen Hughes,

A soon-to-be-married man encounters an exciting stranger after his plane suffers an accident on takeoff.

Actors : Eddie Griffin, Rob Schneider, Arija Bareikis, William Forsythe,
Directors : Mike Mitchell,

An average aquarium cleaner house-sits for a gigolo, only to be forced to become one himself.

Actors : Colleen Rennison, Jake Sandvig, Bruce Willis, Michelle Pfeiffer,
Directors : Rob Reiner,

Ben and Katie Jordan are a married couple who go through hard times in fifteen years of marriage.