Best Rom-Com movies of 1999

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 : Rhys Ifans, Julia Roberts, Hugh Grant, 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 : 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 : 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 : 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 : 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 : Steve Zahn, Maura Tierney, Ben Affleck, Sandra Bullock,
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 : Angelina Jolie, Cate Blanchett, John Cusack, Billy Bob Thornton,
Directors : Mike Newell,

A feud develops between two air traffic controllers: one cocky and determined while the other is restrained and laidback, which inevitably affects their lives.

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.

Actors : Michelle Williams, Clea DuVall, Brandt Wille, Natasha Lyonne,
Directors : Jamie Babbit,

A naive teenager is sent to rehab camp when her straitlaced parents and friends suspect her of being a lesbian.

Actors : Tommy Bone, Amy Smart, Shawn Hatosy, Alec Baldwin,
Directors : Michael Corrente,

After one too many run ins with the law, a punk teenager from a working class background is sent to prep school by his frustrated dad, and learns a thing or two.

Actors : Steve Zahn, Ally Walker, William H. Macy, Jeremy Northam,
Directors : Mark Illsley,

Two escaped convicts arrive in the town of Happy, Texas, where they are mistaken for a gay couple who is to host the town's Little Miss Fresh Squeezed beauty pageant. Enjoying the celebrity...

Actors : Ellen Barkin, Kirsten Dunst, Denise Richards, Allison Janney,
Directors : Michael Patrick Jann,

A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win.

Actors : Matthew Perry, Neve Campbell, Dylan McDermott, Oliver Platt,
Directors : Damon Santostefano,

A rich businessman's assumption that his new colleague is gay leads him to ask the man to keep an eye on his mistress. However, the man is not gay, and begins to fall for the woman himself.

Actors : Guillermo Díaz, Dave Chappelle, Ben Affleck, Casey Affleck,
Directors : Risa Bramon Garcia,

A collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses.

Actors : Sean Nelson, Richard T. Jones, Omar Epps, Elayn J. Taylor,
Directors : Rick Famuyiwa,

While dealing with a friend's cold feet on his wedding day, a writer reminisces about his youth with his best friends.