Top 19 Romance Movies Hits from 1999

Four teenage boys enter a pact to lose their virginity by prom night. More about American Pie / IMDB / YouTube

A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat. Learn about 10 Things I Hate About You / IMDB / YouTube

A set of circumstances makes Anna Scott, a famous actress, fall in love with William Thacker, owner of a bookstore in Notting Hill. But the paparazzi's fascination with her complicates their bond. See more about Notting Hill / IMDB / YouTube

The world's greatest-ever playwright, William Shakespeare, is young, out of ideas, and short of cash, but meets his ideal woman and is inspired to write one of his most famous plays. See more about Shakespeare in Love / IMDB / YouTube

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. Info on Cruel Intentions / IMDB / YouTube

A teenager at Rushmore Academy falls for a much older teacher and befriends a middle-aged industrialist. Later, he finds out that his love interest and his friend are having an affair, which prompts him to begin a vendetta. Look into Rushmore / IMDB / YouTube

The life and times of Andrew, a robot purchased as a household appliance programmed to perform menial tasks. As Andrew begins to experience emotions and creative thought, the Martin family soon discovers they don't have an ordinary robot. Look into Bicentennial Man / IMDB / YouTube

Insurance investigator Virginia Baker deems that the thief Robert MacDougal has robbed a Rembrandt painting. To retrieve the painting, she poses as an art thief, cooperating with him in criminal acts. Learn about Entrapment / IMDB / YouTube

A high school teacher meets his match in an over-achieving student politician. Explore Election / IMDB / YouTube

When Zack's famous girlfriend, Taylor, cheats on him with another boy and parts ways with him, he makes a bet with his friends to turn a socially inept Laney into their high school's next prom queen. Explore She's All That / IMDB / YouTube

For his latest column in USA Today, Ike Graham writes about Maggie, who always leaves all her fiances standing at the altar. He is fired as she complains to the newspaper for inaccuracies in her story. Explore Runaway Bride / IMDB / YouTube

A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective. Find out about The Thomas Crown Affair / IMDB / YouTube

A newspaper reporter enrolls in high school as part of research for a story. Learn about Never Been Kissed / IMDB / YouTube

An average aquarium cleaner house-sits for a gigolo, only to be forced to become one himself. Learn about Deuce Bigalow: Male Gigolo / IMDB / YouTube

A naive man comes out into the world after spending 35 years in a nuclear fallout shelter. Get info on Blast from the Past / IMDB / YouTube

A back-up quarterback is chosen to lead a Texas football team to victory after the star quarterback is injured. Details on Varsity Blues / IMDB / YouTube

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. Details on Summer of Sam / IMDB / YouTube

A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win. Look into Drop Dead Gorgeous / IMDB / YouTube

A woman discovers a tragic love letter in a bottle on a beach, and is determined to track down its author. Get info on Message in a Bottle / IMDB / YouTube