25 Best Romantic Movies on Amazon Prime Video for Valentine’s Day

Blake Lively attends 'The Age of Adaline' New York Premiere at the AMC Loews Lincoln Square 13 theater in New York City. �� LAN (Photo by Lars Niki/Corbis via Getty Images)
Blake Lively attends 'The Age of Adaline' New York Premiere at the AMC Loews Lincoln Square 13 theater in New York City. �� LAN (Photo by Lars Niki/Corbis via Getty Images) /
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2. She’s All That

Release Year: 1999

Written By: R. Lee Fleming, Jr., M. Night Shyamalan (uncredited)

Directed By: Robert Iscove

Starring: Freddie Prinze, Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O’Keefe, Kevin Pollak, Kieran Culkin, Elden Henson, Usher Raymond, Kimberly “Lil’ Kim” Jones, Anna Paquin

You might recall there was a moment in time when Freddie Prinze, Jr. had the market cornered when it came to romantic comedies targeted to Generation X teenagers. Summer Catch, Down To You, Boys and Girls, Head Over Heels—all of the classics. But it all began with She’s All That.

Prinze, Jr. stars as Zack Siler, who is naturally the most popular guy in school. On a bet with his friends, Zack vows to turn artistic wallflower Laney Boggs (Rachael Leigh Cook) into the prom queen. In the process of successfully making her over, Zack and Laney fall in love until the truth about the bet comes out.

Based on the George Bernard Shaw play Pygmalion and the film My Fair Lady, She’s All That surprised with its box office success and resulting popularity. The teen rom-com lives on as an enduring classic for the genre, and there’s even chatter of a remake. Throw it back to the good old days on Amazon Prime Video!