There's Something About Mary

Release 1998

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Director: Bobby Farrelly, Peter Farrelly
Writers: Ed Decter, John J. Strauss, Peter Farrelly, Bobby Farrelly
Stars: Cameron Diaz, Matt Dillon, Ben Stiller, Lee Evans, Chris Elliott
IMDB: http://www.imdb.com/title/tt0129387/

A man gets a chance to meet up with his dream girl from highschool, even though his date with her back then was a complete disaster.