10 Things I Hate About You - 1999
This film is packed to the brim with famous faces. Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt star in the romantic comedy that follows Kat Stratford and her quest to find a boyfriend. Her younger sister, Bianca, is not allowed to date until Kat does. This bizarre house rule is the catalyst for the entire movie.
Fans are still obsessed with Kat and Patrick's relationship, even today. They commonly grace 'top 10' lists in pop culture relationships. Watching this movie is absolutely a right of passage.