25 of the most swoon-worthy romance movies of all time

Heath Ledger and Julia Stiles at swing in a scene from the film '10 Things I Hate About You', 1999. (Photo by Buena Vista/Getty Images)
Heath Ledger and Julia Stiles at swing in a scene from the film '10 Things I Hate About You', 1999. (Photo by Buena Vista/Getty Images) /
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10 Things I Hate About You

This is the moment the world fell in love with Heath Ledger, and it’s pretty damn easy to see why. This film, based on William Shakespeare’s Taming of the Shrew, is the modern take on an old story.

10 Things I Hate About You is the story of  Kat Stratford (Julia Stiles) who is beautiful, smart and we’re told she’s the worst, forcing pretty much everyone to run in the other direction when she comes near. Unfortunately for her younger sister, Bianca (Larisa Oleynik), house rules say that she can’t date until Kat does, so she (and her male admirers) pay Patrick Verona (Heath Ledger) to take her sister out so that Bianca may enjoy the fruits of a high school romance. As romances go, they end up actually liking each other, until Kat finds out that Patrick is being paid to take her out. Now Patrick must prove he’s really into Kat while she turns her attitude way up. 

Not only is this one of Ledger’s first big roles, you’ll also see Joseph Gordon-Levitt before he grew into the hunk that we know him to be today, and Andrew Keegan too!

Be prepared for a big song and dance number (not cheesy though, I promise it’s really cute), some crude ’90s humor and some fashion that should be burned on sight, otherwise this is a top-notch rom-com that’s remained a fan favorite nearly 20 years later.

Fun Fact: Heath Ledger beat out Josh Hartnett and Ashton Kutcher for the role of Patrick, it would be his first American movie.

Release date: March 31, 1999