If I hopped into a hot tub time machine and went back to the year 1999, I'd find my younger self swooning over a certain rascally private school womanizer named Sebastian Valmont. Blonde and beautiful, a smooth-moving lothario, Sebastian was the bad boy who could get any poor girl he wanted – and yet, he fell tragically in love with the nicest girl in all of Manhattan. (And then he married her in real life! Kinda.) So was it any wonder that from that point on, I'd harbor a major movie crush on the curly-haired heartthrob at the center ofCruel Intentions?

To clarify, Ryan Phillippe may have sealed his place in my movie crushing heart with his turn in 1999's Cruel Intentions, but I should have seen it coming. He was, after all, one of many beautiful youngsters who starred in the tragic boys-on-a-boat drama White Squall a few years prior. (Rest assured, friends, that film's cast will get its own dedicated Movie Crush column one of these days.) In 1996, Scott Wolf was riding high on his "Party of Five" fame, but who could resist the baby-faced Phillippe as the emotionally damaged Gil? Poor, pretty Gil. What a waste!

In the years immediately following White Squall, Phillippe stayed on our radar. He died way too early in I Know What You Did Last Summer, starred in the disappointing disco drama 54, and frightened all of your parents in Greg Araki's Nowhere. But none of those films made half the impact on the swooning masses of teenage girls the world over as his turn in Roger Kumble's modern remake of the French novel Les Liaisons dangereuses.