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.
Transposing the novel's aristocratic French setting to a modern-day New York private school, Cruel Intentions starred Phillippe as Sebastian, a bored rich kid engaged in games of sex and manipulation with his step-sister, Catherine (Sarah Michelle Gellar). When Sebastian unwittingly falls for the object of their latest wager (Reese Witherspoon), his entire world view changes and the callous seducer finds himself standing at the top of an escalator in the subway waiting to declare his love while Adam Duritz of Counting Crows sings his inner thoughts in the background! Le sigh. I dare any teenage girl circa 1999 to deny the power of that single moment.

See? You cannot.

In hindsight, Sebastian's appeal was that of the classic bad boy-gone-straight, the hunky womanizer that would drop every single vice in a heartbeat for the right woman. (Wish fulfillment? Absolutely.) He was also a sexually sophisticated aggressor who'd probably done it all (and to everyone in town), but Reese Witherspoon's goody two-shoes Annette – a symbol of purity and virginity – was the one who captured his heart. Well, she was mostly pure and virginal. She only gave it up once he admitted his undying love!

The story, in all of its tragedy and depravity, was nothing new. In fact, Cruel Intentions followed its 18th century source novel pretty closely in terms of plot. And for the MTV generation, the idea of watching Phillippe mack on Witherspoon was a heckuva lot more enticing than watching old-timer John Malkovich seduce Michelle Pfeiffer in Dangerous Liaisons. And salacious as it was, Cruel Intentions was the rare mainstream teen flick that recognized just how hormonal (and cruel) teenagers could be.

Cruel Intentions, which became a box office hit, also marked a turn in Phillippe's career. It was as if after playing the ultimate high school bad boy, Phillippe was ready to move on to adult roles and leave his teen idol years behind. He next appeared as a doomed criminal in Christopher McQuarrie's The Way of the Gun, an underappreciated neo-Western that emerged as a cult film. The tech-thriller Antitrust, however, disappointed. But a run of subsequent prestige films yielded acclaim, as Phillippe turned up in Robert Altman's Oscar picGosford Park, Paul Haggis's Best Picture winner Crash, and Clint Eastwood's Flags of Our Fathers.

Last week at SXSW I happened to catch Phillippe's next big flick, the action comedy MacGruber, in which he makes his broad comedy debut playing the straight man to Will Forte's titular "Saturday Night Live" character. (Phillippe is set to host "SNL" on April 17.) I'm happy to report that the Phillippe faithful should be delighted on many counts; he's as pretty as ever, he hangs with his comic co-stars like a pro, and as evidenced by one unforgettable scene involving celery, he's got a solid sense of humor about his career longevity (beyond that, my lips are sealed). Nabbing Phillippe on the red carpet to talk about MacGruber, I was surprised when he brought up the film that made him the object of so many teen crushes back in the day.

"Even though the movie was made over ten years ago, still every day somebody comes up and tells me how much they love that movie," he said. "People who were not even really of age when it came out still see it. And to be a part of one of those seminal teen movies is actually really cool."

Does he still feel like a teen idol deep down inside, I asked?

"Not really – I'm too old for that," he replied.

I wouldn't be so sure. (Cue "Bittersweet Symphony.")