What did it take to be a heartthrob in the ‘90s? The qualifications were polarizing. On one hand, there’s Freddie Prinze Jr., the squeaky clean nice guy who will promise to be with you even after high school, even if he has to abandon his dreams and become a fisherman. And then there’s the messy-haired blonde bad boy-slash-jerk who drinks in your car and says things like, “Let’s dump the body.” That’s Ryan Phillippe, the late-‘90s bad boy who swept us off our feet, all whilst rocking a black turtleneck and wire-frame glasses.
As Barry William Cox in I Know What You Did Last Summer, he was a textbook jerk, loaded, ungrateful, and rude to women. It was his break out role, acting alongside the “it” squad of the MTV generation. But his most iconic performance was as Sebastian Valmont, twin and co-conspirator to Kathryn Merteuil (Sarah Michelle Gellar) in the modern classic Cruel Intentions, where they make a wager to deflower the new headmaster’s daughter.
It was one thing to be brooding and another to be actually to-the-core bad, and this was Philippe’s brand of sexy evil that drew in the fangirls. It was morally irresponsible to respond to his characters, but that was kind of the point.
After Jonathan Taylor Thomas, Andrew Keagan, Devon Sawa and all those wholesome kids teen magazines liked so much, came this pouty, snooty, scrawny kid who acted older than he actually was and dressed too tight for his time — the original Chuck Bass, vestibule of swag.
He did not quite rise to stardom, although he was married to A-list actress Reese Witherspoon. Philippe’s films are films we’ll remember forever (and watch over and over again) but they weren’t quite Romeo + Juliet. They’re just cool. That’s the beauty of the ‘90s — in between the American Beauty’s and the American History X’s were these easy-watching flicks that spoke to both the young and the once-young, no matter how outrageous their plots may be.
It was in 2015 that Hollywood started talking about Phillippe again, as he made his way back to the A-list via TV. Season one of ABC detective drama Secrets and Lies was his ticket; he plays Ben Crawford, the prime suspect in the death of a young boy in his neighborhood. While it wasn’t revolutionary it was a good start — it got people talking. Ryan Philippe is back, but is it his comeback? Not quite. Next came USA’s Shooter, executive produced by Mark Wahlberg who originally played Bob Lee Swagger in the 2007 film of the same name. In the TV series, Phillippe plays Swagger, a super sniper with 210 kills to his name, whose peaceful retirement of sorts is interrupted by a call to duty. As the film and Stephen Hunter novel Point of Impact (on which the show was based) goes, he ends up being wrongfully accused of a very serious crime.
Phillippe tries his best, but the story isn’t just as compelling as its contemporaries in political drama, such as Homeland, Designated Survivor, and House of Cards. As Bob Lee, he is sympathetic enough, but the plot just doesn’t dive into any real issue or make a stand. It’s just Swagger, hiding, plotting his revenge and coming across hurdles along the way, all the time. He isn’t written to be complex — in the film, the character is the same way. Not like Homeland’s Nicholas Brody, whose damage is revealed layer after layer with every episode. Phillippe does his best with what he’s given, creating a rough, Eastwood-esque persona that’s so far off from that twisted boy from Cruel Intentions that we can’t bring ourselves to believe it.
It is entirely possible that Phillippe has not been able to escape the shadow of his ‘90s semi-hugeness, entirely possible that it’s that too-good ending to the tune of Bittersweet Symphony that’s to blame. But longevity as an average actor is better than no longevity at all. Watching him, if only for the nostalgia and the fun of comparing how we remember him to who he is now, is not a terrible way to pass the time — or turn it a few decades back.
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The first season of Shooter is now streaming on Netflix.