Stop-Loss, which opens March 28, is the highly anticipated sophomore effort from Boys Don’t Cry writer-director Kimberly Peirce. If the film lives up to its pedigree, and audiences decide they’re finally ready to confront the realities of the Iraq war on the silver screen, it will probably go down in history as the film that made a bona fide star out of Step Up hottie Channing Tatum. People having been dying to see this guy in a good movie since he first danced into our hearts two years ago. If Stop-Loss is a hit, Tatum’s (preferably shirtless) image will appear across countless magazines proclaiming him the new “It” boy, while Paramount executives will be dreaming about the tanks of cash he’ll drive in when G.I. Joe hits theaters in 2009. Meanwhile, Ryan Phillippe, the actual leading man of Stop-Loss, will continue on his journey to becoming the handsomest has-been in Hollywood.

How did this happen? I’m sure many of you can remember the spring of 1999, when Phillippe was the bare-chested beefcake on those magazine covers. Then 25, Phillippe had grown quite a following of teen girls who’d swooned over him in films like 54, I Know What You Did Last Summer, and most notably, Cruel Intentions. Even the grown-ups seemed to think this kid had a real future ahead of him. And it didn’t hurt that he was romantically involved with his talented Cruel Intentions costar, Reese Witherspoon. Why, this young couple was poised to become the next Tom and Nicole!

But somehow, Cruel Intentions became the last time anyone would pay serious attention to Ryan Phillippe. It seemed like a new “It” boy (Heath Ledger) had been crowned by the time Phillippe had re-buttoned his shirt! Sadly, his personal life would also take a downturn when he and Witherspoon divorced in 2007.

Here’s how Phillippe lost it all:

1.) He let Jonathan Rhys Meyers steal his niche.
Apparently, there’s only room for one soulless pretty boy in this biz, and JRM is currently it. The social-climbing tennis coach in Match Point, and the haughty soldier in Vanity Fair were parts totally suited for the dead-inside sarcasm and perfect pout Phillipe won audiences over with in Cruel Intentions. In the case of Vanity Fair, Phillippe was even married to its leading lady! Why didn’t he chase after these roles?

2.) He gave his best performances in movies that no one saw or that no one noticed him in.
In 2002, Phillippe took his heartless rich-boy routine from Cruel Intentions and layered it with dramatic depth in the dark indie comedy Igby Goes Down. The film was well-received by critics, and Phillippe was joined by an all-star cast including Susan Sarandon, Jeff Goldblum, and Claire Danes. Unfortunately, the film didn’t get a wide release, and all the buzz surrounding it centered on Kieran Culkin’s breakthrough performance. He was similarly overshadowed in the prestigious ensembles of Crash and Gosford Park. And despite a solid performance in Flags of Our Fathers and his smartest, most mature work to date in Breach, Phillippe just couldn’t hit it big at the box office.

3.) He lost custody of the fans in the divorce.
In every celebrity break-up, there’s a winner and a loser (see Timberlake/Spears). Phillippe made the mistake of publicly admitting his jealousy over his Oscar-winning wife’s success. No woman is going to sympathize with a man who can’t be happy for his wife, no matter how handsome or talented he may be.

Hopefully, the nail really isn’t in the coffin of Ryan Phillipe’s career yet. Maybe people will see Stop-Loss and pay attention to more than just Channing Tatum’s biceps. But if this really is the end for Phillippe, at least we know he’s an actor who has always known how to go out in style.

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