There was a time when Ryan Phillippe was known more for being "Mr. Reese Witherspoon" than he was for being a noted actor. Phillippe wouldn’t mind us acknowledging this. He has made similar, candid observations about his career and personal life while working the publicity circuit for his latest film, and directorial debut, Catch Hell.

In the film, Phillippe plays a slightly distorted version of himself – a once-famous actor who’s seeking the next big break that will put him back in the conversation at the major studios. Catch Hell evolves into a kidnapping thriller, but there’s enough honesty and autobiographical detail in the script to make you wonder, "Yeah, what did happen to Ryan Phillippe after all of these years?" The dude was in a number of engaging films over the course of his career. And yet, he readily admits to The L.A. Times, "I’ve made 30-plus films over 20 years. And in my opinion, five of them are good."

Is he right? And if so, which five are the "good" ones on Ryan Phillippe’s resume. Let’s spitball a few educated guesses.

Flags of our Fathers
Flags of Our Fathers
Many would argue that the follow-up film, Letters from Iwo Jima, was the better of Clint Eastwood’s two World War II dramas released in 2006 (and they would be right). But from Phillippe’s own perspective, the opportunity to work with an icon like Eastwood on a pedigreed war-effort picture about a seminal moment of American history has to feel like a win. I’m willing to bet Ryan Phillippe’s proud that Flags of Our Fathers is part of his filmography.
Gosford Park
Gosford Park
Long before our nation’s Downton Abbey craze, Robert Altman gracefully weaved through the lives of British aristocrats and the servants who knew every inch of their daily existences. Again, Phillippe gets to study under a legend in Robert Altman, and call Helen Mirren, Maggie Smith and many others colleagues. Gosford Park earned multiple Oscar nominations, including Best Picture. It has to be a highlight for the 40-year-old Phillippe.
Crimson Tide
Crimson Tide
It doesn’t matter that Phillippe had a small part in Tony Scott’s harrowing submarine thriller. When the actor is combing over his past conquests and pointing out the movies that actually worked (and worked well), there’s no way he can overlook the expertly paced, energetically acted standoff act that dialed back on Tony Scott’s usual flourishes and kept the cameras focused on Denzel Washington and Gene Hackman. Never a bad idea.
Crash
Crash
Listen, I don’t care for Paul Haggis’ Crash. It’s manipulative, ham-fisted and overly melodramatic. But the people who like Crash ADORE it, and I’m quite sure Ryan Phillippe’s proud of the work that he did in the sprawling ensemble for this eventual Best Picture winner. Yep, Ryan Phillipps starred in a Best Picture winner. This wouldn’t be on my list, but it’s likely on his. Right?
Cruel Intentions
Cruel Intentions
You’re damn right Cruel Intentions makes this list. It’s easy to make forgettable, throwaway shlock in Hollywood. But it’s extremely difficult to make memorable shlock that purposefully pushes the envelope of good taste to get a rise out of an audience. Cruel Intentions didn’t put its young cast on the map. But it helped us see them in a different light, opening up doors for Phillippe, his eventual wife Reese Witherspoon, Sarah Michelle Gellar and Selma Blair.

It’s worth noting that Phillippe low-balls his own career, as this list easily could have included The Way of the Gun, Stop-Loss, 54, I Know What You Did Last Summer, White Squall, Igby Goes Down, The Lincoln Lawyer and, obviously, MacGruber.

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