Ryan Phillippe, 42, broke onto the Hollywood scene in the 1990s with a slew of provocative movie roles and a front-page romance with leading lady Reese Witherspoon. Ever since, the now-divorced dad of three has managed to keep himself in the headlines with a busy career and an even busier love life. Since Ryan's latest thriller, "Wish Upon," is set for release on July 14, let's take a look back at some nostalgia-inducing pictures of one of our favorite Hollywood hunks.
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How adorable was teenage Ryan Phillippe?! At just 18 years old, he got his small-screen start on the ABC daytime soap "One Life To Live" playing Billy Douglas. But Billy, whom Ryan portrayed in 1992 and 1993, wasn't just any old character: He was the first openly gay teen on a television series.
What does one do after making daytime television history as a teen? Ryan Phillippe went on to make a horror movie for the ages! In 1997, he starred alongside Sarah Michelle Gellar, Jennifer Love Hewitt and Freddie Prinze Jr. in the hit "I Know What You Did Last Summer." The movie became a teen cult classic and this promo pic of the foursome standing on an eerie dock remains forever ingrained in pop culture.
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The 1998 dramedy "Playing By Heart" flew under the radar despite its A-list cast. But Angelina Jolie and Ryan Phillippe as an on-screen couple was hard to forget — especially given the fiery red and electric-blue locks they sported for their roles. We hope this film still is framed in his house somewhere.
Ryan Phillippe and Breckin Meyer were shirtless more often than not in 1998's sexy film "54," which was set at a famous nightclub during the '70s disco era. We're grateful to Ryan for breaking out of his shell with this alluring role, mainly because of the hot, half-naked scenes he shared with co-stars Salma Hayek and Neve Campbell.
While hunk Ryan Phillippe was catching the attention of fangirls everywhere, there was one lady in particular who caught his eye. After reportedly meeting at Reese Witherspoon's 21st birthday party in 1997, Ryan started dating the young Hollywood starlet. About a year later, they were engaged. Their puppy love was front and center on red carpets after that, such as this one for an AIDS Project Los Angeles event in 1998.
Ryan Phillippe and Reese Witherspoon's off-screen chemistry translated to the big screen in 1999's "Cruel Intentions." Their seductive moments in the film solidified them as a couple in fans' eyes and encouraged the world's infatuation with their real-life hot romance.
Ryan Phillippe, Sarah Michelle Gellar, Selma Blair and Reese Witherspoon's intensely sexual gazes in this "Cruel Intentions" promo pic still sizzle nearly 20 years later. The titillating film, which followed the sexual coming of age of a group of prep-school students, made a serious mark on Ryan's career, establishing him as a provocative actor. His performance as Sebastian Valmont, along with that devilishly charming look in his eyes, is impossible to forget.
As husband and wife, Ryan Phillippe and Reese Witherspoon slowly emerged from their teenage careers and grew into an adult Hollywood power couple. They took on the roles of Mom and Dad when they welcomed daughter Ava Phillippe in 1999. Their evolution into maturity was evident as they stunned on the red carpet together at the 2002 Oscars.
Ryan Phillippe continued to evolve in his personal life and his career: One year after he and Reese Witherspoon welcomed son Deacon Phillippe in 2003, he starred in the ensemble drama "Crash," which won Best Picture at the 2005 Oscars. He continued his foray into more serious roles with the 2006 historical war film "Flags of Our Fathers," based on events from the 1945 Battle of Iwo Jima. This image of Ryan as Pharmacist's Mate Second Class John Bradley in the Clint Eastwood-directed movie leaves an indelible mark.
Though Ryan Phillippe's career was holding steady, his marriage was hanging on by a thread. In January 2006, he and Reese Witherspoon appeared loved-up at a Golden Globes afterparty where they were celebrating Reese's Best Actress win for "Walk the Line." But looks were deceiving: Just nine months later, they announced their split. "I think more of the problem was age," Ryan revealed on "Larry King Now" in 2015. "When we got together, we were so young,"
Cheers to Ryan Phillippe taking shots with Channing Tatum, Joseph Gordon-Levitt and Abbie Cornish! The actors starred together in 2008's war film "Stop-Loss," which followed the lives of four young soldiers psychologically affected by the war in Iraq. In between filming scenes for the heavy flick, Ryan fell for co-star Abbie.
Abbie Cornish was Ryan Phillippe's first major girlfriend after his split from Reese Witherspoon. The couple coasted along drama-free (well, aside from whispers that she was the catalyst for his divorce) for a few years and looked quite content in this January 2010 photo from a Hollywood event honoring Abbie — but they called it quits soon after. That same year, Ryan quickly moved on with model Alexis Knapp, though their relationship only ended up lasting a few months. Soon after parting ways, the exes learned that they were expecting and welcomed daughter Kailani Phillippe-Knapp in 2011.
What a hunky sight! We wish 2011's "The Lincoln Lawyer" could be re-released just so that Ryan Phillippe and Matthew McConaughey would have to do photocalls side-by-side again. Though the crime drama was a blockbuster success, Ryan's next few movies were flops, including a straight-to-DVD heist flick called "Setup."
Following Ryan Phillippe's breakups with Abbie Cornish and Alexis Knapp, he became quite the eligible bachelor. In 2011, he was rumored to be getting cozy with "Dear John" actress Amanda Seyfried, though a romance was never actually confirmed.
And the Dad of the Year Awards goes to… Regardless of Ryan Phillippe's rocky love life, he's always remained a great father. This 2012 image of the hot dad tying son Deacon Phillippe's cleat laces before a soccer game is pretty adorable. Over the years, Ryan has been frequently photographed on the sidelines of his boy's games.
Ryan Phillippe's babies seemed to have grown up so fast! In this 2013 image, daughter Ava Phillippe is already almost as tall as her pops! We love Ryan's casual hangouts with his kids, like this one when they were snapped grabbing lunch in Malibu.
In between daddy duty and making career power moves like directing his first film, 2012's "Catch Hell," Ryan Phillippe found love again with law school student Paulina Slagter. The sexy couple made for some pretty fiery photo ops together, including this image of the pair at a New Year's Eve bash in Miami in 2013.
Paulina Slagter became a pretty permanent fixture in Ryan Phillippe's life, even blending in amicably with ex-wife Reese Witherspoon and their kiddos. In 2013, the whole bunch, including Reese's second husband, agent Jim Toth, was seen making nice as they cheered on Deacon Phillippe during a soccer game in Los Angeles. Ryan even took it to the next level when he proposed to Paulina in 2015, but the couple split the following year.
It seems as if the older Ryan Phillippe gets, the more buff he becomes — and we're definitely not complaining. Take as long as you'd like to stare at this shot of the hunk going for a shirtless jog in Los Angeles in 2015. It's crystal clear why he's been on the cover of magazines like Men's Health and Men's Fitness.
Ryan Phillippe looks just as hot shirtless as he does dressed as a cop in a cowboy hat. We're all about his latest move back to the small screen in the 2017 series "Shooter." While this recent pic isn't nostalgic just yet, we look forward to coming back and swooning over it in a few years.