The celebrity made his acting debut as a teenager and once mentioned that, even then, he looked much younger than his actual age. Because of his looks, he has also been mistaken for Justin Timberlake. Besides his appearance, he battled depression during his early years, something that stayed with him as he grew older.
The actor at the premiere of “Pleasantville,” 1981 | Source: Getty Images
From soap operas to big-screen hits, his life has played out in public. Now in his 50s, he continues to impress with his youthful looks and honesty about mental health, parenting, and life in Hollywood.
1990s
That striking appearance, however, had its drawbacks — especially during his early years in the 1990s when he was still trying to find his footing. He once said:
“I moved to New York when I was 17, and I looked like I was 12. So, you know, I wasn’t getting in anywhere. I looked like a literal child when I was a teenager. I was just pretty slow in that regard.”
Angelina Jolie and the actor at the premiere of “Playing by Heart,” 1998 | Source: Getty Images
While his boyish appearance brought challenges in his personal life, it didn’t stop him from making bold choices in front of the camera.
The celebrity attends the premiere of “Playing by Heart,” 1998 | Source: Getty Images
He got his start on the soap opera “One Life to Live” (1968), where he played Billy Douglas, the first gay teen character on daytime television in the U.S. The storyline tackled hard issues, including the fear of coming out and dealing with hateful reactions from others.
The actor at the premiere of “Cruel Intentions,” 1999 | Source: Getty Images
After that, he took on more TV roles before moving into film, appearing in “White Squall” (1996), “Nowhere” (1997), “I Know What You Did Last Summer” (1997), and “Cruel Intentions” (1999). As his film career picked up speed, his personal life also changed — he married his “Cruel Intentions” co-star Reese Witherspoon in 1999, and they welcomed their first child later that year.
The actor and Reese Witherspoon at the Vanity Fair Oscar Party on March 21, 1999, in Los Angeles, California. | Source: Getty Images
2000s
A few years later, the television star and the film producer expanded their family with the birth of their son, becoming a family of four.
The actor attends the Sixth Annual Blockbuster Entertainment Awards on May 9, 2000, in Los Angeles, California. | Source: Getty Images
The veteran actor later appeared in “Crash” (2005), “Flags of Our Fathers” (2006), and “Stop-Loss” (2008). After nine years, their marriage came to an end in 2008.
The celebrity attends the Hollywood premiere of “The Way of the Gun,” 2000 | Source: Getty Images
After their separation became public, media attention quickly turned his life upside down. At the height of the LA paparazzi craze, he found himself constantly followed. Hoping to escape the spotlight, he left the country to find some peace.
The actor during Hollywood premiere of “Little Nicky,” 2000 | Source: Getty Images
But quiet didn’t follow him. As soon as he arrived, strangers came up to him and asked, “‘Excuse me, are you Justin Timberlake?'” the celebrity recalled in an interview once.
The star poses at the Hollywood premiere of “Little Nicky” | Source: Getty Images
Despite the constant attention, his focus remained on his family. Speaking about life after the split, he once said that co-parenting, especially around the holidays, can be delicate.
The actor arrives at an after-party for the 58th Annual Golden Globe Awards on January 22, 2001, in Beverly Hills, California. | Source: Getty Images
Still, the star and Witherspoon, who once said he looked much better than Timberlake, ensured they stayed on the same page for the sake of their children.
The movie star attends a special screening of “Company Man” on March 5, 2001, in New York City. | Source: Getty Images
Even after parting ways, they found a rhythm that worked for their family. During one event in New York City, he explained how they manage Thanksgiving.
The actor arrives for a screening of “Legally Blonde” on July 7, 2001, in Southampton, New York. | Source: Getty Images
“As a divorced dad we trade off, so last year my kids and I went to my parents in Delaware, this year they will be with their mom and I am shooting a movie up in Toronto,” he shared. “I am going to fly down to Philly and just have a Thanksgiving with my parents and the kids get to be with Reese.”
The actor at the premiere of “Legally Blonde,” 2001 | Source: Getty Images
The Delaware native described their approach to parenting with care, noting that divorced parents, like any parent, must learn not to put themselves first.
The actor pictured on January 1, 2002 | Source: Getty Images
He emphasized the importance of letting the children have their own experience, rather than focusing on personal time, and shared that he and his former wife had managed that well.
The actor attends the premiere of “Vanity Fair” at the 61St Venice Film Festival on September 5, 2004 | Source: Getty Images
The father of two also acknowledged that the Academy Award-winning actress maintained a healthy attitude toward how they handled things.
The actor attends AFI Fest 2005 Opening Night Gala Presents “Walk the Line” Los Angeles premiere | Source: Getty Images
While their co-parenting arrangement remained steady, the actor behind it all, Ryan Phillippe, quietly faced battles that were far more personal. He once opened up about his longtime struggle:
“You know, depression has been a huge obstacle for me ever since I was a child. As you get older I think it decreases some, but I’m just innately kind of a sad person. I’m empathetic, and I take on the feelings of others and transpose myself into the position of others.”
Ryan Phillippe at the New York City premiere of “Walk the Line,” 2005 | Source: Getty Images
Phillippe explained that humor, especially the dark kind, had always been part of him. He believed he was much funnier than people realized, pointing out that his humor leaned toward gallows humor. According to him, those who carry sadness or depression often develop a darker sense of humor.
Ryan Phillippe spotted on February 26, 2006, in Los Angeles, California. | Source: Getty Images
The movie star noted that many of the greatest comedians he knew shared this trait — they were often depressed and carried a darkness within, yet had a unique ability to make others laugh, which also served as a form of healing for themselves.
Ryan Phillippe talks at the Four Seasons Hotel on October 7, 2006, in Los Angeles, California. | Source: Getty Images
That mix of honesty and humor has stayed with him throughout his career, even as time continues to move forward. Now more than 30 years into show business, Phillippe continues to work steadily.
Ryan Phillippe visits MuchOnDemand to promote his new movie “Stop Loss” on February 25, 2008, in Toronto, Canada. | Source: Getty Images
When he turned 47, he joked about how his appearance hadn’t changed much, but he no longer felt like the fresh face he once was:
“I still think of myself as relatively young and I still look relatively young but I am not, clearly.”
Ryan Phillippe arrives at the Vanity Fair Oscar Party on February 22, 2009, in West Hollywood, California. | Source: Getty Images
2010s
Even as he continues working and embracing the passage of time with humor, his youthful appearance brings its own set of complications. Phillippe once pointed out in a separate interview that looking much younger than his age isn’t always a perk. “I still get carded,” he said in his 40s.
Ryan Phillippe arrives at the premiere of “The Lincoln Lawyer,” 2011 | Source: Getty Images
His youthful appearance has led to awkward moments, especially when he’s with his daughter, who was 15 then. Strangers have confused him for her older brother, a mix-up that makes her uncomfortable. “It creeps her out,” he admitted, noting that some of her friends have even teased her about including him in games like spin the bottle during their sleepovers.
Ryan Phillippe attends the 28th Santa Barbara Film Festival “Isolated” premiere held at Lobero Theatre on January 30, 2013, in Santa Barbara, California. | Source: Getty Images
The confusion around his age may bring laughs or awkward moments, but staying youthful isn’t something he leaves to chance. The “Shooter” star credits his lasting looks to family genes and consistent effort.
Ryan Phillippe attends SNL 40th Anniversary Celebration on February 15, 2015, in New York City. | Source: Getty Images
He once said his mother also “still looks young,” and explained that taking care of his body helps more than just his appearance. Phillippe believes that a healthy lifestyle can ease the challenges of getting older.
Ryan Phillippe leaves the “Good Morning America” taping at the ABC Times Square Studios on July 10, 2017, in New York City. | Source: Getty Images
“If you eat right and exercise, it makes aging that much less disturbing, depressing and difficult,” he noted. Along with staying active and eating well, he relies on meditation to manage long-standing mood issues. And when it comes to looking after his skin, he never misses a step.
Ryan Phillippe attends the NBCUniversal Upfront presentation on May 14, 2018, in New York City. | Source: Getty Images
2020s
Sticking to his wellness habits clearly pays off, as his appearance continues to draw attention even at 50. In one Instagram post, Phillippe shared a mirror selfie that quickly caught the eye of his followers.
In the photo, the Hollywood star took a mirror selfie wearing a sleeveless white shirt, highlighting his toned arms and tattooed left arm. He pairs the look with sunglasses, bracelets, and a crossbody strap. His hair is tousled, and earbuds hang from his ears, giving off a relaxed, youthful vibe.
