For millennials with a TV, a DVD player and even a mild tolerance for teen drama in the late ’90s, Ryan Phillippe was unavoidable. He was the brooding heartthrob of Cruel Intentions, the doomed mischief-maker in I Know What You Did Last Summer — and, depending on your household rules, possibly the reason you got grounded for watching something you were absolutely too young to see. (Speaking from experience.)
So when we meet over Zoom for Yahoo’s interview series Off the Cuff, it makes sense that we first bond over teenage rebellion via movies.
“I think we all have one of those moments where we snuck and saw something we weren’t supposed to,” he says, smiling. “Mine that jumps out is Eddie Murphy: Raw. We snuck down into my friend’s basement and somehow got a copy of that.”
That shared nostalgia is a fitting entry point for an actor whose career has unfolded alongside an entire generation of moviegoers.
These days, at 51, Phillippe’s screen persona has evolved. The teen at the center of chaos has become the dad trying to outrun it, a natural progression for an actor whose audience has quite literally grown up alongside him. His latest project is an ambitious double-header: two thrillers — One Mile: Chapter One and One Mile: Chapter Two, both out now — that together tell one continuous story. He plays a father pushed to the limit when a trip meant to reconnect with his teenage daughter turns into a desperate fight for survival.
“There’s an element of familiarity. I have a teenage daughter,” he explains. Phillippe shares daughter Ava, 26, and son Deacon, 22, with ex-wife Reese Witherspoon. He’s also father to Kai, 14, with ex-girlfriend Alexis Knapp. “There are challenges at every stage when you’re a parent.”
That perspective feels earned. When Phillippe’s massive fame arrived in the late ’90s, it came fast and without much of a roadmap — a whirlwind stretch of heartthrob status and tabloid attention just as his career was taking off. At the time, he was in a serious relationship with Witherspoon, who he says helped steady the moment. “So that kind of kept me grounded throughout that.”
Asked what he’d tell his younger self now, his answer doubles as a quiet thesis for this next chapter. “Be true to yourself,” he says. “You will make mistakes, you will go through difficulties, but stay true to yourself, know who you are.”
It’s advice shaped by decades in the spotlight, personal highs and lows, and a career that’s been steadily recalibrated rather than reinvented. As he puts it, he’s most proud of the growth that isn’t always visible onscreen. “I feel like I’ve found some strength over the course of my life that maybe wasn’t there in the beginning.”
Here, Phillippe opens up about growing up on-camera, embracing his dad era and what still challenges him after three decades in Hollywood.
Audiences have grown up with you, from playing teens at the center of turmoil to now playing a father willing to do anything to save his daughter. What does stepping into that role feel like at this stage of your life and career?
I currently have a teenage daughter, and my other daughter is out of her teens, so there are things I definitely relate to. There are challenges when your kids are teenagers. I mean, there are challenges at every stage, in one way or another. But what appealed to me was that [my character] Danny had some regret and some guilt related to the fact that he wasn’t as much in her life as he would have liked to have been.
Danny is a guy who stayed in the military too long and missed out on a lot of her formative years. And so when he’s given this opportunity to spend time with his daughter on this trip, his hope is that there is a chance to reconnect and maybe make up for some lost time. So thematically and emotionally, I love that that’s the heart of our stories.
You’re playing a former special forces operative. How did you train, and does it feel different at 51 than it did in your 20s?
I’ve been in quite a few military projects over the course of my career: Shooter, Flags of Our Fathers, Stop-Loss. I’ve had a fair amount of training with various branches of the military. I’ve trained with Navy SEALs, Marines and the Army. I also come from a very military family. So a little bit of that is in my blood.
But yeah, it was a lot easier in my 20s, 30s, even 40s to take on. I’ve always been the type who wants to do all of his own stunts. When I did three seasons of the series Shooter, I think I only had a stunt double one time. That was a very action-intensive show.
Now, there are times when I’m willing to allow the stunt guy to do something. So I will step aside here and there begrudgingly, but less begrudgingly now that I’m the age that I am, because if you do get the inevitable bumps and bruises and scrapes and minor injuries, they don’t go away quite as quickly as they used to.
It’s getting more and more difficult as I get older to recover from the action, but I do enjoy it. I enjoy the challenge of it.
What does your health and wellness routine look like these days?
I’m someone who has studied fitness, nutrition and supplementation for decades now. Ever since I started working with a trainer in my early 20s, I’ve been pretty faithful to a regimen. I’ll work out five, sometimes six days a week, at least an hour a day. I’m really careful about what I eat.
I think we’re in an era where you get too much information on Instagram. You’ve got this health expert and that health expert telling you you need to buy this or take this. Some of it’s contradictory, and it can be really confusing in the end. I study it.
The core of anyone’s health and fitness journey has to be diet and exercise. For me, movement is incredibly important. It helps us age. We’re all going to age, but you’d rather age incrementally rather than just fall off a cliff.
Looking back at your early career, you took a risk playing the first openly gay teenager on daytime television. Do you see that as a defining moment in shaping the kind of actor and person you wanted to be?
In some ways, yes. Back then, that was a big deal. That was before Will & Grace or The Ellen Show, where those stories were mainstream. I did that when I was 17; there was a little bit of fear involved in 1992 about that, just coming into my own adolescence.
But it was really profound, the effect that it had on me emotionally and some of the fan mail that I would get from kids saying they had never seen a representation of who they were or someone like them before. Even from parents who found that character to be a bridge to relate to their child. It had a tremendous impact.
I’ve always been an empathetic and really sensitive person. So it kind of makes sense that I would start my career off with something that had that kind of meaning behind it.
You then became one of the defining leading men of the late ’90s and early 2000s. What was that heartthrob era like for you?
That was unexpected because I’d never seen myself that way. But then some audience would have a reaction to you that can be kind of heady. But also around that time, I was already in a relationship with [Reese Witherspoon], who became my wife and mother to two of my children.
I think that maybe if I had been a single man, it may have been more of a distraction, but it wasn’t. But it’s certainly an interesting thing to go through and navigate.
I still feel like I’m personally evolving and trying to get better as a father, as a son, as a friend, as a person in general.
Is there a project you loved that you feel didn’t get enough credit for?
Flags of Our Fathers with Clint Eastwood. … That was really important to me, having had both my grandfathers fight in World War II. That was a really important film for me. It got a good response. It didn’t do quite as well at the box office as we had hoped, but that’s going to happen sometimes. There are so many factors that go into whether something succeeds to that end or not.
But I think the important thing is, when you go into a project with the right intent, the right motives, and you give it all that you can, your heart and soul, then sometimes it doesn’t matter so much how it’s received, in a way, because you feel validated for your work and the reasons for doing that.
How do you define success for yourself at this stage in your career?
I still feel like I’m personally evolving and trying to get better as a father, as a son, as a friend, as a person in general. So I feel like that development should never really end. I’m always kind of trying to work on who I am and how I inhabit the world, how I influence or affect other people.
And I think success is something that is not unattainable, but it’s something that you’re always striving for, even once you have achieved [it]. I think that the moment we stop learning and we stop improving, part of us starts to die. So I’m always trying to be engaged in how I can get better. How can I be better?
This interview has been edited for length and clarity.
