I did something very childish when Ryan Phillippe arrived at our shoot at the Gramercy Park Hotel's Rose Bar yesterday: I actually pretended not to notice him. I saw his flat brim cap and layered T-shirts out of the corner of my eye, Counting Crows' "Colorblind" started to play in my head, and I actively chose to stare straight ahead at the colorful potions and elixirs lining the wall and imagine what it might be like if this weren't an interview but rather a teenaged fantasy come to fruition. Because Ryan Phillippe—Sorry, Shosh, it is actually pronounced fill-uh-pee—was pretty much the first guy I ever loved. And, to his credit, he may have unwittingly affected my understanding of female sexuality. Don't worry, though. I told him as much, and his response was perfect: "Yeah Roger [Kumble], the writer slash director, really screwed up some kids, huh?"
To my pleasant surprise, there is no contrived celebrity bullshit with him—zero ego, preening, or pretense. He's just an eternally babyfaced hottie with sorta-dated arm tattoos, who does a killer Justin Timberlake impression, and fills out a pair of biker-style jeans with aplomb. (If you need convincing of his physical prowess, check out this very impressive video of him hopping up onto a box he swears is chest high.)
In anticipation of Sunday's premiere of his new ABC miniseries Secrets and Lies—a tense and unexpected crime drama about a family man (Phillippe) who is a detective's (Juliette Lewis) primary suspect in the murder of a little boy—the father of three and I sat down to discuss his many projects ("We live in a polymath potential society," he assures me), the benefits of growing older, depression, and finding closure with ex Reese Witherspoon. As for the drink order? Two rounds of sinisterly easy-to-drink sidecars. "The readers are going to love it," he says before banishing the drink's rock candy garnish to a cocktail napkin. "They're going to be like, 'Oh my god. He's so manly! He picked the strongest drink on the menu!'" Maybe it's the absinthe talking, but I can't argue with logic when it's accompanied by that stubble.
So, Ryan, you've got a new show, you just directed your first film, and now you're launching an e-commerce startup named Deedle. You're kind of all over the place!
I'm still acting, and I still love it, but I really want to try—and be willing to fail—in a bunch of different realms. I produced a documentary, a surf movie about the genocide in West Papua, that won a bunch of awards. And now, I'm really involved in helping to liberate a small country. That takes time away from acting, you know. And then I was writing and directing my first independent film; I'm directing my second this spring. I'm raising kids, as a single father, and I've got this startup. I get comments all the time on social media like, 'What ever happened to him?' or 'Where have you been?' Like, I'm doing stuff! It may not be stuff that you see, but I'm doing stuff.
As a newfound Philadelphian, I can't help but notice your Phillies cap there...
The 'P' stands for Phillippe, too. So it's like a double...
Nailed it.
Yeah, it works.
Growing up in Delaware, did you ever go out to bars on South Street?
Um, a little bit. 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. In the social sense, like, I started dating later in life; I didn't go out until later in life. I didn't do anything bad until I was older. I grew up pretty sheltered. I went to religious schools, so, all that kind of thing.
How's that worked out for you?
It's, you know. [Laughs] I'm my own man now.
It goes without saying, but I am a huge Cruel Intentions fan.
You know they're doing a Cruel Intentions musical? I heard it's really great. They're also remaking I Know What You Did Last Summer, which makes me feel like I'm about a hundred years old.
So I, along with millions of others, caught those Secrets and Lies spots during the Oscars on Sunday. Of course everyone wants to know if your character murdered this kid now...
What makes the series so interesting is that there's this guy who believes himself to be innocent, but because of the pressure and the scrutiny, he starts to behave like someone who is guilty. He starts to lose his mind a little bit.
When you and I were e-mailing before, you mentioned that you connected with the character because you yourself are 'quietly tortured at times.' What does that mean?
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.
Have you ever read any Joan Didion?
I have actually. I mean, I'm thankful in some ways to have that level of sensitivity, but it can also become a burden at times, you know?
If you could un-feel or reduce the receptors a little bit, would you?
Yes, absolutely. There's great value to it, but it can also ruin your fucking life. But, that being said, if it was a choice between being this way or being completely ignorant I'd prefer to suffer through the sadness than to be a complete moron with no feelings.
I feel you. I also think people who feel those acute emotions are also the funniest people.
Yeah.
And you seem pretty funny—even on social media!
Yeah, I am. I'm way funnier than people know me to be. And it's a dark humor, like a gallows humor. I think that's where, if you do carry any of that sadness or depression, your humor does tend to be a little darker than most people. And the greatest comedians do—trust me. I know so many of them. And they're depressed and they're dark and they have this incredible gift of humor to offer others and also, probably, therapeutically themselves.
Who's the funniest sad person you know?
I recently got to talk to one of my heroes for the first time: Louis C.K. He's my inspiration for so many things.
Not many people know this, but you played the first gay teen on television...
I was a pioneer!
Yes, you're a pioneer! You're super sensitive, I imagine you're a feminist…
I'm about to liberate this small country, trying to save the Rhinos…
You're a polymath!
Yeah! Yeah, I am! I love that word. You know, Pharrell loves that word.
Does he?
Yeah, he uses that word a lot. We live in a polymath potential society where you don't have to just do the same job. I say to my kids all the time, 'You can go on YouTube and learn anything.' If that had existed when I was growing up, when my brain was the sponge-like thing that theirs is...They can learn any instrument. They can learn a language. They can learn how to code! Like, why would you ever just be one thing your whole life? I mean, that's an antiquated way to go about.
What about negative feedback, though? You must get of thousands of comments on social media. What if someone's like, 'Deedle sounds lame'?
My skin is so thick at this point. I've been in the entertainment industry for 23 years so there's nothing anyone can say that I haven't heard or thought myself. You just keep movin', you know? That noise is so quiet at this stage of my life. What can people say that hasn't been said, and what does it really matter? Who am I trying to really prove anything to at this point in my life? Myself, my kids, my family….
You're 40, right? What changes between 30 and 40?
Metabolism, unfortunately. [Laughs]
You look so lean!
Well, that's because I train like a maniac. But you also start to care less about what other people think.
They say that about 30 too...
Well, I don't believe that about 30. I think 30 is tough. Like, nothing you do at 30 is like really special anymore. It's like, 'Oh yeah, you achieved this? Well, you should.' At 30 I definitely cared about what people thought. I was really concerned with perception and my place in the world, but now I'm just not.
Well, social media certainly doesn't help with that comparison impulse...
There is a novelty aspect to all this social media, right? I think there's going to be a burnout. I resisted all of it for a long time. The first year or so that I was on Instagram, I was religious about checking it when I woke up in the morning. But, I can feel it waning. I think I'm gonna have another drink.
Have you seen that Girls episode where they debate the pronunciation of your last name?
Yes.
Did you laugh as hard as I did?
I loved it so much. And then, a couple nights later, I was at the Howard Stern birthday party, and Lena Dunham was at my table, and she asked me if I was upset about it. I was like, 'What are you talking about? That's the coolest thing.' I'm a big supporter. I'm very feminist, man. I was raised by four women, my dad worked the 4 P.M. to midnight shift, so I was basically raised by four women. I'm so pro, pro female. There were some people laughing at Patricia Arquette's statement at the Oscars, but, in the state of California, women make 83 cents on the dollar compared to the man's full dollar. I mean over time, and over bodies, that adds up! It's not equal!
Okay, last question, what's one thing no one else knows about Cruel Intentions?
Well, everyone was always like in love with that Porsche I drive, but it was actually a plastic shell on the crappiest...It was not a real Porsche. It's basically a prop. But the girls don't care about that because I don't care about that either. But let me think, what else would people find interesting?
I like that Coldplay's playing right now while you think.
Yeah, it's, like, moving me. Well, here's something: sometimes I'll be filling up at a gas station and then, all of a sudden,"Bittersweet Symphony" will start playing. I'll turn around and there will be carload of girls laughing. It's a good song to be associated with though. I will say this, though. A few months ago when Catch Hell was coming out, I had to come to New York to do some press, and Reese was coming in to do some press, too, so she brought the kids. There was this cool moment where we took the kids for a walk in Central Park, the same place where we shot Cruel Intentions, and we were like, 'This is where Mom and I did this scene,' and the kids were like, 'Really?!'
Does that resonate? Do they get that?
Yeah, yeah, for sure they do! They haven't seen the movie, obviously, but we were like, 'You know, this is where we worked shortly after Mom and I got together. We stood on the exact bridge where Reese and I had a scene. It was a sweet, cool thing.
Talk about a "bittersweet symphony!"
I don't think that I would say that. I overly emotionalize a lot of things, but not something like that. Something like that I take as a full positive. Think about how many other families change directions and don't work out. So, to be able to share a moment, I consider a purely positive thing.
