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"I can't tell you how old that makes me feel," Ryan Phillippe tells me, burying his head in his hands with a defeated laugh, when I bring up the forthcoming I Know What You Did Last Summer reboot. But time has been good to Phillippe, now 40. If you've seen Cruel Intentions—and you have, many times—then part of you still pines for Sebastian Valmont, the reformed bad boy Phillippe brought to life, next to whom all reformed bad boys have since been measured. Well, let me tell you, Phillippe measures up. The actor, and now director, hasn't changed too much since the late '90s—except he's added a tasteful sleeve of tattoos and listens to hip-hop you've never heard of.
After a stroll in Central Park with ex-wife Reese Witherspoon and kids Ava, 14, and Deacon, 10, Phillippe met me at the Four Seasons while in New York to promote his directorial debut, Catch Hell. A character-driven pulp thriller, the movie stars Phillippe as an actor (loosely himself), who's kidnapped and tortured in a dank cabin in Shreveport, Louisiana—where Phillippe actually filmed Straight A's with Anna Paquin last summer. (Yikes.)
Phillippe clearly had a lot of fun making the film, but he'll be the first to tell you that next time he's doing everything differently. And there will be a next time; in addition to shooting Secrets and Lies, an ABC drama co-staring Juliette Lewis, he's teamed up with Joe Gosset, who co-write Catch Hell, to write a couple more scripts that he intends to direct soon (one's about a giant in the NFL). But let's not skip ahead—first, we talk to Phillippe about the alligators he met in Louisiana.
You filmed in Shreveport last year. Was Catch Hell what you were worried might happen to you?
To some degree! As an actor you go to location, and you've only spoken to people on the phone. You've never seen anybody face to face. So I was in Shreveport, and I needed to take horseback riding lessons for the movie. These two guys pick me up at my hotel and drive me about 40 minutes away. I knew I was safe, but as we're driving into these woods, the plausibility of the whole scenario struck me. At home in LA, you might have video cameras and gates, and some people have guards. But you go on location, and when a van pulls up, you just blindly hop in.
Were those real alligators you got up close and personal with?
We did! Yeah, we had alligators on set—those are not CG. We didn't have the money for that [laughs]. We did it in 19 days, for under $2 million. There was a little bit of a guerrilla, "let's go for it and see what happens" mentality.
I noticed that Reagon Pearce, your character in Catch Hell, has the same publicist as you do in real life.
And my manager, David Schiffer, plays himself too. In no real disguised manner, I'm basically playing myself. Another thread to this movie was the attempt to do something like a reality-genre movie hybrid. I used myself, my career, and there are definitely references made to movies I've done under different titles. I just thought that was kind of fun. If I had had a choice I would've written this movie around Ryan Gosling and used his movies. But I wasn't going to get anybody like that [laughs].
What'd you learn as a first-time director?
There are a thousand things that I would do differently. The next one I'm not going to star in, firstly, because I would like to have the ability to focus on storytelling. It was really difficult at times to be chained up and going through this duress as the character and also trying to keep your eye on the movie.
You end on a surprisingly light note for such a dark movie.
Joe Gosset and I loved writing Stephen Grush's character, Junior. He became the soul of the movie. Even though our two characters meet in this really violent way, there's something about that guy that stays with you. I kind of wanted to let the viewer know that it was okay to like Junior.
Do your kids watch your movies?
The only one they've been able to watch is White Squall, and then Deacon couldn't handle it because I cry in the movie, so he had to turn it off. But Secrets and Lies, the 10-episode murder mystery I'm shooting now for ABC, is something they can probably actually watch.
Tell me about Secrets and Lies.
It's the most strenuous job I've ever had in my life, first of all, because what it will ultimately be is 10 hours of television, completely through my character's point of view. We're shooting in Wilmington, North Carolina, where I did I Know What You Did Last Summer, which is an odd, full-circle kind of thing. My character finds the body of a child and then becomes the prime suspect, and at the same time his marriage was already falling apart, so this is a guy who is losing everything. Juliette Lewis is awesome in it. People mostly think of as her wild characters, but here she's severe and serious.
You love your dark stuff.
[Laughs] I need to do a comedy after this. The next one I'm directing is a dark comedy within the vein of Raising Arizona. It's Fargo-ish.
Something your kids can watch!
Actually, these last couple years I've written three scripts with Joe, and for one of them, I set out to write my son's favorite movie, about a giant in the NFL—a guy who's 8 ft. 7 and can move like Bo Jackson.
What do you like to do with your kids?
Everything. Anything. Ava has started high school this year, and she's killing it in cross-country and debate. And my son's really into his flag football and golf. He's an incredible little golfer. We do a lot of outdoorsy sort of things like camping. And then there's video games.
How often do you listen to "Bittersweet Symphony?"
You know, the song always brings back fond memories. And I'll tell you something that has happened relatively recently: I'll be at a gas station, pumping gas, and I'll hear the "Din den dan, din den dan…" [singing], and I'll look over and see a car full of girls pointing [laughs]. If you have to be associated with a song, it's not a bad song to be associated with.
Your first acting job was playing TV's first gay teenager on One Life to Live. Did you have hesitations?
At the time I definitely did. Because I was 17. You're still unsure of who you really, not in regards to sexuality, but even just in terms of competence, your worldview, your experience. And I came from very religious schools. So when I took the job, I was ostracized. The reaction among my peers back home in that religious realm was really harsh. This is before Will & Grace. Thankfully things have changed.
So how'd you work up the courage to take the job?
It was my mom's favorite soap opera. My first job offer was to be on my mother's favorite show! How could I not? She got to come to the set and meet all the characters. And I do think I had an understanding very early on that actors play everything. As long as it's a worthwhile character, those other elements only enhance the potential.
You have some cool tattoos. Do they have stories?
This is a work in progress [pointing to left arm]. One is Ava's birthday, 9/9/99. I got this [alligator] after Catch Hell. That's a phoenix. The blue rose I got in Beijing. There's this whole mythology about the blue rose. Because the blue rose doesn't exist. In Chinese mythology, it's representative of unattainable beauty or perfection.
What's your next one going to be?
There's one I'm dying to get as soon as I get back to LA. It's going to be a Native arrow. I've been reading a lot about Native American history, and I want to do something that kind of connects me to that.
What do you do for fun?
My two primary areas of interest are comedy and hip-hop. Both speak a truth that other realms of the arts aren't allowed to. Those are the things I'm kind of obsessed with. I scour the Internet for the new, unreleased song. I have A&R people that call me up to ask what's going to break next. I'm a 40-year-old white guy, but I am a hip-hop aficionado! I'm friends with Hannibal Buress, the comedian, and we did this performance with Skrillex where he does this gibberish rap thing, and I was his hype man. It was this awesome confluence where I got to bring it all together.
Who are your favorite rappers?
I'm into a lot of the young guys who haven't really blown up yet, like Rockie Fresh and Casey Veggies and of course Bobby Shmurda. But I like the popular guys too. I'm a Drake fan and a [Lil'] Wayne fan — he's one of my top two rappers of all time.
You're dating Paulina Slagter now. What's your idea of a perfect date night?
Some incredible Japanese food, possibly a hip-hop performance and some good tequila, like really high-end Don Julio '42.
Romy Oltuski is a writer and editor based in New York. Her work appears in The New York Times, Forbes, Harper’s Bazaar, InStyle, and The Cut.
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