PLAYBOY: Is success what you thought it would be?
SHEPARD: Oh God no, but it’s impossible to know until you’ve had success that it doesn’t alter your daily struggles. When I was a struggling Groundling, I thought if I had the life I have now I wouldn’t have to brush my teeth anymore and could eat cupcakes all day. In fact, I have to do the same shit I’ve always had to do to not feel miserable, which is work out, journal, eat well, do something for somebody other than myself at some point every day—even if it’s just the dogs, those little fuckers.
PLAYBOY: So was that really you driving like an outlaw in Hit & Run?
SHEPARD: One hundred percent. I’m from Detroit, and my life has been driving cars. In high school it was drag racing. Then I worked for GM because my mother had a company that put on big car shows for journalists. We’d rent out Michigan International Speedway, and I got tons and tons of seat time in these crazy cars that a 16-year-old should never be allowed to drive. I fucking love cars, and I’ve wanted to do a car-chase movie all my life.
PLAYBOY: Correct us again, but it also appears that your superhot, superfamous co-star and fiancée, Kristen Bell, was actually buckled in alongside you.
SHEPARD: For every bit of it. Naturally the producer had booked a stunt double, but Kristen said to me, “No. If you’re driving through a barn and jumping other cars, I need to be in there with you. We’re going to go out together.”
PLAYBOY: She sounds like a keeper.
SHEPARD: Kristen’s a good girl. She grew up very Christian, went straight to college, did great in school and started work immediately. She’s charitable and philanthropic and rescues dogs. So when we met, our backgrounds were opposites. All the things I’d done were terrifying to her, and she had a hard time believing I would ever be able to stay married and monogamous and a father and all those things. For the first year and a half we were together that was what we battled over almost weekly.
PLAYBOY: How terrifying were you exactly?
SHEPARD: It’s so weird when you turn 18 and are released into the world and then just start piling on terrible habits. From 18 to 29 I was a heavy smoker, heavy drinker, drug addict, terrible eater and philanderer. The past eight years, since I got sober, have honestly been about trying to peel back each of those habits, to get back to the 12-year-old kid inside who was tremendously excited about life.
PLAYBOY: Give us a snapshot of you in your party years.
SHEPARD: I just loved to get fucked-up—drinking, cocaine, opiates, marijuana, diet pills, pain pills, everything. Mostly my love was Jack Daniel’s and cocaine. I was famous for going out on Thursday night to have a couple of beers, and that just led all the way to Saturday night. I would meet people here and there, and then I’d be in a hotel room with four strangers. Oh, they’re tapping out? Well, someone new showed up. Well, what’s your name? Yeah, I’d love to go dancing. I lived for going down the rabbit hole of meeting weird people. Of course, come Monday I would be tallying up all the different situations, and each one was progressively more dangerous. I got lucky in that I didn’t go to jail.
PLAYBOY: Or worse.
SHEPARD: Oh God, yeah. My nose is completely sideways from a drunken altercation. I’m missing a knuckle because of a drunken altercation. Somehow I was usually able to get sober for work. I got sober for my first movie, Without a Paddle, but then I was fucked-up. I got sober for Idiocracy, but then I was fucked-up for three months. Then, right before I started Zathura, I knew I would get sober for that, so I went to Hawaii to relax, and that’s when things went from bad to worse. I ended up in a car accident with a local on the way to get coke, which didn’t stop us from going to get coke. Then it wasn’t coke, it was crystal meth, but I did it anyway.
PLAYBOY: How exactly did you get a big Hollywood career?
SHEPARD: Well, I spent many, many years unemployed. I was 20 when I moved to Los Angeles. I went on probably 600 commercial auditions and couldn’t book any of them. I went through the Groundlings. Everyone there had agents but me, and it was a ridiculously amazing group. I was there with Melissa McCarthy, who was nominated for an Oscar; Octavia Spencer, who won an Oscar; Tate Taylor, who directed The Help. Success is just a war of attrition. Sure, there’s an element of talent you should probably possess, but if you stick around long enough, eventually something is going to happen, you know?
PLAYBOY: You first got people’s attention as the pretend IRS agent who made Justin Timberlake cry on MTV’s Punk’d. What was that like?
SHEPARD: Because J.T. was such a marquee name, MTV was nervous I would fuck up the bit and we’d have nothing to show for it. His garage was packed full of MTV brass telling me what to do. I wasn’t nervous; it was pure adrenaline. What made Punk’d such a golden opportunity was that once the person arrived, I was directing the show. No one could yell “Cut” or tell me I was going too far. I don’t think I would have popped on a format other than that. You know right out of the gate.
PLAYBOY: You studied anthropology at UCLA. What’s your anthropological assessment of Ashton Kutcher’s success?
SHEPARD: We are incredibly social animals, and we’re constantly searching for some order of who’s alpha, who’s beta, who’s zeta. Ashton’s definitely an alpha. People want to dislike him because he’s gorgeous and successful. It’s fair to hate somebody like that. I relate. If he wasn’t a crazy, driven, hard worker, I would find it all offensive. But he’s like Tyler Perry. How do you not respect Tyler Perry? It’s easy to make jokes about the guy, but he writes, directs and stars on a TV show, then writes, directs and stars in a movie all in one year. And certainly, once you get to actually know somebody, it demystifies them and everything they go through. When Ashton and Demi broke up, I felt bad. These are people I eat dinner with. Brad and Angelina, that’s another story. I don’t actually know them, so I’m as curious as the next person: Will they get married? What’s their life like? And of course I would love to see them engaged in coitus.