PLAYBOY: Have you had any cravings during the pregnancy?
WENTZ: She craves pickles and pizza and Popsicles. And green olives go on almost everything.
SIMPSON: Yeah, I’m into olives. Well, you guys get back to it. I’ll go back to my dogs. [She leaves.]
PLAYBOY: What’s the toughest part of Ashlee’s pregnancy for you?
WENTZ: She goes to bed at eight, and I have one of the worst cases of insomnia on the planet, so it’s just me and the dogs, hanging out. You don’t even know the transcendent conversations we have.
PLAYBOY: How bad is your insomnia?
WENTZ: If I don’t take an Ambien, I’ll sleep for an hour. With Ambien, I’ll sleep from two a.m. until seven. But if you don’t fall asleep, Ambien makes you hallucinate. About four months ago I took Ambien and almost set the house on fire.
PLAYBOY: Is insomnia the key to being in a band, running a record label, having a clothing line and maintaining four blogs?
WENTZ: Fortunately, I have a bit of a Reagan administration, where you just surround yourself with brilliant people and then they credit you with all the ideas, when there’s really someone else a lot smarter doing the job better than you could.
PLAYBOY: You’re likening yourself to Ronald Reagan?
WENTZ: [Laughs] That’s great. I’m sure that will get me in plenty of trouble.
PLAYBOY: So you like prescription pills. How much experience have you had with illegal drugs?
WENTZ: I don’t know if I want my mom to read this. Let’s just say I haven’t tried anything you have to stick into your veins. I’ll tell you my ecstasy experience: I was 13 or 14 and did ecstasy and acid at the same time. It’s called candy flipping. Terrible. I was puking, and then the puke would wash off me because I was hallucinating, and the clock was moving backward. Everyone else was like, “Let’s smoke menthol cigarettes and give massages.” I learned quickly that I don’t like drugs that make me hallucinate.
PLAYBOY: When you were 14 you were sent to a boot camp. Were you a bad kid?
WENTZ: No, I was just directionless. I didn’t want to go to school—I’d skip and go skateboarding. So I had to see a counselor, and she strongly suggested I go to this boot camp in New Hampshire. The place later burned down, and the counselor who sent me there broke her neck and passed away, which is crazy.
PLAYBOY: Do you think you needed to go?
WENTZ: No. If anything, it caused essential changes in my personality that were not good. I was on the phone with my parents every day, asking them to take me home, because the place was filled with all kinds of maniacs. They didn’t believe me.
PLAYBOY: So how did that change you?
WENTZ: I’ve never met anyone who is less in touch with his emotions than I am. People make all kinds of confessions to me, and I have zero emotional reaction. The only two times I can remember crying are during Click, the Adam Sandler movie. I can communicate only by writing to someone or writing a song. In a one-on-one relationship I’m an android, like Data from Star Trek.
PLAYBOY: Has therapy helped?
WENTZ: I have a tendency to lie to therapists. In our song “Thriller” the line “Fix me in 45” isn’t a reference to a 45 rpm record; it’s a reference to a psychiatrist’s hour, which is 45 minutes. I don’t think I can be fixed. I see it like the Liberty Bell. Are you supposed to fix that crack? Then it’s not as interesting. I’m drawn to imperfections. All my heroes are tragic.
PLAYBOY: So what’s imperfect about Ashlee?
WENTZ: In Ashlee’s world, the world of Hollywood, she is the black sheep.
PLAYBOY: How did Fall Out Boy fans feel about your dating a singer who had been caught lip-synching on Saturday Night Live?
WENTZ: At first they were not superstoked. They said, “She’s fake. She’s Hollywood. She’s ugly. She’s a typical fake whore.” For a second she was getting the Yoko Ono rap, which couldn’t be further from the truth.
PLAYBOY: Did you see the SNL episode with her as the musical guest?
WENTZ: I saw it after it was broadcast. I think it’s funny how some people are singled out when it’s obvious a lot of people use backing tracks. The only thing I took away from it is that she’s the kind of person who always gets up after being knocked down. People won’t ever see Ashlee the way I do. I feel like a guy who found the end of the rainbow and has the leprechaun tied up in the corner.
PLAYBOY: Does Ashlee make good music?
WENTZ: Ashlee makes awesome music. I love “Little Miss Obsessive,” and I love “Boys,” which is a total gay anthem, by the way. I liked her music before I even met her.
PLAYBOY: How are Ashlee and Jessica alike?
WENTZ: Ashlee and Jessica are both like Dennis Rodman—they’re rebounders. They get back up again. Jessica is America’s sweetheart; she’s the girl next door but hotter. She has a big, forgiving heart. Ashlee marches to the beat of her own drummer.