Oprah: And you did that because you felt like, This is my chance?
Billy: Yes. Freedom. That was the greatest single gift I've ever received.
Oprah: Were you afraid?
Billy: Terrified. Every day we'd been watching this war on television, and it made no sense at all to me.
Oprah: And every day, we'd hear the death toll.
Billy: It was like a telethon: "We're up to 23,000 men killed." It was just an ugly time.
Oprah: So you moved forward—with fear.
Billy: I was hiding with this comedy group for four years. I loved my friends, and we were pretty funny, but I should've been out there by myself. A friend from NYU called me and said, "I need a comic for a frat party on Saturday night. Do you know anyone who can do 15, 20 minutes?" I said, "I'll do it." He said, "When did you start working alone?" I said, "I've been doing it for a while." Lie. He said, "Great. It's at 8 o'clock at the ZBT House on Mercer Street." I was like, "What the hell did I just do?" I hung up, then turned to my 18-month-old daughter and said, "Baby, we're going into show business." I had, like, six minutes of material. So I drive in, and I'm terrified. There are all the kids, sitting on the floor, waiting for the show to start. Then I hear, "The folksinger is delayed. Can you stretch?" I say, "Oh, sure." Now I'm more panicked than ever. Forget the draft—this was really scary. That night I did an hour and a half. I still don't remember what I said.
Oprah: An hour and a half?
Billy: I went berserk. What came out was all the years of frustration with the group. Jack Rollins—the guy who managed Woody Allen, Robert Klein, Dick Cavett—was in the audience, because he'd just started managing our group. A few months before, he'd said to me, "The group's not going anywhere, but if you think you want to do stand-up, I'll be there for you." Since I'd booked this gig myself, I said, "Listen, I'm getting $25, and I'm not paying you a commission." He showed up anyway, in pouring rain. Afterward he said, "Everything you did pretty much stinks, but let's go to work." The next night, when I told the other guys I'd done this, I felt like I'd cheated on them. They were dear friends. I said, "I can't do this anymore. I have to go out and try on my own."
Oprah: Did they understand?
Oprah: Did you take the baby with you to your shows?
Billy: I did. Back then my wife was working at a college, as an assistant to the dean of theater.
Oprah: I read somewhere that one of your saddest days was when Jen said, "I can wash my own hair now, Dad."