When combing through the more than 3,000 articles I’d written for Rolling Stone, The New York Times, and elsewhere to find the most illuminating, vulnerable, adventurous, or weird moments for a new book, Everyone Loves You When You’re Dead, I came to a realization: Almost everything I know about life, I learned from rock stars. Never having gone to therapy, I often used interviews with people wiser, older, or more experienced than myself to work out my own issues and dilemmas. Looking back on the conversations, I can see specific quandaries I was trying to resolve for myself at different stages of growing up. And most have to do with trying to get closer somehow to the purpose of life and the secret to happiness.

Here are five of my favorite moments of illumination from the book.

1. JOHNNY CASH

A lot of times people think that the idea of the man in black is nihilistic, but there’s a positive side to it as well.

Cash: That’s the whole thing. I’ve not been obsessed with death. I’ve been obsessed with living. But, you know, I’ve, uh, in ’88, when I had bypass surgery, I was as close to death as you could get. I mean, the doctors were saying they were losing me. And I was going, and there was that wonderful light that I was going into. It was awesome, indescribable—beauty and peace, love and joy—and then all of a sudden there I was again, all in pain and awake. I was so disappointed.

Disappointed?

Cash: I realized a day or so later what point I had been to, and then I started thanking God for life. You know, I used to think only of life, but when I was that close to losing it, I realized it wasn’t anything to worry about when that does happen.

So did you always believe that when you die you go somewhere else?

Cash: Yeah, but I didn’t know it was going to be that beautiful. I mean, it’s indescribably wonderful, whatever there is at the end of this life.

2. LIONEL RICHIE

Have you thought about putting your experiences into a book?

Richie: I did decide to write about what I experienced in climbing to the top. And finally when I got there, I discovered what was at the top. You know what was there?

No, I don’t.

Richie: Nothing. Not one thing. What was at the top was all the experiences that you had to get there.

3. CHUCK BERRY [While discussing how he gets on a Kubota mower and cuts the grass on his massive Berry Park Estate.]

BERRY: Yessir, because it’s just there and I’m gonna keep the grass cut and all that. I’m a millionaire, but I cut the grass. And each time I cut it, it’s my grass ( laughs and claps his hands). And that is satisfying. Hm-mm-mm.

It’s interesting going with you because every patch of grass has a story and you know the stories.

Berry: Oh yeah, every blade. It’s like a person. A blade is a blade: When it’s cut in half, it dies, for sure. But the half that isn’t cut springs back to life.

Did you just make that up about the grass or is that a quote from something? Because I think it’s true about all the obstacles you’ve overcome.

Berry: No, it came to my mind.

4. HUGH HEFNER

I wonder how much rejection drives people to become stars.

Hefner: Or repression. I think that without question, you know, rejection may be a part of it, but primarily it comes even earlier than that.

So for you, it came from being raised in a home without affection?

Hefner: Yes, although there was a point in time that my mom said she was really sorry and that she herself had been raised in a very oppressive home, so she had been unable to show that affection. And I said to her, “Mom, anything that you may have done that was less than ideal was a blessing. It motivated me to create the world that I have created and accomplish what I have accomplished.” So sometimes it’s the sand in the oyster that creates the pearl. You need some irritation. You need some repression or some conflict. And my life would have been much less satisfying if I didn’t have that.

5. NEIL YOUNG

Perhaps your most often-quoted line is, “It’s better to burn out than to fade away.” But it’s often been misinterpreted, like in Kurt Cobain’s suicide note—

Young: I don’t know. I don’t want to talk about that.

What I was going to ask is what it meant to you.

Young: I think the idea is: Keep on going. Burn! Go! Keep going or you’ll disappear. Now you can take it to an extreme, and some people have taken it to the wild extreme. But the real truth of the matter is that all I’m saying is: If you want to go, go! Go big. Try to do it. To me this is important in whatever I do next. And what I do next is as important as anything I’ve ever done. More important.

Is it difficult, especially when you’re outspoken on different issues, to handle all the requests that come in to do charitable work and benefits?

Young: You got to be selfish. You have to say no. You have to say, “I’m not available,” even though you may not know why you are not available. You have to retain the part of you that is most important for the art, for the work that you’re doing in your life.

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Neil Strauss has written for Rolling Stone, The New York Times, and The Wall Street Journal. He is the author of six bestselling books.