Few comedians have second and third careers. If they have their acts down pat and audiences love them, why change? Buster Keaton stuck to what he knew, as did Jack Benny, Joan Rivers, Jerry Seinfeld … well, you can make your own list.

David Steinberg is an exception, since not only did he enjoy a brilliant career as a comedian, but he also branched out into successful careers as director, interviewer, and writer. His latest book, Inside Comedy, is an astute and entertaining reflection on who and what has made people laugh over the past 50 years. And to think he could have also been a rabbi!

Jim Kelly: You make it clear in your book that a truly happy person makes a terrible comic. As you put it, “If you’ve had a great life and a wonderful Bar Mitzvah and you’ve been given a lot of money, you’d make a lousy comedian. You’re better off being the comedian’s lawyer.” A writer needs a wound, as you put it, and you experienced a very painful wound when you were quite young. Can you tell us what happened and how it shaped you?

David Steinberg: When I was four years old, my family was happily celebrating Passover in our home in Winnipeg. At some point the doorbell rang and I ran to get it. The man at the door gave me an envelope, and I happily ran to give it to my parents. Turns out it was informing us that my 19-year-old brother, Haime, had just died. He was a pilot gunner during World War II, and his plane crashed. My whole family went from joyous to screaming and crying, and I don’t think my mother left her room for four years.

I suffered from depression over the years but never made the connection. I never talked about my brother as I never knew him. But, in my 40s, I told a therapist the story, and he said, “Don’t you think it makes sense that a young child who makes an entire room cry might want to spend his life creating laughter?”

From left, Steinberg, Richard Pryor, Paula Kelly, and Roscoe Lee Browne. “He changed the game,” Steinberg says of Pryor.

J.K.: Not many comedians both come from Canada and studied to be a rabbi. How did those two experiences shape you?

D.S.: Every life experience, every relationship in life, shapes who you are. Canada was a quiet haven for up-and-coming comedians. And my life experiences and view of the world from Winnipeg certainly gave me a unique point of view.

As for studying to be a rabbi, well, ask Tom or Dick Smothers. My sermons contributed to getting them thrown off the air, and they were the No. 1 show at the time. My depth of knowledge of religion gave me a whole new fertile and unique well of material that no one was tapping into. No one has used Moses in more material than me. Today he’d be getting residuals.

J.K.: The first stand-up comedian you saw perform was Lenny Bruce, and you later became friends with Richard Pryor, who you called “Richie.” Both were brilliant, and both self-destructed. Does such comic genius inevitably carry the seeds of ruin?

D.S.: I luckily escaped that. It was all around me.

Lenny Bruce was intense and passionately defiant. He was an amazing candle that you could sense was going to burn out too soon. A shame.

Richie was a brilliant star. He changed the game, he owned it, and he was adored. He came from a troubled background and childhood. That’s a heavy mantle to manage every day of your life.

I don’t believe comic geniuses necessarily carry the seeds of ruin. I think people who struggle and reach success by failing first before they are accepted and loved come with a lot of insecurity. That “When are they going to find me out?” syndrome is a heavy burden for geniuses of all kinds. People don’t think of themselves as geniuses—other people do. That’s a burden.

Steinberg during an interview with Johnny Carson. “We are all performers. We all had a public side and private side,” Steinberg says.

J.K.: You were good friends with Johnny Carson and appeared on or hosted The Tonight Show more than 130 times, a record surpassed only by Bob Hope. How much were you aware of Carson’s own dark nature and the kind of despair that Peter Lassally, his producer and a mutual friend, has described?

D.S.: I didn’t see that side of Johnny. I didn’t want to. We spent a lot of time together having lunches and dinners and parties and always had a lot of laughter. I was never a late-night person and not a big drinker (though I did like a cigar), so maybe that’s why. Again, we are all performers. We all had a public side and private side. Sometimes the private sides are deeper and darker than we know. We’re all human. Even Johnny.

J.K.: You have directed too many sitcoms to mention them all, many with actors with egos that, well, let’s call them “healthy.” I am too polite to ask you which was your worst experience, so I will ask you which has been your best experience so far.

D.S.: Curb Your Enthusiasm has been a delight. Brilliant talent, a loose set. And people I love being with. Also, directing Bob Newhart on his show was a wonderful experience. I loved everyone on the show, and every day Bob would ask who I wanted to have lunch with. Don Rickles, Dick Martin, Dick Shawn, Lucille Ball … every day was a party at the commissary.

J.K.: I am also too polite to ask you who you think is the most overrated comedian you have known. But I will ask you who you think is the most under-appreciated. And the best overall?

D.S.: Under-appreciated: I’d say Bernie Mac. For me he doesn’t seem to get mentioned in the upper hierarchy of the greatest of the greats, but I thought he was, and I would bet many great comedians would agree.

Best overall: impossible. How do you choose “the best”? Who was better than Robin Williams, Richie Pryor, Lenny Bruce, Phyllis Diller, Rickles, Chris Rock, Eddie Murphy, Billy Crystal, Jonathan Winters, Joan Rivers, Wanda Sykes … I could go on. Who was better than them? No one. They were all the best at what they did. All different. All great. The best? I’ll let you pick one.

Steinberg and Burt Reynolds in New York City, 1980.

J.K.: You describe so well how comedy has changed over the years. Is it harder today for a comedian to have a breakthrough moment than it was 40 years ago?

D.S.: Yes and no. On the one hand you have YouTube, so there’s an automatic audience. We had to get up onstage every night to hone an act. We loved it. But today that’s more difficult because of cell phones and fear of being “canceled.”

Stand-up is all about taking risks and failing. You need the freedom to talk about anything. It’s much more complicated today. Controversy and pushing the envelope was all we did. Nothing was off-limits. There were repercussions, of course. Going up against Nixon had me followed by the F.B.I. And my religious sermons contributed to the cancellation of The Smothers Brothers Comedy Hour.

J.K.: All of this brings me to this question: You are not only highly successful but you seem like a very happy person! You have a wonderful marriage, and in your much-praised career as director and interviewer you seem genuinely interested in bringing out the best in others. How have you managed to pull this off?

D.S.: Luck.

David Steinberg’s Inside Comedy: The Soul, Wit, and Bite of Comedy and Comedians of the Last Five Decades is out now from Knopf

Jim Kelly is the Books Editor for AIR MAIL