David Steinberg’s life has straddled comedy’s old and new schools. He was friends with Groucho Marx and palled around with the L.A.-based Hillcrest Country Club gang, including members such as Jack Benny and George Burns. As he chronicles in his new memoir, Inside Comedy, Lenny Bruce was the first stand-up comedian he ever saw, and he grew up to direct Larry David in episodes of Curb Your Enthusiasm.

As a stand-up and on television appearances, the former rabbinical student, now 78, belonged to a generation that pushed stand-up away from mother-in-law and airline-food jokes to something more confessional and confrontational. At Chicago’s legendary Second City, Steinberg’s signature routine was an improvised sermon (“God, whom I’m sure you’ll remember from last week’s sermon…”).

One of those sermons, about Jonah and the whale, was deemed not ready for prime time by CBS censors when Steinberg performed it on the controversial variety series The Smothers Brothers Comedy Hour. That episode, though taped, never aired, and the sermon was instrumental in the series ultimately being canceled in 1969.

Inside Comedy traces Steinberg’s more-than-half-century career while offering insights gleaned from his talk show on Showtime, also titled Inside Comedy, on which he interviewed such icons, torchbearers, and modern masters as Mel Brooks, Billy Crystal, Tina Fey, Gilbert Gottfried, Keegan-Michael Key, Jordan Peele, Robert Klein, Richard Lewis, Don Rickles, and Jonathan Winters.

“I had so many memories over the past 50 years and I wanted to share them,” he told Vanity Fair in an email exchange about the impetus for his book. “I’ve been working on this for a while. I’m so happy it’s finally done.”

This interview was edited for length and clarity.

Vanity Fair: You write that radio was your comedy gateway. Who were your favorite radio comedians?

David Steinberg: We didn’t have a television then. I lived at the movie theater, often skipping school. But radio was the best of everything. You could paint pictures in your head and let your imagination fly. It was so exciting. My favorites were The Great Gildersleeve, The Jack Benny Show, Edgar Bergen and Charlie McCarthy and My Friend Irma. I couldn’t get over them.

You were a rabbinical student when comedy found you. Was there any “Jazz Singer” drama from your parents?

Luckily, I was the baby in the family, not really on their radar. They had already raised three children that were grown (I was a surprise when my mom was 40). They were just relieved that I was going away and doing something that I loved. My dad had a great sense of humor. When I left Winnipeg at 16 to go to Chicago on a scholarship, he said, “I kiss the train that takes you away.”

This is an assumption on my part, but when did you realize that the majority of the people who made you laugh were Jewish, and how did that impact you? 

When I was a kid, I looked around and they were all Jews. In the ’50s, I can’t think of that many comedians who were not Jewish. They were the jazz musicians of comedy for me. They were the outsiders.

Was Lenny Bruce the comedian whom you most related to because he spoke in the language and to the concerns of your generation, much like George Carlin would do in the ’70s? Was he influential in what you chose to talk about onstage?

Lenny Bruce was the first comedian I ever saw. He was a huge influence. He was compelling. He told stories he cared about and never pandered to an audience. He taught me that you could talk about real life, controversial thoughts. I was irreverent because he led the way. It got me in some good trouble over time, like going after Richard Nixon.

You appeared on The Tonight Show with Johnny Carson 140 times. I’m a sucker for Tonight Show debut stories. What do you remember most about your first appearance? 

I was bumped from the show at the last minute three times. The third time my agent Irvin Arthur was irate. “They can’t do this to you! That’s it! We are out of here!” As we were putting on our coats and leaving, Tony Bennett started singing “I Left My Heart in San Francisco.” Irvin turned to me and said, “Wait a minute, we can’t leave. I love this song.” When I finally got on a month later and sat down with Johnny, my life changed. Johnny and I instantly connected. I had a career the next day. I hosted the show when I was 26. I was on the show every few months for over 30 years. Looking back, being on The Tonight Show with Johnny Carson was my career.