Comedy Legend David Steinberg on What it Takes to Be Funny

Old picture of David Steinberg on the Tonight Show in 1970

The comedian and host of Inside Comedy discusses his new book on a life of laughs.

In the ‘60s and ‘70s, Canadian comedian David Steinberg was one of the best-known comics in the United States. He’s worked with every comedy legend from Larry David to Carol Burnett, and has seen firsthand the meteoric rise and tragic downfall of comedic trailblazers like Lenny Bruce and Richard Pryor. Steinberg is a comedic heavyweight, and has more than 130 appearances on the Tonight Show to prove it.

His new book Inside Comedy, is named after his talk show, where he speaks one-on-one with some of the funniest people in show business. The book chronicles Steinberg’s decades-long career in the industry, and the incredible people he’s met along the way. It’s delightful, insightful, and will give you a new appreciation of what it takes to make an audience laugh. We spoke with Steinberg about his favorite comedians, his proudest moments, and what it takes to be remembered in such a cutthroat industry.

“At the Vanity Fair Oscar Party with two of my favorite people, Martin Short and Larry David, February 2016. I think that’s the night that Larry disappeared for an hour and took a nap on one of the couches outside during the party, but I could be mistaken.” – Steinberg

KCM: You say that every comedian borrows from those who came before them. Have you ever seen someone perform who you thought was truly original?

David Steinberg: The Beatles were inspired by great blues and R&B artists, but they were still The Beatles and still a one-of-a-kind iconic group. Comedians are no different.

Every comedian is inspired by someone, whether it’s another comedian, a friend, or a family member. They take that style and make it their own. Although there are many comedians that are extremely talented and unique in their own way, from Jerry Seinfeld, to George Carlin, to Lily Tomlin, to Richard Pryor, I think Lenny Bruce really paved the way. He had a raw honesty in his storytelling. The way he walked the stage and the way he dressed, a nehru jacket and cool suits: He was unafraid. Lenny inspired a new level of raw honesty in comedy. It touched everyone. 

“John Candy and his family lived in my guesthouse in Los Angeles for a year while we were writing and shooting the cult classic Going Berserk, circa 1982. John wrote most of the script on a napkin. That should tell you something.”

You compare comedy to music quite frequently in the book. Do you think an appreciation of music is crucial to being a good comedian? 

I opened for a lot of jazz musicians like Miles Davis and The Modern Jazz Quartet. Jazz and comedy are similar in that they both have a rhythm, and that both need deep listening to enjoy them. And it’s not a coincidence that musicians are some of the funniest people on the planet. Timing is everything for comedy and music. Comedians work hard on their rhythm. It’s as much work as the material itself. Take away the rhythm of a great comedian’s work and you have no instruments, just lyrics. In other words, no laughter. 

Think about Jack Benny’s use of silence. The perfectly placed and timed beats of silence. His silent beats were as important as his written jokes. 

“Two of my best years on the road were spent with Robin Williams (here on our plane on tour in 2014). We traveled the country and had dinner together after every show. He never stopped asking me questions. We never stopped laughing. But I remember every morning he would go out by himself and explore the new town we were in. He would walk into local shops and shock people in the stores. He was so casual about it. He was loving, unique, funny (the funniest). There will never be anyone like him.”

You mention Key and Peele as some of your favorite guests on Inside Comedy. Why? 

Keegan and Jordan are smart, unique, and brilliant improvisors. They played off each other…and me. There was a spontaneity they had with each other. It was a different kind of interview. It brought me back to my time with Second City.

I directed Keegan in a pilot called Frangela, written by and starring Frances Callier and Angela V. Shelton, several years back and it was obvious how talented he was then. Most everyone I interviewed — from Robin Williams to Larry David to Chris Rock to Sarah Silverman, Jerry Seinfeld, Mel Brooks and beyond was equally exciting for me in different ways. I love comedians and comedy. Always have. Inside Comedy allowed me to get inside the minds of the best of the best, and it doesn’t get better than that.

“Hosting Movies, Movies, Movies with my guest Richie (Richard Pryor), January 17, 1974. We took any opportunity to be together. Just a few years later, Richie’s daughter Rain came to stay with my family for a while. She was adorable and smart, and Richie adored her. Also in photo are Paula Kelly and Roscoe Lee Brown.”

You say that Richard Pryor’s comedy at the beginning of his career was groundbreaking and brilliant and outrageous, but that ultimately drug use led to his downfall. Do you think comedians like Pryor and Lenny Bruce would have continued to rise in popularity if it hadn’t been for their drug use, or do you think it’s part of what made them who they were? 

That’s a difficult question. There were a lot of drugs in those days. Second City had its fair share, and the stand-up comedians did as well. Honestly I believe it probably both helped them and hurt them. I will say, it hurt their audiences tremendously. I wish they all could have made us look at the world and laugh for many more years. I believe they would have continued to rise in popularity without the drugs. That’s a huge loss.

“Before going on The Tonight Show Starring Jimmy Fallon, 2015. It was great being back at the same old Johnny Carson Tonight Show set in New York City after so many years. It’s still the same setup. I instinctively knew where to enter the stage. It was all so nostalgically familiar to me. I missed Johnny, but Jimmy Fallon belongs there now.”

Some of the comedians you talk about as the “all-time greats,” or “geniuses,” like Jonathan Winters and Sid Caesar, are names that haven’t really stood the test of time. What do you think it is that gives a comedian lasting power even after he or she dies or stops performing? 

First, the medium you’re in determines who can be remembered. Movies last forever and are easy to watch — so Peter Sellers, Charlie Chaplin, and Abbott and Costello are still remembered. Sid Caesar was just as brilliantly funny, but you can probably only find him on YouTube. Why do young folks know Jackie Gleason and not Sid Caesar or Jonathan Winters? The Honeymooners. It ran through generations and hasn’t slowed down. Your parents knew every line, and now you do too. 

Here’s a fact: Someone once asked professional baseball players to say something about Lou Gehrig. Some could say he was a NY Yankee, but couldn’t name any accolades. Not that he held the longest hitting streak in baseball history. Yet, he was the best of the best, and certainly the best of his generation. People move on to the next flavor. People used to like corn. Now it’s kale. I don’t know what that means but it sounds intelligent…and healthy.

“One of my favorite birthdays with Don Rickles, Marty Short, Bob Newhart, and of course my wife, Robyn, who threw the party at E. Baldi restaurant in Beverly Hills, August 9, 2014.”

Is there a specific joke or bit that you remember from another comedian that you think is the funniest you’ve ever heard?  

The 2000 Year Old Man“— Mel Brooks and Carl Reiner. Nothing else ever came close. And it stands the test of time.

In your long and illustrious career, what are you most proud of?

I’m most proud of being a Canadian and receiving The Order of Canada. My family and my teacher Miss McCrumb who desperately tried to make me amount to something are probably looking down, shocked and kvelling with pride and disbelief.

“With Wanda Sykes, a brilliant comedian and comedic actress, on the set of Inside Comedy. A true joy to be around.”

Of everyone you’ve mentioned in the book, is there anyone you haven’t interviewed, or seen perform, that you’d like to?

 Moses.