A legend looks back In his new book, Winnipeg-born comedian David Steinberg reflects on 50 years of laughs By: Ben Sigurdson Posted: 7:00 PM CDT Tuesday, Jul. 20, 2021 Last Modified: 7:26 PM CDT Tuesday, Jul. 20, 2021 Updates

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When you’ve had a career in show business as illustrious as David Steinberg’s, it could be hard to be humble.

But the 78-year-old comedian, director and writer is exactly that — modestly proud of his achievements and downright deferential to his peers, mentors and the next wave of entertainers, as is evidenced throughout his new book, Inside Comedy: The Soul, Wit, and Bite of Comedy and Comedians of the Last Five Decades.

Maybe it’s just the Winnipeg in Steinberg coming through.

Born in 1942 to Yasha and Ruth Steinberg, David, his parents and three older siblings lived in the North End, surrounded by many other Jewish families. David’s early schooling involved attending a private Hebrew school before switching to West Kildonan Collegiate Institute.

His comedic chops were already being formed. “(I)t was my first time in a public school, my first time seeing these gorgeous girls and boys who were all taller than I was,” he writes in Inside Comedy. “Despite these handicaps, I could still control the class. I wouldn’t say I was a ‘s— disturber,’ but I had a way of talking to the whole group, and I was funny.”

Interviewed by email prior to Thursday’s launch of Inside Comedy, co-presented by McNally Robinson Booksellers and the Winnipeg Comedy Festival, Steinberg, now based in California, recalls the ways in which his comedic wiring began to take shape in the city.

“Winnipeg was the perfect-sized town — everyone knew each other. My friends were funny — we made each other laugh. No one had a television. Our entertainment came from each other. It was a great place for creativity.”

His decades-long comedic career is chronicled in Inside Comedy, weaving its way through interviews with and musings about comedic legends past and present. The book, written and compiled by Steinberg during the pandemic, riffs on the show of the same name, hosted by Steinberg between 2012 and 2015 (and available to watch on Amazon Prime Video). Most of the other voices in his book — comics of all stripes, a veritable who’s who of talent — were guests on Steinberg’s show, their answers first conveyed to him there.

Among those other voices are comedic legends (and old friends) such as Carl Reiner, Bob Newhart and Bette Midler, as well as the next generation of talent including Sarah Silverman, Zach Galifinakis and Julia-Louis Dreyfus. “They can still make me laugh,” muses Steinberg on the process of pulling the book together.

Steinberg’s entry into comedy could be described as divine intervention. His father was a rabbi, and by all accounts young David looked set to follow in his footsteps. He undertook rabbinical studies in Israel before leaving Winnipeg for Chicago at age 16 on a scholarship, where he eventually studied English literature.

But seeing comedian Lenny Bruce’s edgy, fast-paced standup act flipped a switch for Steinberg, and he realized he was destined to be in comedy. He joined Chicago’s Second City shortly thereafter, honing his chops with the likes of Fred Willard, Robert Klein and Joe Flaherty.

Steinberg’s early act typically featured comedic “sermons,” conversations with God or musings on the Old Testament and religion, some of which were gleaned from his own childhood experiences and religious education. It was edgy and provocative without delving into the profane, garnering Steinberg plenty of attention, as did his tackling the political hot-button issues of the day, particularly during the Nixon era. He’d eventually move from Chicago to New York, landing work on Broadway and the odd TV hosting gig. Combined with his comedy albums, Steinberg was making quite the name for himself.

Then there was The Tonight Show Starring Johnny Carson. Starting in 1968, Steinberg appeared on Carson’s late-night talk show 140 times (second only to Bob Hope), including a number of fill-in hosting gigs, the first of which he got at the tender age of 26.

Years later, when honing his own interview skills for Inside Comedy, Steinberg needed look no further than his longtime friend and Tonight Show host. “I started with Johnny Carson, and that was all the inspiration I needed,” he recalls. “You just need curiosity. I’m especially curious about how people think, especially people in comedy.”

Steinberg’s credits — on stage or screen, behind the camera and elsewhere — are too numerous to mention in one article. He cut his teeth on The Smothers Brothers Comedy Hour, his fictional sermons racking up numerous complaints and possibly helping lead to the show’s cancellation. He had a number of hosting gigs, including The David Steinberg Show, a Canadian program which aired in 1976-77 (and is also available to watch on Amazon Prime), featuring a cavalcade of comedic names as guests, in addition to pre-SCTV appearances by the likes of John Candy, Martin Short, Andrea Martin and more. His four comedy records, released in the late 1960s and early 1970s, earned him a pair of Grammy nominations and inspired countless comics then and now.

In more recent years Steinberg turned to directing, his work behind the camera on shows such as Friends, Mad About You, Seinfeld, Weeds and Curb Your Enthusiasm, earning him two Emmys. He spent two years on the road performing with the late comedian Robin Williams, dining (and laughing) with him almost every night before Williams’ death in 2014. And at a 2017 ceremony, Steinberg was made a member of the Order of Canada. Inside Comedy takes readers through all of it.

Today’s trend of YouTube videos, TikTok comedians and standup specials delivered on streaming services has drastically changed the comedic landscape. Asked whether he figures it’s easier or harder as a comedian today, Steinberg is of two minds.

“Both, really,” he says. “It’s much easier because when you’re on social media, you essentially have your own channel. You are in effect a broadcaster, and you can connect with people that think the way that you think. So once you get a fan base who thinks like you do, you have created an audience by algorithm who will laugh at the same things you do.

“The flip side, however, is that you can alienate people very easily on social media.”

The world of late-night talk shows has similarly changed since Steinberg’s heyday on The Tonight Show. On-demand viewing means viewers need no longer tune in at a particular time, instead opting to watch their favourites whenever they want. Most recently, late-night stalwart Conan O’Brien, one of the many voices featured in Inside Comedy, has hung up his talk-show microphone to pursue other interests. But Steinberg sees a future for the genre. “Things always change over time,” says Steinberg. “Hosts will change… I believe there will always be some form of late night.”

With his feet planted firmly in both the standup and directing worlds, Steinberg still keeps close tabs on the best and brightest of the next generation. “There are so many great talents coming up today. There are so many. For directing, Jordan Peele (Get Out, Us) is one of my favourites, and Sebastian Maniscalco comes to mind as a comedian,” he says.

Asked for final words for his hometown audience, Steinberg shows genuine appreciation for his roots. “I loved growing up in Winnipeg and everything that entailed — skating to school, playing basketball, attending Talmud Torah, attending West Kildonan… I loved being a counsellor at the B’nai Brith Camp. Basically, I just loved growing up in Winnipeg.”

The virtual launch of Inside Comedy is in the form of an exclusive film about the book, created by Steinberg and his wife, Robyn Todd. It features the comedian talking about his life and the book, as well as some behind-the-scenes footage and interviews with collaborators such as Chris Rock, Larry David, Martin Short, and others. The film will only be available for viewing at 7 p.m. on Thursday; registration is required

ben.sigurdson@freepress.mb.ca