Author and film critic Shawn Levy remembers driving across the state line In 1992 and seeing the “Welcome to Oregon” sign. “I had the conscious thought, ‘I’d like to write books and be the film critic of The Oregonian.’ And both of those things happened. But if I knew ‘they’ were taking requests, I would have said something about money.” 

Levy earlier this summer released In on the Joke (Penguin Random House, 2022), a nonfiction project in which Levy explores the controversial and largely unknown history of women in comedy, chronicling some of the first female stand-up comedians, improv performers, and groundbreakers in the business. The book was recently named “one of the best comedy books of 2022 (so far)” by entertainment website Vulture.

In on the Joke started out as something else, Levy said, explaining he had an idea for a book about politics and comedy, and how the culture had changed. “In the ‘50s, nobody told jokes about politics. You would joke about how President Eisenhower was a poor golfer. That was as current as most comedians were,” he said. “Now, you go to comedy shows and an entire set can be about politics. We have comedy shows about politics on daily TV. So, how did that happen? What was that change like?” 

One of the chapters he proposed was about women entering the comedy mainstream in the late ‘50s and early ‘60s. “The publishers rejected the comedy and politics idea, but they liked that chapter. Suddenly, at that point, I thought I knew exactly what the book would look like.”

Originally from New York City, Levy got his start writing for Boxoffice Magazine, the oldest film-only trade magazine still in business, and American Film, for which he visited the set of The Godfather Part III and met film celebrities including Spike Lee and Steven Spielberg.

Levy said he grew up surrounded by journalism. “My dad had wanted to be a writer as a young man and wound up having to support a family, so he encouraged me. I was involved in newspapers in middle school, high school, and college, and then I got interested in poetry and wound up getting an MFA in poetry — but then I became a dad and had to support a family and luckily I found a journalism job that could begin to do that, and I’ve been full-time writing for a profession since leaving graduate school in 1988.”

In 1992, American Film folded, and Levy moved to Portland six months later, where he began to write books, balancing that with his journalism career.

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“There was a time when I was writing books and I was working full time at The Oregonian, and I would take leaves of three months at a time to stop writing daily journalism and switch to the longer stages of the book-writing marathon. I would take research trips worldwide and file stories for the newspaper from those places,” he said.

Besides writing for the New York Times, the Los Angeles Times, The Guardian, The Independent, and the San Francisco Chronicle, Levy has authored several books, including The Castle on Sunset, The Rat Pack, and Paul Newman: A Life. Comedian Rita Rudner praised In on the Joke as “insightful and impeccably researched,” and Margaret Cho called it “a seminal work on the incredible journey of women in comedy.”

We talked with Levy about In on the Joke and his writing process. His comments have been lightly edited for length and clarity.

You’ve written about some of the world’s best-known actors, artists, people, and places — Paul Newman, the Rat Pack, Robert DeNiro, Jerry Lewis, the Château Marmont — how did you start down this path and how do you choose your subjects?

Levy: My first book idea was about Pedro Almodóvar, this was right after Women on the Verge of a Nervous Breakdown and Tie Me Up! Tie Me Down!… He was this cool, sexy new presence in European cinema. And I asked writer friends for their agents, and a woman took me on and didn’t get anyone interested in the Almodóvar book, but they thought, “What other ideas does he have?” I began to think about what people I would want to read a book about, or people whose whole career I would want to learn about or watch. I saw there hadn’t been a book about Jerry Lewis in at least 20 years. While I wasn’t a huge Jerry Lewis fan, I knew he had been busy and I knew there were enough interesting things about him.

While I was writing about Jerry Lewis, I changed agents, and we’ve been working together for around 30 years now. When I finish a project and am editing, we’re looking ahead to the next one. I keep a folder of ideas and occasionally he says, “Yeah, write that up,” then he proposes changes and we submit it to the current publisher. It’s a collaboration with my agent — choosing subjects — looking at the bookshelf, as it were, and saying, “Well, there’s a hole here.”

There was a previous book on the Château Marmont written in the ‘70s. My book came out in 2019. So the whole modern history of that hotel is very different from what these people wrote previously. Château Marmont in the swinging ‘60s… I’d randomly say to people, “Tell me a Château Marmont Story,” and they’d say, “Oh man, I’ve got three!”

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What is the most surprising thing you’ve learned while researching this book?

I didn’t think I would write about Moms Mabley. I didn’t think I would write about Minnie Pearl. To me, these were women working in a very narrow niche of showbiz. As I kind of vetted them with the thought that I was going to “pass,” I realized that they were doing exactly what Joan Rivers and Phyllis Diller did decades later — and they were doing it in complete isolation. They would not have heard of each other. Jean Carroll, another woman working from the ‘20s to the ‘60s, wouldn’t have heard of them either, because they were all working in such narrow rivulets of show business. Then I realized that this story goes back decades before I thought it did, and I can honestly say that there is something on every page of this book that was news to me, which is terrifically exciting.

How has comedy changed since the pandemic, especially for women?

Contemporary comedy is not really my area of expertise, but what I do know is that there are more opportunities today for women comedians than there have ever been. I honestly feel like 10 years from now, there will be even more opportunities. There are so many more ways for women comedians’ voices to be heard. That being said, they are still fighting the same fight. Looking at the current landscape, the only woman to ever appear on the Forbes top-10-earning comedians in showbiz list was Amy Schumer — never higher than fifth or sixth, behind a ventriloquist who performs in Las Vegas. And I think, “Really?” Women who we identify with as comedy superstars — Sarah Silverman, Wanda Sykes, Tina Fey, Margaret Cho, many others — somehow never get in the top 10. The opportunities are there, but the reluctance of the gatekeepers is still quite vigorous and the overall prize is still smaller.

Do you think contemporary female comedians face similar or vastly different career hurdles than the pioneering women of comedy?

Comedians now can go straight to an audience. You can do it from your home with a microphone and an internet link, which is amazing. It’s harder to stand out in that, however. But it used to be that the gatekeepers did or didn’t let you in, and then you are a household name. The chance of being a household name any longer seems to be decreasing, even though it’s easier to get to a certain stable level of the profession.

Who is your favorite comedian and why?

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In the book, the genius for me is Elaine May. She was never a stand-up per se, but she is indisputably one of the inventors of improv comedy, which is one of the dominant forms in the last 60 years. Everyone who was on the ground floor with her when improv was starting in Chicago at Compass Theatre, which became Second City, said that she was the best writer, performer, sharpest wit, scariest… people were scared to be on stage with her because she could improv circles around them.

What role does comedy have in your life, and what role does it have in our society today?

I’m happy that I don’t make my living doing comedy. Will Smith does this crazy thing on one of the biggest stages you could possibly be on, and weeks later someone runs on stage and attacks Dave Chappelle. This isn’t how we’ve agreed to behave in the past, so there is still a period of uncertainty around us. It makes sense that a comedian can be afraid. It went from “they’re going to cancel me” to “they’re going to punch me in the face.” That’s got to be chilling. It’s got to be chilling to free speech and free thought. Belle Barth, one of the women in the book, was arrested more than six times in the ‘50s and sued for emotional damage by someone in the audience who heard her tell naughty jokes. So that existed, and then it didn’t, and now we’re back to it again.

Comedy is such a quick-responding art. A world event happens and we wonder, “How will they deal with this in comedy clubs?” If somebody wanted to respond to an event in a film or music, it might take years. But comedians are expected to be the tip of the spear and be fearless. I remember the post-9/11 vibe around David Letterman coming back on the air… we expected comedians to respond, which was a bit strange. As I said, there was a time when we would never dream of a comedian talking about contemporary events; it was all about mothers-in-law and airline food. It functions as a collective thing. If Twitter didn’t exist, comedy is the next closest thing to that 280-character public forum.