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Arts & Culture

'Tell Me a Story Where the Bad Girl Wins' celebrates pioneering cartoonist Barbara Shermund

Caitlin McGurk won an Eisner Award for Best Comics-Related Book at Comic-Con last year. July 28, 2025
Caitlin McGurk won an Eisner Award for Best Comics-Related Book at Comic-Con last year, July 28, 2025.

When I heard the title "Tell Me a Story Where the Bad Girl Wins: The Life and Art of Barbara Shermund" at last year's Eisner Awards — the Oscars of the comics industry — I had to hit the Comic-Con floor the next morning and buy the book. I mean, how could I resist such a title?

The title is inspired by one of Shermund's cartoons.

"I went back and forth with a million different title possibilities and just kept coming back to that one," explained author Caitlin McGurk. "It's very layered about her story, which you have to read the book to get the whole picture, and what she experienced, how she chose to live, and where her legacy was left when she died, versus the retelling of it to try to bring her back into new light and put her in the actual canon of comics history properly."

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McGurk is the curator of comics and cartoon art at the Billy Ireland Cartoon Library and Museum. That’s where she discovered the art of Barbara Shermund, a name mostly forgotten in history. That discovery inspired McGurk to write her book, which won the Eisner Award for Best Comics-Related Book and recently had its second printing.

Shermund's work graced the pages of The New Yorker and Esquire magazines for decades. She was one of the first women cartoonists to work for The New Yorker when it launched in 1925. She went on to create nine covers and more than 600 cartoons for the magazine. In 1950, Shermund was among the first three women accepted as members of the male-dominated National Cartoonist Society.

Evolution of a The New Yorker magazine cover by Barbara Shermund from the book "Tell Me A Story where the Bad Girl Wins." (2024)
Fantagraphics
Evolution of a New Yorker magazine cover by Barbara Shermund from the book "Tell Me A Story Where the Bad Girl Wins" (2024).

But McGurk did not know any of that when she first came across Shermund's art. It was 14 years ago, and McGurk had just moved to Columbus to work at Ohio State University's Billy Ireland Cartoon Library and Museum. As a transplanted New Yorker, she knew no one in the state.

"So I spent a lot of time, with my lack of social life, just digging through boxes in the collection to familiarize myself with what was held here," McGurk recalled. "And one of those boxes contained really, really stunning original drawings by this artist whose name I didn't recognize — just was signed Shermund — and whose style I was just so compelled by. The jokes were really witty and feminist and edgy. And upon first looking at them, I thought they were probably from the '60s or something. And then soon found out they were by this woman artist who was largely forgotten to time. And they were actually from the late '20s and early 1930s."

Two of Barbara Shermund's The New Yorker cartoons that appear in Caitlin McGurk's book "Tell Me a Story Where the Bad Girl Wins." (2024)
Fantagraphics
Two of Barbara Shermund's New Yorker cartoons appear in Caitlin McGurk's book "Tell Me a Story Where the Bad Girl Wins" (2024).

But McGurk found very little information about the artist: no interviews, few photos, hardly any documents — just the art.

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"I'm someone who just really loves an underdog story," McGurk said. "And the less I can find out about something, the more I really want to know."

That meant telling Shermund's story mostly through her art, which was ahead of its time and still feels insightful, witty and relevant. In Shermund's cartoons, women spoke their minds about sex, marriage and society, often rejecting the conventional thought of the times.

The book not only serves up a lavish and delightful array of Shermund's art but also provides context and analysis. McGurk prompts us to peel back the layers of key cartoons to look more closely at expressions, body language and layout. She reminds us of context — the social mores of the 1920s and '30s that Shermund was challenging.

McGurk noted, "A compelling facet of Shermund’s work, particularly for The New Yorker, is her frequent nods to queer audiences. More than any other New Yorker cartoonist at the time, Shermund’s work seemed to do this the most. There are indications in her personal files that she also may have been queer, including love letters and other personal archives."

I had never heard of Shermund, and I am so grateful to McGurk for highlighting her work and rightfully celebrating her achievements as a trailblazing female magazine cartoonist.

You can hear McGurk discuss her Eisner win in the video below (she is one of the final winners announced):

2025 Eisners: Highlights and backstage

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