Episode 20: Barry Blitt (Illustrator: The New Yorker, Air Mail, more)

Barry Blitt wants you to laugh at him, not with him. Because laughing with him means you’d have to be where he is. And—“thanks very much!”—but he’d rather not. He’s happy enough just drawing for himself.

“I’m trying to make myself laugh,” he says. “That’s the point, that’s part of the process, it’s as un-self-conscious as possible.”

Blitt is a Pulitzer Prize-winning cartoonist and an Art Directors Club Hall of Famer. He’s been called one of the “pre-eminent American satirists.” And, in a recent interview, he was asked what makes him laugh. His answer? “Awkwardness. When people are uncomfortable.”

Which, as it turns out, is right in Blitt’s, dis-comfort zone. In the introduction to his 2017 book, Blitt sums up the effect of all that attention and all those accolades: “I’ve never felt more naked,” he wrote.

Artists are especially prone to self-doubt. They pour their hearts and souls into their creations, whether it’s writing, or photography, or illustration—or cartooning. Then they have to find the courage to put that work out into the world. A world full of critics, and judgment, and rejection.

“I don’t see how the work can be separate from who you are,” Blitt says.

And in today’s explosive media climate, where standing by your work can sometimes mean life or death, Blitt shrugs:

“It’s amazing that I haven’t been punched. But I’m only 65 and, you know, there’s plenty of time for that, I expect. Especially with the hostilities and tensions in the air.”

Regardless, Blitt continues to churn out work. He’s completed over 300 assignments for The New Yorker alone—more than 100 of them covers. That work led to his Pulitzer in 2020, “for work,” the committee said, “that skewers the personalities and policies emanating from the Trump White House with deceptively sweet watercolor style and seemingly gentle caricatures.”

We talked to Barry about how, and why, he made a Time magazine art director cry, about who and what makes him laugh, about his biggest paycheck ever, about what weed can do for your creativity, and about fighting every urge in his body to self-edit.