David Sipress was born and raised in New York City. He graduated from Williams College in 1968 and went on to study Russian History in the Department of Soviet Studies at Harvard University. He left Harvard before completing his degree to pursue a career as a cartoonist. 

David has been a staff cartoonist at The New Yorker since 1998. He’s published nearly seven hundred cartoons in the magazine. During the presidential election in 2012, he became the first Daily Cartoonist on The New Yorker website, and repeated as Daily Cartoonist in 2014 and twice in 2016, covering the presidential primaries and the national election. His topical Daily Cartoons continue to appear on newyorker.com in 2021. His cartoons have also appeared in Time, Parade, Playboy, Funny Times, The Washington Post, Harper’s, Men’s Health, Gastronomica, Shambhala Sun, Narrative, Süddeutsche Zeitung, The Spectator, Air Mail Weekly, and numerous other publications and related websites. He was the weekly cartoonist of The Boston Phoenix newspaper for twenty-five years.

He was the 2016 winner of the National Cartoonists Society’s Reuben Award for Gag Cartooning.

David has published eight collections of his cartoons, and his drawings appear in many New Yorker cartoon collections, including “The New Yorker Encyclopedia of Cartoons” and “The Complete Cartoons of The New Yorker.”  They also appear in “The Rejection Collection: Cartoons You Never Saw, and Never Will See in The New Yorker,” in “The Best of the Rejection Collection” and “The Rejection Collection, Volume 2”.

David was the co-creator, writer, and host of “Conversations with Cartoonists,” a series of onstage interviews with New Yorker artists, including Roz Chast, Gahan Wilson, George Booth and many others, at Dixon Place Theater in New York City. He has been interviewed about his work on NPR and on Sixty Minutes. He has lectured widely on his work and the art of cartooning, including at the Rubin Museum in New York City, the Center for Cartoon Studies in Hartford, Vermont, the Yale Art Museum at Yale University, and Williams College. He’s even lectured on the Queen Mary II, during a stint as the Cartoonist at Sea– a collaboration between Cunard Lines and The New Yorker.  Videos of these talks have garnered many thousands of views.

In 2015, The New Yorker produced a short film about David: “The Making of a New Yorker Cartoon.” It has over 20,000 views on YouTube.

David has published seventeen personal history essays on the website of The New Yorker, newyorker.com In February, 2017, he appeared on MSNBC (“AM Joy–The Joy Reid Show”) and on The Canadian Broadcast Corporation to discuss his New Yorker essay, “How to Stay Sane as a Cartoonist in Trumpland.”

He lives in Brooklyn with his wife, Ginny Shubert, an attorney and activist who works on issues of health and housing.