A fighter pilot, Cullum came home from Vietnam and went to work at TWA as an airline pilot. But he was bored during layovers, so he studied cartooning, since he enjoyed drawing as a boy. He was good, and after getting panels published in Air Line Pilot Magazine, True, Argosy, Saturday Review, and Sports Afield, he cracked the big time: The New Yorker. “Leo was one of the most consistently funny cartoonists we ever had,” said Robert Mankoff, the magazine’s cartoon editor. “Starting around the mid-1990s, no one was published in The New Yorker more than Leo.”
The magazine turned to Cullum for the first cartoon it ran after the 9/11 attacks (Woman in bar, speaking to a man wearing a plaid jacket: “I never thought I’d laugh again. Then I saw your jacket.”) His distinctive style, which often featured animals, was easily recognized by regular readers. Cullum retired from his pilot duties at 60, but continued cartooning for The New Yorker, which published more than 800 of his panels over 33 years. He died October 23 from cancer. He was 68.