Drafted into the United States Marine Corps in 1944, he was invited to re-enlist and join the Corps' Leatherneck magazine as a staff cartoonist; when re-drafted for the Korean War, he was ordered back to Leatherneck. As a civilian, he moved to New York City where he struggled as an artist, married, then worked as an art director in the magazine world. During this era he worked on the comic strip Spot in 1956. Fed up, he quit and pursued cartooning full time, beginning a successful phase in 1969 with his first New Yorker cartoon sale. He also created the comic strip Local Item in 1986.
Over time, his cartoons have become an iconic feature of the magazine. In a doodler's style, they feature everymen beset by modern complexity, goofballs perplexing their spouses, cats, and very often a fat dog. One signature element is a ceiling light bulb on a cord pulled out of vertical by another cord attached to an electrical appliance such as a toaster. Most of the household features in his cartoons are taken from his own home, such as the rugs, chairs, ferns, and cats.