It was at Holy Cross that Cullum decided to become a pilot. The draft was on, and he talked to a school adviser about ways of fulfilling his military obligation. The counselor told him that the Air Force was looking for pilots. “Sign me up,” Cullum told him.
He later switched from the Air Force ROTC program to the Marine Corps Platoon Leaders Class, since the Marines let him complete his training during the summer. After graduation, Cullum was commissioned a Marine Corps second lieutenant. While awaiting orders, he took up his regular summer job driving a beer truck to the bars around Greenwich Village; in August, Cullum received orders to begin flight training in Pensacola, Fla.
“It was quite a transition from the rigors of Holy Cross to the beaches of the Gulf Coast, with a nice car, a regular paycheck, and the excitement of learning to fly,” he says. After taking advanced jet training on the F-4B Phantom and learning to take off from and land on aircraft carriers, Cullum received his wings.
By April 1966 he was in Vietnam. He was based in Da Nang and later at Chu Lai—and was amazed to discover in his small squadron three Holy Cross graduates: pilot James J. “Jim” Morin ’62, Naval Flight Officer Jonathan “Skip” Greenfield ’62 and Cullum’s own “back-seater” Kevin Rick ’64.
He eventually flew 200 missions, mostly in support of ground troops, but there were also flights over North Vietnam and nighttime missions code-named “Steel Tiger” over Laos, to attack the Ho Chi Minh Trail. These missions were supposedly kept secret in the States, since they would be perceived as an expansion of the war. There were, however, few secrets to those in the theater of war.
“Who these were secret from I’m still not sure,” Cullum says. “The North Vietnamese certainly knew it wasn’t the Swiss bombing them.”
He left active duty in 1968—the same year he was hired by TWA. “At the time, TWA and Pan Am were the only airlines flying international,” he says, “and that’s where I wanted to go—even though I wound up flying a lot of domestic flights also.”
Finding he had plenty of spare time between flights and during layovers, Cullum revived his old interest in art. He took a couple of painting classes and developed an interest in cartooning.
“It looked like something I could do,” he says. “I bought some instructional books which explained the format, and I began studying the work of various cartoonists.”
At that time Manhattan was the Mecca of cartooning, and every Wednesday Cullum and other cartoonists, both neophyte and established, would make the pilgrimage to those cartoon editors who traditionally held an open house that day.
“The first time I drew a batch of cartoons and took them to the city, I met a number of the artists I had been studying,” Cullum says. “It was enormous fun for me, and, though I didn’t sell anything, I did receive some encouragement from some editors. I was hooked.”
In 1973, TWA transferred Cullum to Los Angeles. He took up residence in Malibu and continued to draw cartoons when he wasn’t flying.
“I think what I loved about trying to create a cartoon was the writing at least as much as the drawing,” Cullum says. “Trying to think of a funny or pithy comment came naturally to me and here was a chance to put it to use.”
Soon he was actually selling cartoons. His first was to Air Line Pilot Magazine. Cullum’s cartoons also showed up in True, Argosy, The Saturday Evening Post and Sports Afield.
“It didn’t take long to realize that, both in terms of prestige and money. the place to be was The New Yorker,” he says. “At that time The New Yorker used gag writers, and, though my drawings were rejected on a weekly basis, they eventually started buying some of my ideas and pairing me with Charles Addams.”
In 1977, the magazine bought one of Cullum’s cartoons, and pretty soon he was a regular.
“The New Yorker, did not, as is widely supposed, invent the magazine cartoon,” Mankoff says, “but, between the late 1920s and the mid 1930s, it certainly perfected it and made it part of American and, then, world culture. We’re proud of that tradition and intend to maintain it. As long as we have cartoonists like Leo Cullum, I don’t think we’ll have anything to worry about.”
Cullum was recognized internationally in 1995 as one of three American cartoonists chosen to have their drawings published on stamps by the United Kingdom’s Royal Mail. He and his wife, Kathy, flew to London for the unveiling ceremony.
After retiring, Cullum found time to assemble and publish collections of his cartoons. First came Scotch and Toilet Water, a book of cartoons about his more-human-than-human dogs—followed by Tequila Mockingbird, which included a menagerie of beasts and humans, often in trans-species discourse—and, finally, Cockatiels for Two, a book of laughs for the cat-lover (lovers of cockatiels might not find the volume amusing). He has also moved into advertising illustration, all the while continuing to feed cartoons to The New Yorker.
And while Cullum has made his name as a cartoonist for this famous magazine, his work for the publication has never fit the New Yorker cartoon stereotype of being “hard to get.”
“Everyone gets Leo’s cartoons,” Mankoff says, “and most people—including, I might add, the present editor of the magazine, David Remnick—love them.”
The Cullums’ Malibu Mediterranean-style home is about a mile from the Pacific coast. Palms and fruit trees provide shade from the California sun, and right now the walls and terraces are crimson with tumbling cataracts of bougainvillea. Cullum’s plans for the future include enjoying warm weather, giving an occasional talk on his art at a local school and, of course, cartooning. As far as The New Yorker is concerned, that’s fine.
“Leo is one of the great cartoonists at The New Yorker,” Mankoff says. “He has done some of the great gag cartoons of all time. We love him and respect him, and we’ll keep publishing his cartoons as long as he keeps drawing them.”
James Dempsey was a columnist for The Evening Gazette and The Telegram & Gazette for 18 years. The winner of awards from the Associated Press and United Press International, he now teaches writing, journalism and literature at Worcester Polytechnic Institute and ClarkUniversity.
A Life in the Air