Leo Cullum Leo Aloysius Cullum ( January 11 , 1942 – October 23 , 2010 ) was an American cartoonist , one of the more frequent contributors to " The New Yorker " with more than 800 gag cartoon s published . He started his drawing career after having served as a pilot in the United States Marine Corps during the Vietnam War and flying planes commercially for Trans World Airlines and American Airlines . Born in Newark , New Jersey , Cullum was raised in North Bergen , New Jersey and earned his undergraduate degree in 1963 from the College of the Holy Cross , where he majored in English . He joined the United States Marine Corps after graduating from college , earning a commission as a second Lieutenant . Upon completion of his flight training in Pensacola , Florida , Cullum deployed to Vietnam , where he flew more than 200 missions , mostly ground attacks in support of the infantry in addition to attacks on the Viet Cong supply lines on the Ho Chi Minh trail in Laos . Though the missions over Laos were not officially acknowledged , Cullum was baffled by the need for secrecy , saying " the North Vietnam ese certainly knew it wasn ' t the Swiss bombing them " . Early cartoons . After completing his military service , Cullum became a pilot for TWA , which was later taken over by American Airlines , where he worked until his retirement in 2001 . In between flights , he started doodling , continuing his early interest in drawing cartoons . He said , " I bought some instructional books which explained the format , and I began studying the work of various cartoonists " . He had always hoped to be published in " The New Yorker " , which turned down a series of his early entries . The magazine liked some of Cullum ' s concepts for cartoons , which were turned over to Charles Addams for illustration , with the first of Cullum ' s ideas appearing in print in 1975 showing a couple paddling in a canoe with their reflection in the water showing a vision of the man attacking the woman . Addams convinced Cullum to pursue his craft , and his first sale was to " Air Line Pilot Magazine " . He had later cartoons printed in " Argosy " , " Saturday Review " and " Sports Afield " . " The New Yorker " . Over his career with " The New Yorker " the magazine published 819 of his cartoons , many of which involved animals . His first successful entry was published on January 3 , 1977 , and featured a man wearing a robe at an office desk in a room filled with chickens . A cartoon with the caption " This island isn ' t big enough for two cliches " showed a school of fish attempting to crawl onto the shore of a desert island populated by a man and a lone palm tree . Cartoon editor Robert Mankoff called him " one of the most popular " cartoonists at " The New Yorker " during the 1980s and 1990s and " one of the most consistently funny cartoonists we ever had " . Cullum ' s was the first cartoon included in the first illustrated issue printed after the September 11 attacks , with the caption " I thought I ' d never laugh again . Then I saw your jacket . " One of his most requested cartoons features a man lecturing a cat with the caption " Never , ever , think outside the box " . His most recent cartoon appeared in the issue dated October 25 , 2010 . Books . His published books include collections about doctors and birds , with the respective punny titles of " Suture Self " and " Tequila Mockingbird " . Other books featured his cartoons about cats , dogs and business people . A resident of Malibu , California , Cullum died of cancer at the age of 68 on October 23 , 2010 , at Cedars - Sinai Medical Center in Los Angeles . He was survived by his wife , Kathy , a former flight attendant who he had met on a flight to Boston , as well as by his daughters Kaitlin Cullum and Kimberly Cullum , both of whom had been child actor s .