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A Puzzling Career

Robert Leighton (J82) parlayed his beloved Daily Northwestern cartoon strip Banderooge into a humorous and creative career with great puzzability.


by Cate Plys

Turns out Elaine on Seinfeld isn’t the only one who can’t figure out how the New Yorker chooses cartoons. “None of us know why they buy a cartoon,” says Robert Leighton (J82), now a regular New Yorker contributor. Of his own that the New Yorker has picked up, Leighton’s favorite pictures a mother and baby bird in a nest constructed entirely of cocktail umbrellas. The baby bird looks up at his mother and says, “Father drinks, doesn’t he?”

Leighton’s Northwestern contemporaries remember him for his Daily Northwestern comic strip Banderooge, which from 1978 to 1982 followed the title giant cat through four years of roommates, class and cafeteria hell. When Banderooge passed the cafeteria complaint board, rather than tacking up a note, he nailed dripping pieces of unidentifiable meat.

“I had two goals when I came to Northwestern: do a comic strip and start a humor magazine,” says Leighton, who co-founded the now-defunct Rubber Teeth magazine. “When I think back on college, those are the only memories I really have of what I did. I never picture myself in class.”

But it was puzzles that really led Leighton to the pages of the New Yorker. Another college humor magazine editor showed him an issue of Games magazine featuring a puzzle adapted from cartoons by renowned New Yorker contributor William Steig. “It was a revelation to me because it was partially a puzzle but to me more humor — you needed a sense of humor to figure these out,” Leighton recalls.

Games became his first job out of college, as assistant editor. There Leighton got to work with “the very best people” in the puzzle business, including Will Shortz, now crossword editor of the New York Times. Leighton stayed for five years before going freelance, diversifying into TV writing at Nickelodeon and Comedy Central and beginning a puzzle-writing company, Puzzability, with two partners. Puzzability is based in New York City, where Leighton lives with his wife and son.

In 2002 New Yorker cartoon editor Bob Mankoff wanted a new approach for the magazine’s annual cartoon issue. Mankoff called his friend Shortz to ask if he knew anyone who could work cartoons into puzzles, and Leighton made his first trip to the New Yorker’s offices.

Now, every week Leighton and about 30 other cartoonists gather outside Mankoff’s New Yorker office and wait their turns to show him 10 or so cartoons, never knowing which may be the chosen ones. “Part of the reason I like doing it is I just like being part of that group,” Leighton readily admits. “The New Yorker cartoonists are among my set of heroes.”

This spring for Father’s Day, Black Dog & Leventhal will publish The New Yorker Book of Cartoon Puzzles and Games, created by Puzzability using the New Yorker’s complete catalog of cartoons. “I think a puzzle is like a cartoon, like a joke, because the puzzle is the setup and the solution is the punch line,” says Leighton. “A good puzzle keeps you in suspense while you’re working on it, like a cartoon. And the ‘aha!’ is the equivalent of the laugh when a joke is resolved.”

Two Leighton cartoons made it into the New Yorker’s complete cartoon collection published in 2004 — even though only about 2,000 cartoons fit into the actual book. Leighton still can’t quite believe it himself, since his New Yorker contributions had just begun in 2002. “It made me feel like Indiana Jones,” he says, “snatching his hat out from under that giant door at the last second before it slammed shut.”

Cate Plys (J84), a Chicago writer, still has a picture of Robert Leighton in drag from a 1981 Halloween party. He’s lucky she couldn’t find it before deadline.
Robert Leighton in his Northwestern Banderooge days
Robert Leighton in his Northwestern Banderooge days Photo by Barb Jarrow
Robert Leighton with New Yorker cartoon editor Bob Mankoff, center, and New York Times crossword editor Will Shortz
Robert Leighton with New Yorker cartoon editor Bob Mankoff, center, and New York Times crossword editor Will Shortz Photo by Laura Ross