Not much is known about Caldwell's early days. Rumors of his once being a carnival dunk tank clown remain just that -- unsubstantiated rumors. There is documentation, however, that he did spend parts of 1969 and 1970 working for the State of New York as a cartographer. In a less than distinguished career marred by careless mistakes, an inability to tell north from east and the outright invention of imaginary highways and byways, he left a folded paper trail of infamy. A tissue of unchartable lies. Indeed, you might still find an occasional topographic map of New York showing roads that never existed bearing names like HEY, IT'S ME JOHNNY AVENUE and HOW BORING IS THIS BOULEVARD. There's even a IF I LIVED HERE THIS WOULD BE CALDWELL LANE just north of Rochester.
Realizing, under pressure from supervisors, that drawing maps was not the creative outlet he'd imagined it to be, Caldwell moved on to cartooning, an even more tenuous means of expression.
Nevertheless, over the years, his drawings have appeared in many publications, including The National Lampoon, Writer's Digest, Playboy, Barron's, The New Yorker, The Wall Street Journal, Reader's Digest and Harvard Business Review. He also appears regularly in and is proud to be one of the Usual Gang of Idiots at Mad Magazine.
His books include one children's book, several collections of his own cartoons, and a 1991 work titled FAX THIS BOOK, which did for the sale of fax machines what CHICKEN SOUP FOR THE SOUL did for VCR repair.
Caldwell also designs greeting cards for Recycled Paper Greetings and Nobleworks.
He lives with his wife Diane and dog Jade in upstate New York on a real road named by someone other than himself.