Retro Heaven

The Artist Shel Silverstein

The Playboy cartoons of Shel Silverstein…


Shel Silverstein led a remarkable life. Born in Chicago in 1930 he would go on to become a poet, a singer-songwriter, children’s author, cartoonist and screenwriter. His books sold more than twenty million copies in thirty languages, he wrote most of Dr. Hook’s songs including the worldwide hit, ‘Sylvia’s Mother’ and the classic Johnny Cash hit ‘A Boy Named Sue’.

In 1957 he got his first real break as cartoonist at large for Playboy. A dream job, he was sent around the world with his sketch pad documenting life in amusing cartoons from Moscow to Paris, to Mexico, London and Spain amongst other places. His cartoons and observations often led to two and three page features in the magazine and offered a charming insight into faraway places in a pre-internet era.

The features often showed photographs of Silverstein at work, sketching scenes whilst being watched by locals, tourists and the odd Soviet policeman! Accompanying the sketches were harmless, humorous digs at the country and its people as well as Americans and especially American tourists. Silverstein quickly understood the place he was visiting and the locals perceptions about Americans and wasn’t afraid to show it and often used his own self-portraits as the butt of the joke. The cartoons were eventually published in one volume in 2007 called ‘Silverstein Around the World’

He was a regular contributor of ‘one-off’ cartoons to Playboy too, from the fifties until the mid seventies there was seldom a copy which didn’t contain his artwork alongside other cartoonists who were usually somewhat closer to the mark than Silverstein would allow himself to go.


By the 1980s his output had slowed somewhat but by the beginning of the 90s he had published more work before his death of a sudden heart attack in Florida in 1999. Below are some examples of Silverstein’s travels to Moscow and Paris for Playboy magazine.

Artwork copyright Shel Silverstein for Playboy magazine.

























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