Hef in Art

By Rob. Walton

Before he became the world's most recognized publisher, Hef aspired to be a cartoonist. In the service, he drew cartoons for various Army newspapers. Hef even took art classes at the Chicago Art Institute before enrolling at the University of Illinois in Champaign/Urbana where he drew cartoons for the Daily Illini.


Following college, Hef tried his hand at cartooning and, failing to sell any of his ideas for a cartoon strip, published a book of satirical cartoons about Chicago titled That Toddlin' Town. Since then, Hef's magazines have provided a forum for some of the greatest contemporary artists, from Andy Warhol to Salvador Dali. Occasionally, some of the world's most distinctive artists, illustrators and cartoonists have immortalized Hef in ink. Here's a sampling of Hef in art.
Cartoon Photo by Elayne Lodge

Al Hirschfeld

Hef, as conceived by distinguished New York Times caricaturist Al Hirschfeld. The number three after Hirschfeld's signature indicates that Hirschfeld's daughter's name, Nina, appears hidden in the line drawing three times.
credit: © Al Hirschfeld.


Ed Sorel

   Acclaimed political cartoonist Ed Sorel, recently honored with an exhibit at the National Portrait Gallery in Washington, depicts Hef as Greek god Pan. This painting was used on the invitation to the 1985 Midsummer Night's Dream party.
credit: Ed Sorel


Matt Groening

   This animation cel from Matt Groening's Fox show The Simpsons depicts Hef as he appeared in a 1993 episode titled "Krusty Gets Kancelled."
credit: Matt Groening/The Simpsons ™&©1999 20th Century Fox Film Corp. All rights reserved.


Lenn Redman

   World famous animator and caricaturist Lenn Redman (Walt Disney's Fantasia; the What Am I? series of books) created this line drawing for Hef in 1962.
credit: Lenn Redman


Herb Davidson

   This photograph-like painting of Hef from 1970 hangs in the climate-controlled vault of Playboy's photo library.
credit: Davidson



    Internationally renowned pop artist Marisol created the six-foot-tall wood sculpture-painting for the March 3, 1967 cover of Time magazine. Note that it is painted a patriotic red, white and blue, and that Hef has two pipes.
credit: Frank Lerner


Shel Silverstein

   Children's author Shel Silverstein (Where the Sidewalk Ends) drew on his inside knowledge of life at the Mansion to have some fun with Hef in a series of cleverly captioned cartoons, published as "Silverstein's History of Playboy" in the February and March 1964 issues.
credit: Shel Silverstein

"I don't understand you -- you spend $500,000 on a house, you spend $100,000 on an indoor swimming pool, and you're too cheap to buy a few $10 bathing suits."

Skip Williamson

   Underground comix legend Skip Williamson, a contemporary of R. Crumb and Jay Lynch, created this cartoon for Hef at the commission of Playboy CEO Christie Hefner.
credit: Skip Williamson


Allison Lefcort

   A Warholesque multimedia painting of Hef on gold background by Florida's Allison Lefcort, known for her original acrylic pop-art portraits of Hollywood celebrities .
credit: Allison Lefcort


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