Playboy Or Not?

On Being Rejected By “Hef”

Back in the 1980s and ’90s, when I was trying to become a magazine cartoonist and having only moderate success at venues such as the Saturday Evening Post, TV Guide, and Writer’s Digest, the publication I really wanted to crack was Playboy. Next to the New Yorker, (which rejects just about everybody) Playboy was and is one of the highest paying magazines still in the gag cartooning game. The problem was, I had no idea how to write a sexy caption or draw a sexy woman—especially not a sexy naked woman. But the money was good, so I decided to try anyway and hope that Hugh Hefner, the magazine’s founder and editor, would find my subtle attempts at fleshy humor appealing. After all, I thought, the man’s not just a booty-hound, he’s also an intellectual—all you had to do was read his essays in the magazine to know that. But as it turned out selling him one (or more) of my cartoons was not to be. (Click once or twice on the rejection letter for a larger view.)

Prior to receiving that letter I had been encouraged when the long-time cartoon editor of Playboy, Michelle Urry, “held” some images from three “batches” of ten cartoons that I submitted each month. So I knew that Hefner’s  gatekeeper appreciated my indirect take when it came to the subject of male lust, liked them enough to show them to the boss. But several additional months went by before I heard the final verdict, which you see above. Just for laughs I showed the no-sale notification to a feminist-Marxist friend of mine. She promptly displayed her sharp radical-chic sense of humor by scrawling the note you see in the upper right hand corner of the “damning-with-faint-praise” letter. Her joke alone almost made the failed efforts worthwhile.

Below are three rejected cartoons from one 1997 batch. Now you be the judge—are they Playboy-worthy?

To purchase reprint and/or other rights for these cartoons, buy  framed prints, or have them reproduced on T-shirts, mugs, aprons, etc., visit the CartoonStock website by clicking the sidebar link.

Copyright © 2010 Jim Sizemore.
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5 Responses to Playboy Or Not?

  1. randy enos says:

    Hefner was always a little hard to sell but the fact that you actually got to him through Michelle is a feather in your cap. I think he liked your style . . . the gags were just not strong enough for him. A few more tries would have done the trick I bet. I was lucky because I drew a strip (5 Cent Mary) in a style (because of the linocuts) that reminded him of his favorite cartoonist John Held. As a result, I think I got away with murder and many an awful gag snuck through. My other strip Reg’lar Rabbit was tolerated also because I think he liked the little bugger but he did reject a lot of my ideas. Sometimes he would make a little suggestion on the rough with a little drawing (about a facial expression or a space filler where there was a blank area in the drawing)….. so, as a result, I have two original little cartoon sketches by the frustrated amateur cartoonist himself Hugh Hefner.

  2. Jim says:

    Thanks for the wonderful comment, Randy. Any chance you’ll do a blog post on your blog and show us the “Hef” sketches? I’d love to see them.

    http://www.drawger.com/bigfoot

  3. randy enos says:

    I did do a post called “Stripping for Playboy”. The drawings by Hefner are in that post I believe.

  4. Jim says:

    Randy’s right. Click the link below, scroll down to the second post on the page, and you’ll see “Hef’s” sketches. Also some beautiful examples of Randy’s Playboy comic strips.

    http://www.drawger.com/bigfoot/?start_date=1199163600&end_date=1201842000

  5. Mister Ron says:

    The art is fine. These days, the gags are probably appropriate for “Jack & Jill” or “Boys Life” :)

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