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  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 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. 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 claims to be 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 the letter to enlarge.)

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” I submitted each month. So I knew that Hefner’s gatekeeper appreciated my indirect take when it came to male lust; she liked my gags enough to show them to her boss. Several months went by before I heard the final verdict, which you see above.

I showed the no-sale note to a feminist-Marxist friend of mine, just for laughs. She promptly displayed her sharp radical-chic sense of humor by scrawling the note in the upper right corner of the letter. Her comment alone made my efforts worthwhile.

Below are three rejected cartoons from one of the 1997 batchs of ten monthly cartoon ideas. You be the judge—are they Playboy-worthy?

To purchase reprint rights for these and many other of my cartoons, visit my archive at

Copyright © 2010 Jim Sizemore.

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.

  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.

  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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