Here’s a memory about Playboy Magazine, from our brilliant cartoonist, Randy Enos.
About 6 years into my tenure at Playboy magazine, they decided to start a comic strip section in the back pages. They already had a strip called Little Annie Fanny by Harvey Kurtzman that had been running for a while and they were keeping that separate from the “Playboy Funnies” which was to be the name of this new feature. 
They asked me to think of an idea for a strip. They said I could even have a couple of strips if I wanted, so, I started working on some ideas. The first thing that appealed to me was the idea of maybe doing an “old fashioned” looking strip, perhaps modeled after some of my favorites like “Polly And Her Pals” by the great Cliff Sterrett or Harry Hershfield’s, “Abie the Agent”. I tried a few of these amounting to about half a dozen samples and Hugh Hefner picked two. They would alternate, one in each issue.
The first one which I called “5 Cent Mary” derived its moniker from a person I knew of from my youth in New Bedford, Massachusetts. She was a legendary prostitute who worked the fishing piers and dives down in the cobblestoned streets of the city’s wharves. I actually met her once when my father and I were in a diner very early in the morning having breakfast before going fishing. For some reason, I don’t remember how, I knew who she was… maybe my father told me later. Anyway, she sat down beside me and said, “Haven’t I seen you in church?” I think I told her that I didn’t go to church. That was my brief encounter with the famous “5 Cent Mary.” I wish she could have known that I memorialized her in a Playboy comic strip. She probably would have enjoyed that.
I decided that my “5 Cent Mary” would be a street hooker of the late 1800’s and that I would do it in linocut (the medium that I used for my illustrations) to give it a different look than all the other strips. Hefner loved it. Unbeknownst to me, his favorite cartoonist was John Held Jr. and, while I knew little of Held’s work at the time and hadn’t even thought about him when I created Mary, if you do a cartoon in linocut and you draw it in 19thcentury setting and costuming – BINGO, you get a John Held looking comic strip whether you like it or not! Hefner agreed with me that it should be the only strip in the Funnies section in black and white. He always loved it even when I had some pretty bad gags.
The other cartoon he picked was “Reg’lar Rabbit”. My character was a horny little Farmer Brown-type of country hick who was always chasing the ladies. Reg’lar was drawn in a simple conventional pen and ink style with the addition of adhesive color. Doing “Reg’lar” was a nice break in my normal lino-cut illustration activity for the next 6 years.
A wonderful woman named Michelle Urry (who died young, unfortunately) was much beloved by the Playboy cartoonists’ community and was our contact with Playboy in the New York office. The strips and the gag cartoons for the magazine were collected up by her and taken to Chicago once a month where she would go over everything with Hef, who was always the final word on cartoons. On two occasions, he scribbled a little suggestion for me. One was for “Reg’lar Rabbit” where he drew a suggested expression for the rabbit and the other was on Mary where he suggested a little figure to fill an awkward space I had left in one panel. I’ve kept these crude little “notes” all these years. After all, how many people have an original Hugh Hefner cartoon?
Some of the other cartoonists that did strips included Bobby London, Chris Browne, Art Spielgelman, Lou Brooks, Jay Lynch, Mort Gerberg and more..
One year, we cartoonists were all invited to a special Playboy cartoonists’ party at the Drake Hotel in New York. I first met my long-time friend Elwood Smith at that party. As the evening wore on and the drinking accelerated to a spectacular pace, an odd thing happened in a side room in the suite. Michelle Urry had gone in there and came out screaming, “Are you all crazy… what is wrong with you???”
Well, I hadn’t been in that room so I rushed in to see what it was all about, and there my eyes beheld an amazing sight. All over the smooth, pristine, pale, muted walls of the sedate hotel room, several cartoonists had profusely, and I mean PROFUSELY scribbled cartoons with ball-point pens.
Some of them were pretty darn good, too!
Read more more of Randy’s cartooning memories:
Art School Days in the Whorehouse
The Card Trick that Caused a Divorce
8th Grade and Harold von Schmidt
The Funniest Man I’ve Ever Known
Read “I’m Your Bunny, Wanda –Part One”
Read “I’m Your Bunny, Wanda –Part Two”
Famous Artists Visit the Famous Artists School
Randy and the National Lampoon
Randy Remembers the National Cartoonists Society
Later in life, I visited the New York club which was glitzy, full of big windows and flash whereas this Chicago club was simpler and homier. The famous Playboy bunnies were flitting about everywhere as we entered and we were shown to a table in a large room with a stage. Art said we were going to see a show while we ate. It turned out to be a standup comic.
Art: “No no no, you don’t pay for anything while you’re here.”