About a year before the first issue of Playboy, I was standing on the Michigan Avenue bridge, looking out at the river, a bit teary-eyed, thinking, “Where is my life going?” I’d recently attended a high school alumni revue that reminded me of all of the good times I had as a kid. I’d been a real school leader and done all sorts of creative things—shows and musicals. But I had put all of those dreams away. In the weeks that followed, I simply decided, ''F**k it! I’m going to create the magazine I want to create no matter what.'' And I did.
I wrote a letter to many of the newsdealers throughout the country, telling them about this wonderful new magazine I was creating. I told them that a few guys from Esquire (I had worked in the circulation department) had stayed behind in Chicago when it moved to New York. Well, the only guy who stayed behind was me. The staff was essentially my typewriter, a table, and myself.
I needed a gimmick for the first issue. The new 3-D movies were popular, so I shot a nude 3-D pictorial. Then I discovered how expensive it would be to include the necessary3-D glasses in every issue. Just as I received that disappointment, I read that a local calendar company not far from where I grew up on the West Side owned the famous nude photo of Marilyn Monroe. At the time, no one had seen it because the post office considered it obscene and wouldn’t allow it to be mailed. But I talked the owner into letting me publish the picture in the first issue of Playboy for $500. That was my very best day.
As impossible as it all seemed, once I started doing it, I was supremely, irrationally confident. I felt as if Playboy had been meant to happen, and I was energized in a way that I can’t begin to describe.
I drove out to Rochelle, Illinois, and watched the first issues come off the press, editing copy throughout the night. It was unbelievable. I came home in the morning with the first copy of the magazine, and immediately had Millie (my wife at the time) shoot a picture of me holding it.
Our first office was at 11 East Superior, two blocks west of Michigan Avenue and across the street from Holy Name Cathedral. The nuns would walk by everyday. During the first year, the cops would ticket our cars excessively and never ticket the cardinals’ and nuns’ cars. Back in those days, Chicago was a wonderful but strange city that was closely connected to the church and the mob. And we were outsiders.
When I was a kid growing up on the West Side, I could see the beacon atop the Palmolive Building from my house. That light carried tremendous iconic meaning for me—at the time, the building was the only skyscraper north of the river. In the sixties, when it became— quite rightly—the Playboy Building, I was working and living at the Chicago mansion so much that I almost never went there. In fact, the first time I visited, the night watchman wouldn’t let me in because he didn’t recognize me.
In that period, many great television shows and magazines started in Chicago and then, when they became popular, left for New York or Los Angeles. I resented that. There was so much untapped talent here. It would’ve been difficult to create the magazine anywhere else.
Eighty percent of the first issue sold, which was extraordinary. The second issue—without Marilyn—sold more copies still. And the third issue sold even better. That’s the only reason I’m here today.
