Robert: Hef! [laughs] There's a great documentary somebody did in 1966 when he was at the peak of his empire — he had the Playboy magazine, which was hugely popular, and the Playboy Clubs going and he was writing this Playboy philosophy — so somebody did this documentary about him. And they weren't out criticize him or anything, they just wanted to show his whole scene. And the interviewer asked him, "Mr. Hefner, would you consider yourself a genius?" And Hefner is smoking his pipe, he reflects for a couple of seconds and then he takes his pipe out of his mouth and says, "Yeah, I guess I would consider myself a genius." [laughs]. But Hefner... a very cornball guy. Yeah, I guess he had kind of a publishing genius, in that way he was kind of. But he was so Midwestern. And what he did to Kurtzman, I can never forgive him. You know, when Kurtman left Mad magazine and then Humbug was a failure, he was desperately doing these comic strips for these little magazines like Pageant and Coronet and stuff like that. And Hefner liked his work. And I don't know if he solicited Kurtzman or how exactly it worked, but Denis Kitchen has these exchange of letters between Hefner and Kurtzman where Kurtzman is trying to submit ideas for Playboy. And Hefner's writing back these criticisms that are so demoralizing. Omigod, it was so terrible what he was doing. He knows he's got Kurtzman on a string, you know? And he's just dangling him on a string. And it was so demoralizing for Kurtzman to work for Hefner. I remember once being in Kurtzman's house and he was working on this Little Annie Fannie strip for Hefner. Kurtzman showed me these things he's gotten back from Hefner, because he had to send, with every strip, these roughs of the strip for Hefner's approval. And Hefner would send back the roughs with a piece of tracing paper over each of the roughs with these little knit-picky blue pencil changes he wanted made. So Kurtzman showed me these, and he'd been drinking a little, and he just started weeping with vexation, literally weeping. He said, "Look at this. Look at what I have to endure with Hefner. Okay, I'm grateful to the man, he rescued me from poverty." Kurtzman had a big house and he had an autistic son that cost a lot of money to take care of, so he needed the money. So he did that Annie Fanny strip. But, what he had to endure from Hefner. That always pissed me off about Hefner. I met Hefner a couple of times. Kurtzman took me and Jay Lynch and his wife Jane Lynch and Skip Williamson to the Playboy mansion when it was still in Chicago. And Kurtzman was very worried about us offending Mr. Hefner. And he told us before we went in, "Please you guys, don't do anything outrageous, Okay? Please don't offend Mr. Hefner." [laughs] So Skip Williamson, who was, at that time, a very rebellious young man, deliberately acted rude and crude, so he didn't get invited back.
Once I got well known in the hippie community, '69 or '70 or something like that, Hefner sent his cartoon editor Michelle Altman to ask me to contribute to Playboy. But I turned it down because I knew what I'd have to go through with Hefner.
Alex: It's not like you had political grievances with Playboy, but more because you didn't want to go through the hassle with Hefner?
Robert: Well, I did have political criticisms of it. I did. And the money was tempting. It was top money at the time. But I just knew I wouldn't have that freedom. Hefner's not going to give you the freedom. Money wasn't that important to me then. I was pretty foot-loose, and you could live pretty cheaply back then. I didn't see any need for great sums of money. In the underground, there was such total freedom, that I was spoiled by that. Yeah, it was really about freedom. I just couldn't bend myself to those guys. Those guys were so far removed from everything that we had gone through in the hippie culture. That generation, of Hefner and all those middle-aged business people, when they approach you and try and get you to work for them, they're just trying to cash in on the hippie thing. They're trying to cash in and capitalize on that new youth market. And they're so out of it. They just didn't get it. Hefner didn't get it. Kurtzman didn't get it! [laughs] Kurtzman came closer to getting it than Hefner. After Playboy became successful, Hefner had become shielded from the world inside his Playboy mansion, so he was in his own little world that he created. I don't think he really knew what was going on outside the mansion.
The Playboy mansion was a very weird place. I went to this party there with Kurtzman, this cocktail party one night. And it was so stifling. Everybody's behavior was so stilted, and the drinking and, those kind of hedonistic, materialistic guys from the WWII generation. And those bunnies in the rabbit custom? I thought it was grotesque. [laughs] Jane Lynch, already in her feminist stage by the time of the party, confronted these Playboy bunnies. She was like, "How can you bear the humiliation of wearing those costumes, that stupid collar with that tail and those ears?" Of course the bunnies were very offended. They had already made the decision to accept the whole thing for the money and here's this girl telling them it's stupid looking. One bunny just looked at her and said, "You know, the money is really good, Sweetie. It pays well." [laughs] But it was a repellent scene. Sid Caesar, I mean, he was completely out of his mind, just babbling. And these other guys who were there, older guys, they said, "Yeah, Sid Caesar's crazy, just crazy." Yeah, there were a lot of characters around there, but the atmosphere was so stiff and stilted. Even though it was supposed to be all fun and hedonistic and loose sex, it just wasn't like that, at least not for me. Kurtzman used to stay in the mansion in Chicago, and the first thing Hefner would say to him in the morning was, "Hey Harvey, ya get any last night?" Yeah, the girls were there, they were there for the picking, but you had to work at it. You had to be able to charm them.