Playboy founder Hugh Hefner passed away on Wednesday at the age of 91 and in his passing, the comics world lost one of their greatest benefactors. Hefner was a lifelong admirer of comics and went out of his way to not only feature many comics in the pages of Playboy for over 50 years, but he also put his money where his mouth was in his support of comic artists, as the rates he paid were unheard of at the time.

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Almost assuredly, the reason that Hefner was so into comics was that he, himself, was a comic book artist when he was growing up. While Hefner was in high school, he kept a comic book diary about his life. He had already begun to cultivate a personality for himself, referring to himself as "Hef" even back then...

In many ways, those early Hefner comic books were much like the prototypes for Playboy, as Hefner would work in little other bits of odds and ends into his comics and turned them into, in effect, a scrapbook for his friends and family to read.

When Hefner attended the University of Illinois, he also founded a magazine that was similar to what Playboy would eventually become, including Co-Eds of the Month (clothed, though). Hefner would contribute gag cartoons to the magazine. Hefner even released a book of gag cartoons in 1951, a couple of years before founding Playboy...

Once he founded Playboy, Hefner was intent on heavily featuring comics within the magazine. Geoff Boucher spoke to Hefner a number of years back about Hefner's favorite artists growing up, and he explained how his fandom led to him getting one of the most famous comic artists in the world to contribute to Playboy's second issue ever! "Milton Caniff first and foremost. I actually got got Caniff for Playboy. During World War II, Caniff did a comic strip called Male Call with a very sexy lady named Miss Lace; it was in ‘Stars & Stripes‘ and ‘Yank’, and it was for the service guys. I knew that some of them had been rejected for being too sexy. So when I started Playboy in summer of 1953, I wrote to Caniff and asked if I could reprint some of the strips, and I asked whether he would supply me with the ones that had been censored and not printed. Those appear in the second issue of Playboy. So my idol, for no particular reason, said yes to a kid that had this impossible dream and was puttering together the first issue of Playboy with literally just $8,000 and no hope."

Another one of Hefner's favorite artists growing up was the legendary Jack Cole, creator and longtime artist on Plastic Man. Cole had moved into cartooning as the 1950s began and Hefner quickly made him one of his regular artists and Cole's work for Playboy was magnificent. Here's a stunning Valentine's Day piece Cole did for the magazine...

Cole worked for Playboy until his suicide in 1958. He was eternally grateful to Hefner for giving him the gig. Cole left only two suicide notes. One for his wife and one for Hefner.

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Another artist that Hefner greatly admired was Harvey Kurtzman, one of the most accomplished comic book creators of the 1950s. Kurtzman launched Mad for EC Comics. Kurtzman believed that the magazine was good enough that he forced EC to turn it into a magazine rather than a comic book after a number of issues. That inadvertently kept it from running afoul of the Comics Code a few years later and it allowed EC Comics to remain in business. Eventually, though, Kurtzman and Gaines had too many disagreements so Kurtzman was wooed by Hefner to launch a version of Mad for Hefner's Playboy Enterprises. Kurtzman agreed and brought Jack Davis and and Will Elder with him.

The resulting magazine, Trump, was excellent, but it came out at a poor time for Hefner, as the magazine cost a lot to produce (Hefner once joked that he had given Kurtzman an unlimited budget and Kurtzman somehow found a way to exceed it) and Hefner was a bit cash poor at this particular point in his career, so he had to cut back on his attempts to expand his magazine line. So Trump was canceled. Hefner felt awful about it, so he let Kurtzman keep the office space for free to develop other ventures (note that he didn't feel so awful that he forgave the advances he had paid all of the artists - he made them work off any advance money on gag cartoons for Playboy). Kurtzman and his Trump artists then launched a self-financed magazine, Humbug, which totally bombed.

Kurtzman, then, struggled for a few years before convincing Hefner to adapt Kurtzman's parody of Archie Andrews into a parody of Little Orphan Annie called Little Annie Fanny. Kurtzman would do the strip with Will Elder and a number of other old Trump and EC artists, like Russ Heath and Frank Frazzetta.

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Here, though, is where the dark side of Hefner's love for comics came in. While Hefner loved these cartoonists and paid them handsomely, he was also beyond meticulous with them. He was almost abusive in how many changes he would force on Kurtzman on each strip. We're not even talking about forcing Kurtzman to dumb the strip down to make it more lacivious, which Hefner certainly did do, but we mean just hundreds of minor little corrections ("Move that table," "Change that guy's shirt"). It was because Hefner respected Kurtzman so much that he paid so much attention to Kurtzman's work, but the end result was practically harassment. The artists all respected Hefner's views as a comic book editor in general, but in specific, it was just way too much input. John Kelly had an excellent article a couple of years back at The Comics Journal about Hefner's micromangeing. Well worth a read. As Kelly notes, Kurtzman owed a lot to Hefner and was very grateful (Hefner even kept Kurtzman on the Playboy medical plan after Kurtzman stopped doing Little Annie Fanny in 1988), but he was also highly frustrated over the working arrangements.

Playboy employed a number of other notable cartoonists over the years, including Shel Sliverstein...

Gahan Wilson...

Buck Brown and his Granny character (this pin is the only Granny one I've seen without nudity)...

and Doug Sneyd...

Sadly, Playboy decided to cease having cartoons in their magazines in 2016, at the same time that they decided to no longer have nude women appear in the magazine. Hefner was just about ready to step down as the publisher of Playboy and he did not like either idea, but he was convinced otherwise (he fought harder on the comics change than the nudity change) Hefner's son then overturned the nudity ban in 2017, but the cartoon ban remains in place (Hefner stepped down as the publisher of Playboy in October 2016).

Oh, and just for fun, here's the full version of the Stan Lee/Hugh Hefner photo together...