The Playboy Writer and Cartoonist
Shel wasn't quite in on the ground floor of Playboy, but he probably hit the first floor. He and Hugh Hefner had a lot in common - they both grew up in Chicago, they both served in the army, they were both cartoonists and they both loved women (more on that later). At the time, the magazine was so new that when Shel didn't hear back from Hef within a month or so of dropping his cartoons off for review, he just assumed that the fledgling magazine had gone under. When he went back to pick up his portfolio, though, Hef personally told Shel that he was buying several cartoons and forked over a check right then and there. But the check was more to Shel than just money - it represented his ability to support himself on his talent, which his dad had mercilessly mocked him about for years. He cashed Hef's check immediately, went home and threw the money down on his parents' table and told them he was moving out and was going to support himself as a cartoonist. Shel's first work for the Bunny Pages showed up in the August 1956 issue. He quickly moved from penning cartoons to doing entire travel articles where he acted as writer, photographer and illustrator; the first one appeared in the February, 1957 issue ("Return to Tokyo"). He did a whole series of travelogues and they became the second-most beloved part of the magazine (I'll let you guess what takes first place).
The Ladies' Man
It may well have been his first "real" job at Playboy that shaped his love of women, or maybe it was because he had never had much luck with girls in high school. But Shel loved women and had a voracious appetite for them. But he never lied to them - he was very straightforward that he was all about his career and just wanted to have fun flings, never a relationship. Diane Chandler, the Playmate of the Year for 1966, said Shel had a particular way of shooting down women who had gotten a little too attached to him: "He instantly saw the signs and would say something like, 'Well, let's see, where shall I put you on my list?' to let the girls know that they shouldn't expect anything from him." But for the most part, girls were OK with that. Women flocked to Shel by the hundreds and would do just about anything for him. He even had a sampler on his wall done by a Playboy Playmate. It said, "Shel Silverstein told me to make this for him."
We don't know much about Shel's relationship with his children, but we know that he had two of them (and given the rate he went through women, maybe more). His daughter, Shoshanna, was born on June 30, 1970. Because of Shel's nomadic and completely unpredictable lifestyle, she stayed with her mom, Susan Hastings. Sadly, Susan died in 1975 when Shanna was just five, but instead of Shel taking her in, Shanna went to live with her
The second, Matt, was born on November 10, 1983. His mom was Sarah Spencer, a woman who drove the conch train in Key West and inspired Shel's "The Great Conch Train Robbery" song. Shel bought a house in Key West and settled down there - at least "settled" for Shel; he still came and went - and spent much more time with Matt than he had with Shanna. Friends said that though he didn't discuss it much, one of his biggest regrets was that he hadn't been a better father to his daughter. Shel dedicated Falling Up to Matt.
It seems like creative people find one another - it has happened with countless literary groups for years, from Ernest Hemingway, Gertrude Stein and F. Scott Fitzgerald to J.R.R. Tolkien and C.S. Lewis. And it happened with Shel, who was close friends with a number of creative types - Herb Gardner, Lois Nettleton, Bob Gibson and LeRoy Neiman.
He was also very good friends with Jean Shepherd - yep, A Christmas Story Jean Shepherd, who was also published in Playboy. Shel wrote the liner notes and drew the cover for Jean's 1959 album, "Jean Shepherd and Other Foibles." He managed to sneak the words "Jean Shepherd is a dirty rotten, one-way sneaky son of a bitch" into the art by spelling it out backward. In fact, it was because of Jean that Shel wrote one of his most famous songs...
..."A Boy Named Sue." Yep, Shel was an accomplished songwriter who had several hit songs under his belt, but this one is probably the most beloved. And if you didn't know that Shel wrote the lyrics, wait until you hear it again - you'll shake your head and realize that of course he wrote those lyrics. The story goes that he was inspired to write the song after hearing Jean Shepherd frequently recall how much he got teased as a kid for having a girl's name. He also wrote Cash's "25 Minutes to Go; "Sylvia's Mother," "The Ballad of Lucy Jordan" and "The Cover of the Rolling Stone," all originally performed by Dr. Hook and the Medicine Show; "One's on the Way," performed by Loretta Lynn; and "The Unicorn" by The Irish Rovers. He didn't find it odd to switch from Playboy to children's poems to song writing - Shel believed that creative people could move about within their fields pretty easily:
“I think that if you’re truly creative, you can work in certain related fields of creativity, but then there are others that are beyond you. For instance, a man who works well with words might work as a writer and as a poet and as a lyricist. But if he tried to work in sculpture, he might get absolutely nowhere. And a guy who is very visual might easily work in painting and drawing, could also work in costume design, if he leaned that way, could work in stage setting, and in those related fields. I do believe that a person who is truly observant in one of the arts will be truly observant and sensitive in the others as well, but it’s his ability to express these things that would limit him. I believe that a man who is a sensitive painter is sensitive to life, and therefore would be sensitive as a writer or as a storyteller, but having the ability to write is something more than merely seeing. Having the ability to paint is something more than merely seeing the colors, seeking the form. It’s in execution, in skill.”