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Shel Game

by Brad Holland

October 17, 2000

Shel Silverstein and I had never met. I lived in New York. He had homes all over the place and lived where the vibes were best. But he was in Chicago for awhile, talking to his pals at Playboy. Kerig Pope introduced us over the phone.

In that summer of 1978, Kerig had assigned me to illustrate The Devil & Billy Markham. This was the first of several children's stories for adults which Shel was writing in comic verse and which Playboy was to publish over a period of years.

We began working as you usually do with a magazine. Shel sent his rhymes to Playboy, Playboy sent the rhymes to me, and I sent pictures to Playboy. It was simple enough. But as the series developed and Shel conjured up fictional adventures for the likes of "Uncle Don" and "Gimmesome Roy", he contrived to streamline the creative machinery of our relationship as well.

One day he phoned from somewhere in the continental forty-eight. He had been thinking, he said. The magazine had too many chiefs these days. It wasn't like the old times with Hefner on Ohio Street. He suggested that we simplify things. What if he started sending his manuscripts directly to me? We could collaborate "like Rogers & Hammerstein," cut out the editors and art directors, and I could send the finished goodies to Playboy after we had satisfied ourselves.

The idea appealed to me. No chiefs--only Indians--always appeals to you when you're an Indian. Besides, I was convinced that Shel's close friendship with Hefner, his long association with the magazine, and his general beatnik geniality would let him get away with whatever he wanted. "OK, Hammerstein," I told him, "meet Mr. Rodgers."

Shel said he could tell we'd work well together. But there was a catch: He had a hard time with the suits at the magazine. He thought he made them nervous. So he asked me to phone the art directors and relay to the editors the news that he and I were now a team. I was to say I didn't know where Shel was calling from (this was true enough). I was to say I didn't know how to find him (right). Then I was to explain the deal. He'd send his verses to me. I'd pick the ones I liked. Then when I was good and ready I'd send the words and pictures to Playboy. In effect, I was supposed to let the editors know that I was now Shel's editor and he was my art director (!). This would be touchy, he admitted, but he was sure the suits wouldn't freak out too much. They knew they could trust us. Even better, anxiety would make them grateful for whatever we finally sent them.

"What am I doing?" I thought, the next day as I phoned Kerig Pope in Chicago. It was Shel Silverstein who partied with Hefner, Shel who was a living Playboy legend, Shel who I had seen cavorting in the magazine when I was still in high school back in Ohio and sneaking my father's Playboys into the barn. Why was I playing mouthpiece for him?

Nobody at Playboy ever told me what they thought of this hare-brained scheme, more Gilbert & Sullivan than Rodgers & Hammerstein. But it didn't take long for Kerig to flip me, deputize me, and give me my counter-instructions. I was to contact Shel if I could, meet him if possible, humor him, and get the manuscripts away from him. Kerig assured me that Shel would hand them over like a pussycat. Then I was to send the verses to headquarters and we could all dispense with the monkey business.

I had found Shel to be a genuinely sweet man. But sending me to con him out of his manuscripts was like sending a rookie cop to deliver a wily jailbird to the state pen.

I tried to phone him at the numbers he had given me. He had an apartment on Hudson Street in New York, a lair in Chicago, a house in Key West, and a houseboat in Sausilito. He wasn't at any of them and there were no answering machines. I realized that Rodgers would have to run on Hammerstein Time. So I waited and went about my business. Then one day I answered the phone and heard the familiar, good-natured croak.

"Where are you?" I asked.

"I'm staying at Hef's."

"The people at Playboy are looking everywhere for you."

"They'll never find me here."

Shel said he had been writing. He had lots of stuff. It was important that we meet soon. I should come to LA. He'd need me for a week. We could work at the Mansion. There'd be lots of parties. Then he'd lay the manuscripts on me. How soon could I leave?

How soon can you send me tickets? I asked. I couldn't believe what was happening. What had started as a normal day for me had suddenly yielded the promise of a young man's fantasy come true. I saw myself winging my way out to Xanadu-on-the-Pacific. Drinking margaritas in the jacuzzi with Playmates. Playing Donkey Kong with Hefner. But then I remembered I had just met the girl of my dreams. I told Shel I wanted to bring her.

He paused. "Let me get this straight," he said. "You want to bring your own girl to the Playboy Mansion? Have you ever heard of 'coals to Newcastle?'" Shel took a few minutes to make sure I understood the difference between sex and love. "I'll bet your girlfriend's a country girl," he said. "I'll bet she stares. You shouldn't be with a woman who stares."

But Shel made the arrangements and within a week Judy and I were settled into the Beverly Hilton Hotel and driving to the Playboy Mansion as matter-of-factly as if we were going to grandma's at Christmas.

It was late morning, but the Mansion was still. Shel met us at the door dressed in a striped floor-length caftan and sandals. The house was alive with hushed activity, as my grandparents' house used to be when grandpa worked nights and slept mornings.

We sipped orange juice in Hefner's living room as servants vacuumed and emptied ashtrays from the night before. Shel had a pile of manuscripts neatly typed with interlineations: The Perfect High, California C's, Rosalie's Good Eats Cafe. We went through them. They read like country western ballads without music.

As my girlfriend drew crested cranes in her sketchbook and grew sunburned on the lawn of the Mansion, Shel and I went over his verses, line by line. It surprised me to discover that his Dharma Bum demeanor masked the concern of a schoolmarm that people "get" the point of his stories. Over the next two years I would see this concern for the transparency of his comic verse repeated as we met for editorial pow-wows in Greenwich Village laundromats, at the Caffe Dante on Macdougal Street, at Washington Square park at high noon, or on various midnight street corners, in the company of women I didn't know and who I doubted Shel knew much better.

At first surprising, I found this anxiety over the moral effect of his verses to be endearing. It foreshadowed days like the one months later in New York when Shel phoned to request an emergency seance at his publishers. He was editing his next children's book, The Light in the Attic, and Harper & Row had assembled a pint-sized focus group in a conference room to test market the verses. Shel had been reading to the kiddies, he said, and they didn't seem to be getting anything. Would I come up and give him my opinion?

"I'm not a kid, Shel."

"You're more a kid than these fucking midgets."

Shel needn't have worried. The Light in the Attic went on to become one of the surprise best sellers of all time.

Our week of meetings and parties in LA went quickly. When Judy and I left, Shel laid his manuscripts on me, as promised. Then quietly, almost meekly, he suggested that after I had read them over I should send them to the editors in Chicago.

That was it. The mock mutiny was over. But by then I gathered that mutiny had never been the point. Shel and I were never going to be Rodgers & Hammerstein. We were Huck and Tom, smoking cigarettes behind Aunt Polly's back on an island of bad boys in the Mississippi. By treating me to the hush-hush of jive intrigue and a week at the Playboy Mansion with my girl, Shel had bought my allegiance. No longer an artist on assignment from the magazine, I was now his sidekick, his Tonto, his Robin. And he knew this purchase meant that on some level I wouldn't be working for Playboy, for the editors, for the art directors, or for Hugh Hefner. From now on, when Playboy sent Shel's rhymes to me, he knew I'd be working for him.

[Shel Silverstein died unexpectedly in Key West last year. I hadn't seen him for a while, but to remember him brings back happy times. This was written for a privately published book, produced by many of Shel's friends.]