image galleriescontactsubscribe

Shel Game

APRIL 16, 2010
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.  In the summer of 1978, he thought they were best in Chicago. Shel had gone there to interest Playboy in a series of ribald ballads he was writing in comic verse.  Kerig Pope, the assistant art director, called me and introduced us over the phone.

Shel had been a Playboy regular for over 20 years.  He was looking for someone to illustrate  the new series. Kerig recommended me. The first installment was a long fable called "The Devil & Billy Markham." I painted a Devil for it and did a dozen pen and ink drawings. Shel was happy. So were the editors. So was I. The reader response was great and the series was off and running.

We began working as you usually do with a magazine.  Shel sent his rhymes to Playboy. Playboy sent the rhymes to me.  I sent pictures to Playboy.  It was simple enough.  But as the series developed and Shel began to conjure up his fictional world of night owls, coke dealers, babes and good ole' boys, he decided it would be a fine idea for the two of us to streamline the collaborative process as well.

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

The idea appealed to me. Doing away with the Chiefs always appeals to you when you're one of the Indians.  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 to.  "OK, Hammerstein," I told him. "Meet Mr. Rodgers."

Shel guessed we'd work well together, but there was a catch:  He had a hard time communicating with the suits at the Playboy Building.  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 and that we were cutting them out.  

I was to say I didn't know where Shel was calling from (this was true enough). And I was to say I didn't know how to find him (this was also true).  Then I was to explain the deal:  Shel would 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 (!).

I knew this wouldn’t be welcome news to the real editors and art directors on Michigan Avenue - and Shel admitted it would be a touchy thing for me to pull off. But he said he was sure that if I handled it smoothly, the suits would only moderately freak out.  Surely they knew they could trust us.  And even better, anxiety over not knowing what they were going to get 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 with Bunnies in the magazine when I was still in high school and sneaking my father's Playboys into the barn.  Why was I now suddenly supposed to play 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 find him) and meet him (if I could track him down), then humor him and get the manuscripts away from him.  Kerig assured me that when the time came, Uncle Shelby would be a pussycat. Then I was to send the verses to headquarters in Chicago and we could all dispense with any further 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 Shel at all the numbers he had given me.  He had an apartment on Hudson Street in Manhattan, another one in Chicago, a lair in Key West, and a houseboat in Sausilito.  Houses everywhere, yet he wasn't at any of them. Finally I realized that Rodgers would have to run on Hammerstein Time.  So I waited and went about my business.  Then one morning I answered the phone and heard the familiar, good-natured croak on the other end of the line.

Where are you?" I asked.

"I'm staying at Hef's," he said, his home-away-from-homes, the Playboy Mansion in California.

"The people at Playboy are looking everywhere for you," I said.

"They'll never find me here."

Shel had been writing verse, he said.  He had lots of stuff, but he didn’t like working over the phone.  It was important that we meet soon. I should come to LA.  He'd need me to stay 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 for the coast?

"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 pinball and Donkey Kong with Hefner.  But before I could get carried away, 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 ‘Carrying Coals to Newcastle?'"  Shel took a few minutes to make sure I understood the difference between love and sex. But I was adamant that I wanted to bring Judy and Shel, no doubt scratching his shiny head, agreed to make the travel arrangements.

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 taking a sleigh to Grandma's at Thanksgiving.

It was late morning when we got to Hefnerland but the Mansion was as quiet as a funeral parlor.  Shel met us at the door dressed like an Arab in a striped floor-length robe and sandals.  The house was alive with hushed activity, just as my grandparents' house used to be in Fremont when Grandpa worked nights at the Whirlpool plant and slept mornings.

We drank orange juice in Hefner's living room as servants vacuumed  around us and emptied ashtrays from the night before.  Shel had a pile of manuscripts ready to turn over to me. They were all neatly typed, with interlineations in pencil:  "The Perfect High," "California Cs," "Rosalie's Good Eats Cafe," “Uncle Don.”  We went through them all.  They read like country western ballads in search of music.

As Judy drew crested cranes in her sketchbook and grew sunburned on the lawn of the Mansion, Shel and I  worked our way, line by line and word by word, through his inch-high pile of mansuscripts.

It surprised me to discover that his Dharma Bum demeanor masked a concern 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 powwows 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 disarming, I found this anxiety over the schoolmarmish effect of his verses to be endearing.  It foreshadowed days like the one months later in New York when Shel phoned and asked me to come to 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 market-test the verses.  

Shel had been reading to the kiddies, he said, but they weren’t being attentive. They kept crawling over and under the conference table and wouldn’t quit fooling around. "They didn't seem to be getting the point of anything," he said. He was beside himself.  Would I come up and give him my opinion?

"I'm not a kid, Shel," I said.

“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 publishing hits of all time. It was on the best seller list for years.

Our week of meetings and parties in LA went quickly.  When we left, Shel laid his manuscripts on me, as promised.  Then quietly, almost meekly, he suggested that after I had read them, maybe I should send them to the suits in Chicago after all. Maybe we should humor them, he said. Let them decide which stories to use and in which order.

And so that was that.  The mock mutiny was over.  But by then I gathered that mutiny had never really been the point.  Shel and I were never going to be Rodgers & Hammerstein.  We were going to be Tom and Huck, two bad boys sneaking away from Aunt Polly and smoking cigarettes on an island in the Mississippi. 
By treating me to a lot of hush-hush and 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 buddy. And he knew this meant that in the future, when I worked on his series, 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, Shel knew I'd be working for him.

Over a period of several years, Shel and I collaborated on probably a dozen features in all. He died unexpectedly in Key West in 1999. This was written for a privately published book, produced by many of his friends.
Except for the two diner pictures, and the drawing of kids fooling around, all the ink drawings here came from "The Devil and Billy Markham." The diner and pinball drawings, and the pencil sketch of the woman at the cash register came from "Rosalie's Good Eats Café." The pencil drawing of the devil was a working sketch for "Billy Markham." The pencil drawing of Judy drawing came from my sketchbook of our California trip.
Text and all images © Brad Holland and/or Playboy Magazine.
Any reproduction by any means, without written permission, is strictly prohited.