Shel Silverstein On Trying to Make it in New York City

I cannot even begin to describe what a goldmine of information Paul Krassner’s “impolite interview” with Shel Silverstein in the August 1961 issue of THE REALIST is. References to a TV appearance on the Roger Price show (dressed up as an executioner, no less!) Riffing on Lenny Bruce! Talking about covering political conventions for the Chicago Sun-Times! And on and on. But what I wanted to pull out, in large part because it is funny but also because things haven’t really changed all that much, is Shel’s description of his very first trip to New York City at the tender age of nineteen* and the cringe-inducing hilarity that would ensue:

I was nineteen years old, and I was at the Academy of Fine Arts in Chicago, and I was a real hot-shot cartoonist, doing about fifty gags a day. So I decided I was going to New York and try to break the markets. I had a couple of hundred cartoons. I'd been mailing stuff and hadn't sold anything in about a year, so I figured I'd do it in person.

I got on a Greyhound bus – fortunately, I got a two-way ticket – and I'll never forget, it was a real thing. There were these sailors that were on the bus, and they had a couple of bottles and got really blasted. There's nothing grimmer or grimier than a long Greyhound bus ride, where everything gets sort of greyish-brown after a while, and you keep stopping in these places for rest that you don't really need, and they have these grim wooden places where they have sandwiches wrapped in cellophane, and everything's dry, so you get a drink of water and you hang around.

Finally, we got to New York. I had gotten all the information from somebody who'd already been here — the best place to stay, and where to eat — he told me to stay at the 34th Street YMCA, and he said there's a place right across the street where you can eat, and they serve you fried eggs right in the frying pan. So I went there, and I ate fried eggs for three days, from a frying pan. I don't know what day I arrived but it wasn't what the editors call a "seeing day." Nobody would see me at all. And they wouldn't have seen me anyway, because they only see guys who've sold stuff. 

So I finally went to Collier's, and Gurney Williams was the cartoon editor there – he's now with Look – and he was like a legend among young cartoonist. I really, physically pushed my way by to see him. And he said okay — I guess he was scared — and he told me to come back after he had lunch. He looked through a hundred cartoons, the greatest ones ever drawn – at nineteen, I was doing only great cartoons – and he bought none.

And so I went back to Chicago. I got in the bus, and there was a girl sitting next to me, and so I thought, well, at least I'll make out with the girl so it won't be a total loss, you kno. Some old Jewish mother had put her daughter on next to me, and she was very worried about her, so she said to me, "Are you Jewish?" Andd I said, "Yes I am." So she felt good about that, see, little dreaming of all the consolation I needed for my disappointment. I thought, well, at least something, you know?

So the bus hit out, and about half an hour outside of New York, the girl got car-sick, puekd all over my shoulder – she had gone to sleep on my shoulder, and I thought, well, this is the first step; next thing I knew she was puking on my shoulder – and I spent the whole trip ringing for the bus-driver to stop, and she kept puking and moaning, and I kept washing my shoulder off. Just a real mess.

I got to Chicago and I was a complete failure. Not only Gurney Williams, but this girl was vomiting on me. Everything was wrong. There were some pretty horrendous experiences in the YMCA, too. Because at the time I thought this was a place where all the he-men gather. Where young Christian men gather, you know. And it's not quite that. It makes Sixth Avenue and 8th Street late at night look like a cub scout meeting…

The surface trappings have obviously changed (Sixth Avenue and 8th Street is a lot closer to a cub scout meeting now than it was then) but 50 years later, it’s still mighty difficult to make it in the city – and often involves humiliating Greyhound bus rides.

*Silverstein claimed he was nineteen “ten years ago” which would have made this event happen ca. 1951. In actuality he was twenty or twenty-one, and I’m not sure exactly when or why he started shaving a year or two off his age, but I suspect it had to do with preconceived notions about how old a man must be in order to get his first regularly paying gigs. It also seems likely that this interview perpetuated the idea that he was born in 1932, and not 1930.