For much of the 1960s, a relatively unknown Shel Silverstein was Playboy’s “roving Renaissance man” and later became yet another of our gifts to the world of pop culture. He won a Grammy for writing the Johnny Cash song “A Boy Named Sue” and sold more than 35 million copies of his children’s books (Where the Sidewalk Ends and A Light in the Attic, among others). He has remained one of our favorites, and we thought this was the perfect time to revisit some of his more memorable exploits.


“I…I really can’t find the words to express it. Here I am in Taxco, the most enchanting city in the world…a beautiful girl at my side…an orange sun burning in the clear azure sky…the rows of picturesque adobe houses set along a lazy street…a gentle breeze caressing our hot bodies…the romantic sounds of a guitar being played in the distance…and I think I’m getting diarrhea.…”

“You Americans are never satisfied! I get us two good seats for the corrida and you complain because we’re in the sun…so we exchange them for seats in the shade and you complain that we’re not close enough to the bulls…so we get the closest seats possible, but now you still complain!!”


“You see, you pack the snow into balls like this, then you choose up sides and.…”


“…And so the good kind lion let the little mousey go free and later when the lion was trapped in a big net and couldn’t get loose, the grateful mousey came to his aid and gnawed through the net and saved his life and.…”

“What do you mean you just remembered you can’t stand the sight of blood?!”


“You’ll like Urla…she’s a typical Scandinavian girl…blonde hair…blue eyes…nice figure…tall.…”


“I don’t know the exact address, but it’s right behind a church.…”


“Aloha, sir…and I hope you enjoy Hawaii, sir…and it’s spelled l-e-i, sir…and I’ve heard that joke 3,227 times, sir.…”

“You see, Mr. Silverstein—in the hula, the story is told with the hands…the hands, Mr. Silverstein…you have to watch the hands. The story is…uh, Mr. Silverstein…Mr. Silverstein.…”


In an inn of legendary Granada, Shel dances the traditional flamenco with a group of high-spirited gypsies. Wherever he roams, he trips the local fantastic, sings local songs.

“Okay, but now let’s look at it from the bullfighter’s point of view!…”


“I believe I can say with assurance, sir, that Princess Margaret will not be interested in appearing as January’s Playmate of the Month.…”

“Well, they don’t call them sentry boxes where I come from…! But it was an honest mistake…and I said I was sorry…and I will clean it up!”