Shel Silverstein, commonly known as a children’s author, and arguably most famous for The Giving Tree, got one of his first big breaks as a cartoonist for Playboy Magazine between 1957 and 1968. He was given the enviable task of traveling the world and sending dispatches back in the form of autobiographical sketches and cartoons. These pieces have been collected in a well-designed coffee table book, and while they are far from Silverstein’s best work, they’ve held up pretty well, amusing both as an artifact of the era, and because of Silverstein’s dry, self-deprecating wit.

Prior to the travel gigs, Silverstein was already a bit of a renaissance man—playwright, songwriter, lyricist—plus a regular cartoonist for Playboy Magazine and a good friend of Hugh Hefner’s. When he decided to pay an extensive visit to Japan, it was Hefner’s idea to have him send back travel cartoons, and also, for Silverstein to include himself in the pieces, a concept originally unseemly to Silverstein. However, with Playboy paying the travel expenses, he agreed, and over 11 years, filed 23 dispatches from far-flung places, among them Scandinavia, Spain, Mexico, Moscow, and Africa.

Each dispatch contained about a half dozen dashed-off drawings by Silverstein, a few photographs to prove he was actually where he said he was, and plenty of humor, not all of it, but most of it, detailing the difficulties of getting laid in foreign cultures. A typical gag, this one from the dispatch from Scandinavia, has Silverstein talking to an overly bundled local of indeterminate gender, and saying, “If you’re a girl, how about having dinner with me tonight?”

The travel pieces are amusing, but never really laugh-out-loud funny, and the whole enterprise comes off, somehow, as quaint, a word probably not often associated with Playboy. Still, the word fits; Silverstein, in the self-portraiture of his cartoons, comes across as a little nebbish, an innocent in the world of jet-travel and free-love. He’s living the promise of the Playboy lifestyle yet he’s never 100 percent sure of himself, and he’s definitely never taken with himself. In some ways, he’s the anti-Hefner.

The best travel pieces are the ones where Silverstein doesn’t travel far. In one, he reports back from Greenwich Village, skewering the beatnik scene of 1960, and in 1968 he travels to San Francisco to be among the hippies. Photographs show him hanging out with the street people in Haight-Ashbury, and attending a nude body-painting party. The cartoons display a blistering wit about the pretentiousness of the hippie scene—a girl Silverstein is making love to says, “I’m doing this as a statement of independence, a rebellion against my parents and a protest against outdated puritanical morality. Why are you doing it?”

He also satirizes, surprisingly, the ravages of drugs: the same girl, in another cartoon, states, “Oh, Shel, what a beautiful day! We’ll take some Dexi to get us going ... smoke some pot to make breakfast taste better ... then we’ll take that acid trip I’ve been promising you ... and tonight we’ll sniff coke to help us make love.” In the accompanying drawing Silverstein draws himself looking toward the reader, a bewildered look on his face, the look of the common man dropped down into an uncommon world.

The funniest piece is the one in which Silverstein immerses himself, disrobed, into the culture of an American nudist camp, in one cartoon asking a completely nude woman standing in front of him if he can take a peek under the Band-Aid she has affixed to her shoulder. The other piece worth mentioning is Silverstein on Fire Island from 1965, in which Silverstein mingles among the vacationing gay population, mining humor, but never stooping to ridicule those who are different from him.

Silverstein stopped the travel pieces right around the time he was becoming increasingly famous as a writer of children’s stories—The Giving Tree was published in 1964—and, in particular, a master of children’s verse. The work that’s collected in Silverstein’s two most famous books of verse—Where the Sidewalk Ends and The Light in the Attic—are the types of drawings and poems that make you want to read them again, or read them aloud to someone. The travel pieces, on the other hand, while amusing, feel dashed-off and fairly dated; the hardcover book is ultimately only for the Silverstein completist, or maybe it would make a decent Christmas present for your recently divorced uncle who’s started wearing smoking jackets.

Silverstein died in 1999, and considering his prolific output, a lot was lost when he had a heart-attack before reaching 70 years of age. His death haunts the mini-travelogues collected in the book, although, to me, these pieces had a haunted quality all their own—they profile an era that now seems farther away than the years would suggest. All told, Silverstein’s travel pieces are like some of the fringe countries and cultures that he explored: not essential, but worth a visit.