During the first decade and change after its debut issue in December 1953, Playboy magazine ran an occasional “On the Town” feature designed as a “cosmopolitan’s guide” to national and international cities — Paris, Tokyo, New York, London and others — that were becoming accessible to the publication’s upwardly mobile male subscribers, thanks to the rapidly expanding network of airline travel. The June 1958 issue was highlighted by a lengthy focus on San Francisco: where (and how) to lodge, dine, drink and be entertained.
Since Hugh Hefner was an avid fan of mainstream and progressive jazz, the exhaustive article included a generous coverage of Baghdad-by-the-Bay’s then boisterous nighttime jazz scene. (The action probably was richer and more extensive right then, than at any other point in time; many of the clubs cited would close, change hands or go bankrupt within the next few years.)
Although the article makes fascinating reading as a time capsule, one must, ah, tolerate the wincingly archaic “dating tips” sprinkled throughout, such as…
[San Francisco] is a place of beautiful women, characterized (more than in any other city) by independence, good jobs, a friendly love of pleasure, hideaway apartments of their own, unpretentious poise, and an utterly charming knowledge of how to dress and behave, to please a man.
…and…
Your first stop, preferably just before sunset, should be the Mark Hopkins, up at the glass-enclosed Top o’ the Mark. Relax, have yourself a drink, take time to watch the sunset, and get the feel of the city here. Many a San Francisco visitor settles for the first girl he meets — only to rue it later, when finer prospects cross his path.
(Ouch!)
Further along, having offered suggestions for the best dining and dancing, we finally come to the late-evening options. I’ve extracted those with a strong — or even fleeting — connection to Guaraldi’s career, at that moment or soon to occur:
…
