If America experienced a sexual revolution in the latter half of the twentieth century, then one of the first shots surely was fired by Hugh Marston Hefner in 1953, the year that he introduced Playboy magazine to the world. The first issue of the magazine featured a centerfold of a nude Marilyn Monroe (who had posed for it years earlier, before attaining the stardom she enjoyed in 1953), and it sold well enough to guarantee that other issues would follow in the months to come.

The "shocking" new magazine was based in Chicago, the city where Hefner, the older of two sons, had grown up in a typical middle-class household. After army service and college, Hefner married and then tried to earn a living as a free-lance cartoonist. In this he was unsuccessful, but he did land a low-level job with Esquire magazine, the most prestigious...