When Hugh Hefner quit his job at Esquire to start a magazine called Playboy, he didn’t just want to make money, he wanted to make dreams come true. The first issue had a Sherlock Holmes story by Sir Arthur Conan Doyle, an article on the Dorsey brothers, and a feature on desk design for the modern office. Hefner wrote much of the copy himself and drew all the cartoons. But the most memorable part by far was the set of pictures he bought from a local calendar printer of a scantily clad Marilyn Monroe.

In this wise and penetrating biography, intellectual historian Steven Watts looks at what Hugh Hefner went on to become and how he took America with him. Hefner became one of the most hated and envied celebrities in America, standing just barely on the wrong side of decency — with as many as seven million subscribers to his magazine.