In November of 1965, the journalistic fates brought Gay Talese and Frank Sinatra together in Beverly Hills and Las Vegas, Manhattan and Hollywood. Well, sort of. They were two guys from New Jersey, both of them Italian-American, given to Continental tailoring, unstoppable ambition, and unrelenting perfectionism in their chosen crafts. Talese, the writer, was traveling on assignment for Esquire, the It Magazine of the decade. Edited by Harold Hayes, Esquire made the so-called New Journalism famous—or infamous, depending on your point of view. (Talese disliked the term, promulgated by his friend Tom Wolfe.) Sinatra, the singer, was the 20th century’s reigning entertainment icon, the Rat Pack ringleader, a tuxedoed man’s man in the shaggy era of the Beatles and the Byrds.

Just One Hitch

Hayes had commissioned Talese to write a cover profile of the singer. It was meant to be a celebration of all things Sinatra as the living legend approached the golden, if worrisome, age of 50. (His birthday was December 12.) Amid an outpouring of projects that would make younger pop stars blush (two network-television specials, two albums, a movie), the Esquire cover would top it all off. There was just one hitch: Sinatra had a cold.