Let’s Be Frank

Setting aside what I have edited myself, the magazine piece I have read the greatest number of times is, without question, Gay Talese’s “Frank Sinatra Has a Cold,” from the April 1966 issue of Esquire. The 15,000-word profile was Talese’s first assignment for the iconic men’s monthly, part of a six-story trial run with its editor, Harold Hayes. Considering that Ol’ Blue Eyes had rebuffed Esquire repeatedly in the past, it was always going to be a demanding initiation. But then the subject was under the weather when the reporter from New York landed in Hollywood, and he simply refused to talk.

Much ink has been spilled about the resulting article: about how, despite the challenges Talese faced, the thirty-four-year-old managed to file one of the best celebrity profiles of all time and helped to define New Journalism itself. Still, every time I reread “Frank Sinatra Has a Cold,” I notice something I hadn’t necessarily noticed before. Beyond the...