‘The Song Is You’ Is the Frank Sinatra Biography That’s Not a Biography

Frank Sinatra was, in many ways, the consummate entertainer. He seemed genetically engineered to be a celebrity. Possessing an impeccable voice, magnetic good looks, and irrepressible charm, he was also an acclaimed film actor whose affiliations with politicians on both the left and (later) the right incited both approval and ire. There were also multiple marriages and, lest we forget, alleged ties to organized crime. It’s no wonder HBO’s two-part, four-hour Sinatra documentary Sinatra: All or Nothing at All (2015) only seemed to scratch the surface of his biography.

But what jazz writer and historian Will Friedwald originally published in 1995 offered a refreshing take on the Sinatra legend – a book about Sinatra the vocalist, concentrating on the music and nothing but the music. There are no salacious tales of love affairs or failed marriages, no true crime-style anecdotes of backroom cosa nostra lore, no accounts of film studio wheeling and dealing. Sinatra! The Song is You: A Singer’s Art was at the time – in addition to being a rather lengthy and laboriously titled book – the definitive guide to Sinatra the singer. Countless collaborators, musicians, arrangers and Sinatra himself were interviewed for the book, offering insight to the Sinatra sound and who and what was involved in its success.

Nearly a quarter-century has passed since the book was published, and – most notably, Sinatra himself died in 1998. While Sinatra was essentially inactive during the three years between the initial publication of this book and his death, Friedwald saw fit to update and revise the book for a 2018 version(Chicago Review Press). As a result, more than 100 pages of new information has been added, including a comprehensive discography, a slew of rare photos – which, true to form, focus on recording sessions and live performances, as opposed to glitzy film premieres and awards shows – and both a new introduction from Friedwald and a new foreword from Tony Bennett. The latter is written in Bennett’s typically reverent and self-deprecating style, reminding the reader of Sinatra’s gifts. “He perfected the art of intimacy,” Bennett writes, “And that was a big contribution to the art of popular music.”

As is expected in a book of this nature, sections are divided along the lines of bandleaders and arrangers who helped shape Sinatra’s sound: “Hoboken and Harry, 1915-1939” details his beginnings and eventual collaboration with Harry James; subsequent chapters pair him with the likes of Tommy Dorsey, Axel Stordahl, Nelson Riddle, Billy May and Gordon Jenkins, towering musical figures whose collaborations with Sinatra helped define 20th century popular music. Concentrating on “a singer’s art” seems like a natural and unjustly overlooked slant on the Sinatra legend, and while he seemed comfortable schmoozing with Hollywood, the studio and stage was where he seemed most at ease. Friedwald understands this only too well, recounting a story from 1957 where Sinatra threw a lavish bash that was a veritable who’s who of Hollywood elite. “Still, the biggest celeb of all,” Friedwald writes, “The blue-eyed one himself, spent the entire evening ignoring the Hollywood crowd in order to split a pizza with a handful of studio musicians and their wives, whom he’d also invited.” It’s a wonderful image. To put it in blunt, present-day terms: It’s about the music, stupid.

Friedwald’s love of Sinatra’s music is certainly no secret to anyone who read the original version of the book, and at times his appreciation borders on fawning. But how else do you write about an artist whose art involves a wealth of superlatives? Building on the crooning style of his idol, Bing Crosby, Sinatra helped establish a more nuanced vocal style, and one that inspired countless singers to this day. His ability to juggle a variety of styles with little to no stumbling is also noteworthy. You could also make a case for Sinatra as the original “album” artist, crafting what became known as the “concept album” years before it became commonplace with albums like In the Wee Small Hours, No One Cares, Watertown, Cycles and the ambitious Trilogy project. Friedwald picks apart these projects and also offers plenty of music theory that might intimidate the casual fan. But make no mistake: this is a deep-dish exploration with no attempt to disguise it as anything else.

When Sinatra passed in 1998, Friedwald notes that “he left the world a very different place than the one he had entered in 1915. He had completely changed the way we listen to music, in particular the role of singers and the songs they sing, and with it the relationship of both songs and singers to the audience.” With The Song Is You, Friedwald cuts out the extraneous noise of celebrity and boils the legend of Sinatra down to its very essence: a singer of songs.