Sinatra! The Song is You: A Singer’s Art

By Will Friedwald

(Distican, 557 pages, $40)

Frank Sinatra is not supposed to be a nice guy. Books including Earl Wilson’s Sinatra (1976) and Kitty Kelley’s His Way (1986) have made allegations about his infidelities, his emotional brutality, his short temper, his assaults on members of the press, his Mafia connections and other shortcomings. Given the outrageous debauchery of many rock stars, Sinatra’s crimes against propriety seem almost quaint. And none of them can be heard in his work. Listening to “One For My Baby,” “Angel Eyes” of “If You Are But A Dream,” fans hear a performer who can personify the emotional core of a three-minute pop song and put it across with a beautifully deceptive ease and a light, sensitive touch. And it is that ability — its development, maturation, refinement and eventual dissipation — that Will Friedwald traces in Sinatra! The Song Is You. He shows how the singer, who turns 80 on Dec. 12, learned from his musical collaborators, refined his work, became more subtle and intelligent in his interpretations, then sadly seemed to forget everything he ever know about how to sing a song or which songs were worth singing.

‍     Friedwald starts out by focusing on Hoboken, N.J.-born Sinatra’s work with small bands in and around his home town, following his musical apprenticeship for the big bands of Harry James and Tommy Dorsey. The lessons learned on those bandstands in the late 1930s and early 1940s produced the Sinatra who went on to induce swooning and frantic adulation among the bobby-soxers of the late 1940s. His complete command of the standard pop-song repertoire allowed him to convincingly portray a romantic vulnerability that teenage girls found irresistible. But as the author makes clear, Sinatra was at the same time winning the admiration of other singers and musicians by illuminating the emotion and magnifying the musicality of whatever material was in his songbook at the time. After his career stalled at the dawn of the 1950s, he came back to achieve his artistic peak. When Capitol signed Sinatra, by then 37, in March of 1953, everything clicked; Sinatra had something to prove.

‍     He really worked on those Capitol recordings, while making it seem as though singing the songs was effortless. His sensitive performances were given lovely, sympathetic settings by Billy May, Gordon Jenkins and Nelson Riddle, all of whom shared Sinatra’s sensibilities and devised arrangements that suited both the singer and the songs (unimpeachable Tin Pan Alley standards and Broadway gems). Every recording is framed by maturity and sophisticated restraint. The result was a string of seven sterling albums, which included classic renditions of such songs as “Let’s Get Away From It All,” “Takin’ A Chance On Love” and “Stars Fell On Alabama.”

‍     But less than 10 years after signing with Capitol, Sinatra launched his own label, Reprise. Friedwald suggests that the demands of running the label and a certain complacency interfered with the singer’s craft. Sinatra began recording ill-considered novelties and labored attempts to be “hep.” Listening to some of these admittedly chart-topping songs from the singer’s Rat Pack era — “High Hopes” (1959) and “Somethin’ Stupid” (1967) — is, for Sinatra classicists, like watching a usually dignified uncle dance drunkenly at a wedding. That slide bottomed out with the two recent Duets collections, both of which feature Sinatra trudging through the motions alongside the phoned-in posturing of such spectacularly unsuitable partners at U2’s Bono and Willie Nelson.

‍     Throughout Sinatra! The Song Is You, Friedwald’s scholarship is exhaustive, detailed and impressive. Sinatra turned down the author’s interview requests, but Friedwald compensates with musically germane excerpts from interviews that the Chairman of the Board granted to author Sidney Zion, broadcaster Larry King and others. Friedwald bolstered his research by interrogating dozens of players who worked with Sinatra in the recording studio or on the road. He has obviously scrutinized every sound Sinatra ever made within hailing distance of a recording device.

‍     Woody Allen crystallized the difficulty of writing a book like this by observing that “writing about music is like dancing about architecture,” but Friedwald’s knowledge of music — its structure, practice and theory in both composition and performance — and his ability to explain such potentially arcane matters for a lay readership make the book enlightening and informative. His writing is clear and focused. Except for occasional too-cute punning, his style is engaging and readable.

‍     The only serious fault lies in Friedwald’s lack of objectivity when it counts most; he cannot bring himself to come right out and label any artistic choice of Sinatra’s disastrous, even when the fact is inescapable. Another shortcoming is his apparent inability to appreciate any music composed after 1955. His writing off of rock ’n’ roll, folk and soul as “kiddie-pop” suggests he has never listened to latter-day pop music with the same acuity he brings to bear on pieces written in the first half of the 20th century. Tunes such as John Lennon and Paul McCartney’s “Yesterday” may not have been right for Sinatra, but that doesn’t make them dismissible.

‍     After the scandal-mongering by Sinatra’s unauthorized biographers, Friedwald’s ardor for Ol’ Blue Eyes is at worst understandable, and at best capable of being discounted as the zealotry of a true fan. And who better to offer such a thorough appreciation of the only aspect of Frank Sinatra’s life that really matters?