Sinatra! The Song is You by Will Friedwald

This Mother’s Day, I locked myself in the bathroom and finished reading Will Friedwald’s authoritative Sinatra! The Song Is You: A Singer’s Art. The book provides a comprehensive analysis of Sinatra’s dauntingly large catalogue, and an essential insight into the singer’s incredible talent and craft.

A book which can be read, if you wish.

Over the years, I’ve grown from a casual Sinatra fan into a serious one (as my wife can wearily attest). What started as enjoyment of The Voice, the style, and the general vibe has developed into a deeper appreciation of his gift of expressive interpretation and for the Great American Songbook. At least for somebody of my generation (born when Sinatra released “New York, New York”) I’m a fairly big fan.

Having said that, his catalogue (300-some CDs in print) is so large that it was sometimes difficult to know where to find quality material. I had learned long ago that some of his bigger hits of the modern era (i.e.“Strangers in the Night”, “Summer Wind”) were also songs that quickly wore thin for me. I was looking for a book that could help me find the best material away from the various single-disk retrospectives on the market. Friedwald’s book is a marvelous stroll through his career, plotting the many high points and occasional missteps (see: most stuff he recorded from 1968 on). His ear for the nuances of Sinatra’s vocal performances is especially illuminating – this is a great book to have on hand when listening to his albums, as he points out many subtleties that add depth and resonance to the experience.

There were some complaints. In the interests of painting a broad picture, Friedwald occasionally gets lost on detours when describing the professional backgrounds of various musicians who played a big role in the backing bands. While an explanation about what made that particular trombonist or drummer essential to Sinatra is welcomed, multiple pages devoted to tracing the other bands he played in usually is not. There were also about 100 tedious pages devoted to Sinatra’s 1940s output that, given the low fidelity and the overly-saccharine performances, don’t do much for me. Finally, Friedwald betrays himself as an insufferable jazz snob pretty regularly. He drops sideways digs at the Beatles, Bob Dylan, Paul Simon, Neil Diamond, Bono, and other talented, respected artists from the rock world, alluding to their poor singing and the paper-thin nature of their material. To me, this came across as smug and obnoxious (though, in his defense, Bono’s performance on his 1994 duet with Sinatra on “I’ve Got You Under My Skin” was eye-rollingly obnoxious itself).

Here are a few bits from the book I’ll take with me.

-Friedwald mades a pretty good argument that “My Way” represents a masterful performance of a really lousy song. He critiques the banal melody and the brusque, monosyllabic lyrics, but notes that Sinatra is such an expressive interpreter that he singlehandedly lifts the material into something operatic. Friedwald writes, “It’s conceivable that one could be critical of ‘My Way’ from a distance…however, it’s impossible not to be overwhelmed by it in person: how can you not stand up and cheer at the sight of a man who can, at will, grow to be ten stories tall?” (p. 447)

-Ever the man of fashion, Sinatra recorded much of his peak 1950s material in his trademark hat and trademark t-shirt with an airbrushed wolf on it.

-Friedwald does a nice job of characterizing the notable arrangers that Sinatra returned to over the years. The job of the arranger was to take an existing song and write an orchestration to it to support the singer. Thus, they fashioned the sound and the feel of a recording in much the way a modern producer does. The celebrated genius Nelson Riddle comes across as brittle and difficult, the swinging Billy May seems upbeat and easygoing, the strings-loving Gordon Jenkins as patient and sanguine. Friedwald also resurrects the reputation the sometimes-scorned Don Costa (who worked with Sinatra on a lot of his weaker late albums) as a man caught doing admirable work on projects that were woefully misbegotten (“Let’s make Sinatra relevant to the flower people!”). The details on the working relationships between Sinatra and these talented arrangers adds a lot of depth to the listening experience.

-In an attempt to maintain sales, Sinatra lost his way by the late 1960s by turning toward soft rock and away from his usual palette of standards and swing. This resulted in the embarrassing spectacle of him scatting amidst the cheeseball nonsense of “Sweet Caroline”. If Sinatra were alive today, we would all have to put up with him doing Sister Hazel’s “All For You” and pretending we didn’t hear it.

–When Sinatra recorded, he liked to set the ambiance by burning incense and lighting a single candle. He also would relax by loudly indulging himself face-first in a smorgasbord of booze and women while listening to Enya.

-Sinatra’s longtime pianist Bill Miller comes across in the text as a sort of zen saint. Friedwald celebrates the way Miller is able to effortlessly support the emotional tone of the songs while giving Sinatra both the structure and nuance he needed to shine. Listen to any live recording of “One for My Baby (and One More for the Road)” and this becomes immediately evident. Miller’s quiet, graceful demeanor also comes across as a counterpoint to many of the highly-strung musicians, and to Sinatra himself, who while capable of being generous and gracious, could also hold an ugly grudge with the best of them.

-In concert, if Sinatra ever forgot the words to a song, he later would have the songwriter beaten to a bloody pulp by his goons.

-Above everything else, what made Sinatra such a tremendous artist was his ability to make the audience feel the song. Be it exuberant or sardonic, boastful or broken, Sinatra could embody a lyric and express it like no other singer I’ve ever heard. I was watching some clips on YouTube of vintage live performances and I was struck by how much he seemed to be processing and thinking about every word he sang. There were only rarely moments of rote singing. He famously once said, “When I sing, I believe.” Ultimately, that’s what makes his music worth returning to.

-I bet when Sinatra sang love songs, he thought about me.

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2 Responses to Sinatra! The Song is You by Will Friedwald

  1. _steve says:

    I frequently sing, hum, or imagine Sinatra’s rendition of The Girl from Ipanema. Even after so many years of doing so, the song still gives me chills.

  2. Peter says:

    I love that tune. What an amazing vibe.

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