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If reading, like flagpole-sitting and marathon dancing, were to qualify as an endurance event, Will Friedwald’s Sinatra! The Song Is You: A Singer’s Art could serve as the championship tie-breaker. This stupefying analysis of Frank Sinatra’s recordings plumbs new depths of self-indulgence and unreadability. The tome’s triple title and nine dedications alert potential readers to the author’s logorrhea. If something’s worth saying, Friedwald feels no compunction about repeating it three (or 30) times. Like the thin individual reputedly hiding within every fat person, an enlightening 80- or 90-page monograph lurks in the pleonastic blubber of this punishing treatise, the latest and longest in a series of offenses Friedwald has perpetrated in the name of music criticism.

I first became aware of Friedwald a decade ago when he supplied liner notes for a collection of Anita O’Day reissues. Commenting on two 1950 tracks, he observed: “The next session lists two names that cannot be accounted for: “Chuck Darwin’ as songwriter and “Paul Jordan’ as pianist-conductor. The names may be pseudonyms or they could represent no one at all.” In fact, those names should be familiar to anyone who presumes to write about jazz; Darwin’s songs were recorded by Carmen McRae, and Jordan was a gifted arranger held in high esteem by Chicago musicians in the ’40s and ’50s. Friedwald’s ostrichlike assumption that anyone he wasn’t familiar with couldn’t possibly exist marked him as someone whose writing was not to be trusted.

Subsequently, Friedwald bluffed his way into the pages of the Village Voice and other periodicals, and in 1990 published Jazz Singers, an ill-judged, error-riddled, grotesquely written survey of jazz and jazz-influenced vocalists. (One particularly vile excerpt from his commentary on Connee Boswell’s singing: “Unlike [Mildred] Bailey’s thin, delicate wisp, which, though charming, represented a coy middle-American attitude toward sex, Boswell’s is a more directly sensual, genuinely vaginal instrument, something else she picked up in New Orleans. That isn’t fur on her voice, honeychile, that’s pubic hair.”) Inexplicably, this misbegotten opus was praised by, among others, Mel Torme and Tony Bennett, and somehow established Friedwald as an authoritative critic-historian. Like the old Borscht Belt gag about the priceless Goldstein diamond that comes with a curse—Goldstein—at least half of the long-out-of-print jazz vocal recordings currently being resurrected on compact disc arrive outfitted with his liner notes. Here’s a typically ungrammatical extract from a recent Peggy Lee-George Shearing reissue: “Beauty and the Beat is like when a beautiful but formal woman, normally the height of elegance, invites you over for a drink and, to your surprise and delight, offers to slip into something a little more comfortable; the polished pussycat turns into a sensual tiger.”

Sinatra!, Friedwald’s magnum opus, isn’t as deliriously crummy as Jazz Singers, but it’s even more irksome due to its cumbersome structure. Those who survive the preface—a 40-page overview of the “Sinatra Style,” including 10 pages comparing the singer’s 33 recorded versions of “Night and Day”—are rewarded with individual chapters examining Sinatra’s collaborations with bandleaders Harry James and Tommy Dorsey, and arrangers Axel Stordahl, Nelson Riddle, Billy May, and Gordon Jenkins. Because the singer’s long associations with these arrangers overlap—Riddle and May (1953-79), Jenkins (1956-81)—Friedwald keeps tacking back and forth through time, retracing his steps like a swimmer combing a beach for lost car keys. Sinatra! reads less like an assessment of a vocalist’s art than a case study of an author’s obsessive-compulsive behavior.

To be fair, Friedwald offers some illuminating insights into the evolution of Sinatra’s recordings for readers with enough pertinacity to pan the valuable nuggets from the mounds of sludge. An indefatigable researcher, Friedwald interviewed dozens of Sinatra associates for this project—musicians, arrangers, singers, composers, and producers. But he lacks the discrimination to concentrate the fruits of his research, cramming the book with redundant quotations along with details of mind-boggling irrelevance. (In a footnote, he lists the names and birth years of Riddle’s seven children, including a daughter who only survived six months.) One can’t help recalling poet Donald Hall’s anecdote about the deceased miser, among whose possessions was found an enormous box labeled “Strings Too Short to Save.”

What’s valuable about Sinatra! is fatally compromised by its blunders and excesses. Friedwald can’t resist making grandiose assertions to elevate the stature of his subject. Sinatra, we’re told on page 11, is “our culture’s greatest popular artist.” (Not Billie Holiday, Fred Astaire, Buster Keaton, or Duke Ellington?) “No popular recording artist,” Friedwald writes a few pages later, “has ever been as totally believable so much of the time as Sinatra.” To further inflate his tome, the author ladles on the culture sauce by inserting hilariously ostentatious epigrams by Keats, Tintoretto, C.S. Lewis, Gertrude Stein, George Sand, and, I’m not kidding, Che Guevara.

Sinatra!‘s deficiencies come in assorted shapes and sizes, not the least of which are factual errors. James M. “Caine” is not how the noir novelist spelled his name; vocalist Marlene Ver Planck is not “a singer-pianist”; the performer who had a hit with “Sunny” is not Bobby “Neff,” but Bobby Hebb. Although Friedwald claims that Sinatra’s recording of Jobim’s “Sabia” was never released in the U.S., the track appeared two decades ago on a Warner/Reprise sampler. His observation that the song’s “gnomic” lyric “intrigues without ever quite explaining what’s going on” is also misinformed: “Sabia” was composed during Brazil’s military dictatorship as a meditation on the pain of exile, symbolized by the call of the titular native bird. Even the book’s dust-jacket design, a facsimile of a 78-rpm Sinatra record in a brown paper sleeve, mirrors the mess inside. The sleeve opening is positioned at the bottom of the cover, so that when the book is held upright, one has the uneasy feeling that the fragile platter is about to slip from its sheath and shatter to bits. Whoops.

One could easily devote a 560-page volume to dissecting Friedwald’s prose style, which tends to trip on its own microscopic distinctions (“Where Swing Easy can be described as a vocal album that swings, [Songs For Swinging] Lovers is a swinging vocal album, and the difference is crucial.”) and overelaborate metaphors. (Regarding Sinatra’s recording of “Ebb Tide”: “He seems to be fighting the ocean, resisting its undertow by rowing in the opposite direction, until at the conclusion of the text when the protagonist and the world, represented by the elemental force of the water, are at last at peace.”) Unsurprisingly, Friedwald’s tin-eared writing extends to his grasp of musical terminology, which is tenuous at best. Describing “The Music Stopped” as “a tour de force of pauses and fermatas” is a tour de force of redundancy—“fermata” means “pause”—and Friedwald’s allusion to the “rubato rhythms” of another recording is oxymoronic.

In the movie Stage Door, acerbic Katharine Hepburn, upon first encountering flippant Ginger Rogers, comments, “Evidently, you’re a very amusing person.” I have a similar reaction to Friedwald’s attempts at levity; he must be kidding, but somehow I fail to get the joke. The mirthfulness of his repeated use of cartoonish archaic slang—“a swell song,” “and there’s the rub, bub”—eludes me, as do his attempts at aphoristic wit, like characterizing “Autumn Leaves” as “a French chanson about dead plants.” Some passages expire on the page. “One particularly feels disappointed at “We’ll Gather Lilacs,’ ” Friedwald writes. “At face value, Sinatra would hardly seem the lilac-gathering type, but for most of the track the singer is expert enough to convince us that he actually does give a hang about those bloomin’ blossoms.” And this biographical rib-tickler: “Francis Albert Sinatra first opened his peepers on the planet on December 12, 1915, in Hoboken, New Jersey.” Then there’s the matter of consistency. How can a writer who describes the Basie band as “an aggregation that’s at once as tight as the clothes on a floozy and as loose as the lady herself” indignantly condemn, only nine pages later, the “blatant sexism” of the song “Wives and Lovers”? That isn’t confusion on his pen, honeychile, that’s hypocrisy.

Why continue? If I haven’t yet convinced you of Sinatra!‘s monumental shoddiness, by all means rush out and buy a copy. But don’t blame me if you end up echoing the sentiment of screenwriter Samson Raphaelson who, when asked to provide a blurb for a turgid academic study about his longtime collaborator Ernst Lubitsch, responded that he found the book to be “sheer reading.”