How James Kaplan Paints Music with Words


Every once in a while, a book comes along that makes you want to become a better writer. You cannot always predict when those breakthroughs will happen. A case in point: James Kaplan’s two-volume biography of Frank Sinatra, Frank:┬áThe Voice and Sinatra:┬áThe Chairman (the latter of which was published in October 2015). I read the sprawling books to immerse myself in one of the most storied lives in show business. And although Frank Sinatra’s life makes for riveting reading, with its dramatic peaks and valleys, Kaplan’s lyrical phrasing, like Sinatra’s singing, shimmers, soars, and inspires.

Sinatra’s story is well known, and Kaplan covers it all: his rise of greatness as a teen heart throb, his breathtaking fall from the top, his return from nowhere with his Oscar-winning performance in From Here to Eternity, the torch he carried for Ava Gardner, his seedy association with the Mafia and pathetic relationship with John Kennedy, and, of course, the performance and recording of some of the greatest works of singing in the 20th Century or any century for that matter.

Kaplan shares one juicy anecdote after another, such as Sinatra’s cringe-worthy temper tantrums and dustups, cocktail swigging, high rolling hijinks with fellow rat packers, and transcendent moments in concert and the studio. Other biographers have covered this ground, too. But Kaplan goes beyond telling stories to share his own insight on Sinatra, thus adding the context of meaning, as in the following:

He lived with loneliness: the solitude of the only child who grows up with inexpressible feelings of otherness, the self-inflicted isolation of the man who’d brutally pushed Lauren Bacall away, the aloneness of the great artist who mused on the sonorities of Ravel and Ralph Vaughan Williams while feeling compelled to pal around with hoodlums . . . He was a kind of hunger artist, one who starved himself so the rest of us could feel better about our own hunger.

In one passage, Kaplan expresses both Sinatra’s contradictions and appeal through the lens of loneliness, one of the defining attributes that would shape his life, and essential to understanding his art and his actions. Elsewhere, Kaplan calls upon some kind of extraordinary writing muse to drop brilliant phrases on the reader like polished word diamonds. For instance, Kaplan describes the complex web of relationships in Sinatra’s life as his “strange orbit.” Ava Gardner, for whom Sinatra infamously left his wife, Nancy (triggering his career nosedive in 1950), “kept a kind of pilot light of agitation burning in his life.”

Of Judith Campbell Exner, the call girl who Sinatra introduced to John F. Kennedy, Kaplan writes, “The light of truth bends around her presence in any historical narrative, because of the gravity of her known associations — with Frank Sinatra, Sam Giancana, and John F. Kennedy.”

When Kaplan takes the measure of Sinatra’s music, he also descriptively and vividly, as when he describes Sinatra’s voice, worn down after a demanding tour in the early 1960s, as “a gorgeous ruin, deep and resonate, but hoarse and cracking periodically.” Kaplan’s triumph is capturing the essence of the songs Sinatra recorded — their color and impact — without getting tangled in technical jargon. Instead of describing sound, he paints impressions. For instance, he describes the 1961 Sinatra collaboration with arranger and conductor Billy May on Swing along with Me thusly:

From the rip-roaring castanet camp of “Granada” (May actually had his sidemen chant “cha-cha-cha!” at the end) to Frank’s magic-carpet-like vocal soaring over the twinkling, tinkling Arabian-bazaar melodrama of “Moonlight on the Ganges” to the thrill of the closer, “You’re Nobody ’til Somebody Loves You,” which starts as a caress and finishes as a powerhouse, a sprit of sheer fun infuses the Reprise LP, showing to what heights this artist was capable of ascending when he was artistically engaged.

He captures the legendary interplay between Sinatra and his musical collaborators with a keen ear for how words sound to the reader, as well as an eye for imagery, as in this description of the song “Lady Is a Tramp”:

Sinatra gave the tune a loving, lilting reading at a medium-swing tempo, launched by Bill Miller’s deliciously inventive piano reading (improvised and not written, and showing the great keyboardist, as in many other instances, to be his boss’s musical equal). Then, opening like a great jewel box, comes Riddle’s terrific chart, with its sequential reveals of strings, woodwinds, and brass (including Harry “Sweets” Edison’s dulcet, minimal trumpet fills).

Another writer might have provided a more technical description, as author Jonathan Gould often does in his book about the Beatles, Can’t Buy Me Love. For instance, in discussing the Beatles song “Happiness Is a Warm Gun,” Gould writes, “In the second section, where the harmony equivocates between A major and A minor and the meter equivocates between 9/8 and 12/8 time, John [Lennon] seems to inhabit this predatory character.” There is nothing wrong with Gould’s style; he’s simply assuming a certain amount of musical knowledge on the reader’s part. Although it’s clear that Kaplan is steeped in the arcane language of music, he chooses a more impressionistic style with phrases such as “opening like a great jewel box.”

When he writes about music, James Kaplan crosses the line from impressing me to inspiring me. I often write about music, but I typically write about the music industry as opposed to music itself. Describing music can be intimidating. The writer must find a way to convey for the reader’s eyes an abstraction meant for the ears. Kaplan has challenged me to push myself to get better at this most demanding act of writing. A recent blog post I wrote about The Revenant music score is the result, and I am going to find more opportunities to write about music. Thank you, James Kaplan.

What books have inspired you to be a better writer?