IN HIS MEMOIR Music Is My Mistress, Duke Ellington devotes a section to Sinatra, kicking it off with the observation that he is “a unique individual—a primo nonconformist assoluto.” This is about as high a compliment as Ellington can pay. He speaks admiringly about Frank “as an artist” and about his commitment to race tolerance and his refusal to be bossed or tossed around. “He felt that a syndicated columnist had spoken out of turn. So what did Francis do? He slugged the cat, and then went on and upwards to still greater heights.”
Sinatra seldom recorded songs by Duke Ellington, but when he did the results were breathtaking. In “Mood Indigo” (from the album In the Wee Small Hours), there is that grand moment when Sinatra delivers the word “no” eleven times, in the verse beginning “You ain’t ever been blue.” This is a saloon song par excellence: lonesome, intimate, yet not beyond the power of music to enchant: a wail modified by a sweet melody. Frank’s other great Ellington cover is “I Got It Bad (and That Ain’t Good),” on A Swinging Affair. The song is historically associated with the female voice and a specifically female predicament, which can be summarized in ten words: “I love the bastard even though he’s a bastard.”
Sinatra sang other songs that were generally associated with female performers: “Bye Bye Baby” from Gentlemen Prefer Blondes; “The Girl That Got Away,” which had been “The Man That Got Away” when Judy Garland sang it in A Star Is Born but got a new, male-specific conclusion from Ira Gershwin at Frank’s request; “I Could Have Danced All Night,” Julie Andrews’s showstopper in My Fair Lady.
His take on “I Got It Bad” suggests not only that the song is not as gender-specific as we had first thought, but also that the singer’s expression of his masculinity includes a frank acknowledgment of a feminine side, a side that is vulnerable, gets wounded, hurts, cries, has his heart broken by a lover. It is a pity that there aren’t more Ellington and Billy Strayhorn numbers in the Sinatra playbook. Ellington biographer Terry Teachout tells us that Sinatra tried to record “Lush Life,” but that the song’s intricate melody “defeated” him.
Between Sinatra and the Duke the respect was mutual. When Ellington unveiled his forty-five-minute jazz symphony Black, Brown and Beige at Carnegie Hall in 1943, it meant a lot to him that Sinatra came backstage armed with a bouquet of roses. And Ellington is one of the hundred notable jazz musicians who, according to Gene Lees, listed Sinatra as their favorite singer. The relationship as it unfolded between Ellington and Sinatra conformed to a familiar pattern: Sinatra, when he recognized musical genius, would seek to collaborate with the person or persons involved, would figure out ways to do so, and would respond with great generosity if and when misfortune struck the other. Sometimes the product was great: the albums he recorded with the Count Basie band swing in a way that transcends the time period. You can listen today to their “Fly Me to the Moon” or “The Best Is Yet to Come” and feel the immediacy of these songs in Quincy Jones’s uptempo arrangements with lots of exclamatory brass. Sometimes the result was less memorable: the record Duke made with Sinatra in 1967, Francis A. and Edward K., was, in Terry Teachout’s words, “mostly lackluster,” and Ellington makes no mention of it in the Sinatra chapter of his memoir, Music Is My Mistress.
In 1962, Ellington signed with Reprise, Sinatra’s newly formed record company, saying he “thought it would be a very good idea to be contracted to some company which is controlled by an artist rather than a businessman. It gives the soul a better opportunity.” When Ellington was ailing, Sinatra sent his private jet to Houston to fetch Dr. Michael DeBakey, then the most celebrated medical man in the nation, and bring him to New York to examine the Duke. When DeBakey said the situation was hopeless, Sinatra sent a steady supply of flowers and fruit to the Duke’s hospital room at the Harkness Pavilion of Columbia Presbyterian Medical Center.