How Billie Holiday Hovers Over Bob Dylan’s Sound

Does Dylan Owe an Unacknowledged Debt to Lady Day

While listening to the jazz singer Billie Holiday’s celebrated late record Lady in Satin, from 1958, I was struck by repeated aural reverberations that wanted to connect with Bob Dylan. Here was, like Dylan, a performer with a distinctive, idiosyncratic voice making singular, artistic expressions with the lyrics of a dozen songs.

In its day, Holiday’s sound could be divisive, as Dylan’s has always been from the very beginning, six and a half decades ago, and throughout his many stylistic evolutions ever since.

As Dylan’s latest tour proceeds and approaches Kansas City once again (July 4, 2026!), the evidence of Dylan’s divisiveness may well emanate from the stage but, as I’ve heard in quite a few of his concerts in the last few years, the evidence of his perhaps secret devotion to Billie Holiday can also be detected in significant ways.

In 1958, some 25 years into her singing career and a year before her death, Holiday was struggling with drink, drugs, and a disturbingly violent marital conflict. Yet she made it through three late-night recording sessions, often haltingly, and produced these songs of heartache that to today’s ears become instantly mesmerizing: “I’m a Fool to Want You.” “Glad to Be Unhappy.” “You Don’t Know What Love Is.” Awesome.

Count Basie, who employed Holiday in his band in the late 1930s, once noted that she “had a really strange way of delivering a song.” Yet, he added, “All so wonderful.”

The glory of Holiday’s story is how she fought through physical and emotional pain to produce a lasting art. As one critic put it at the time, “Billie’s ruined voice is itself enough to make one weep, but she uses the poor fragment with tremendous style and feeling.”

Think of how many times we hear admiration for the way Bob Dylan phrases, rephrases, and experiments with the phrasing of even his own classic songs. And think of the way that Dylan, with his sandpaper-edged and tannin-tinged vocals, not long ago turned back to American standards in recordings and concerts.

Dylan’s string of standards records, including Shadows in the Night (2015), Fallen Angels (2016) and Triplicate (2017), amount to a collective tribute to Frank Sinatra, whose crooning heights and exquisite ways with a song Dylan wanted to emulate.

Yet Dylan didn’t have much to say about Sinatra in his book The Philosophy of Modern Song (2022), which finds him musing about 66 records that informed his ears, especially in his early musical life. Dylan tells us that for some reason Sinatra hated his own melancholy pop hit “Strangers in the Night,” but little more. Elsewhere in the book, Dylan mentions Billie Holiday only in passing.

I was prompted to go back to Lady in Satin while reading a recent biography, Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year, by Paul Alexander. As Alexander reports, Holiday contends she taught Sinatra how to “bend a note,” which “became the hallmark in his singing style.” There’s no reason to doubt this, which leads one to conclude that the line from American songbook to Dylan ought to extend back through his hero, Sinatra, to the previously unacknowledged Billie Holiday.

In many ways Holiday can be seen as a ghostly presence in the Dylan story, a diaphanous mystery waiting to be identified and appreciated.

Here are some small recent hints:

In the Dylan biopic, A Complete Unknown, for the briefest of nano-seconds you can see Timothée Chalamet as Dylan, on a visit to the Columbia Recording headquarters in New York, strolling by a famous poster-sized photograph of Billie Holiday. This is a reminder that Dylan was signed to the label by John Hammond (Dylan and Hammond below), who notably counted Holiday among his many recording successes.

Two: When flipping through the record bins in the shop of the Bob Dylan Center in Tulsa, Oklahoma, I was surprised to find copies of Lady in Satin. Is someone else in Dylan World thinking what I am thinking?

Thirdly, and oh so intriguingly, take a close look at the back jacket cover art of Philosophy of Modern Song (below). It’s a colorized version of a famous photograph by William Gottlieb taken in the Commodore Record Shop, in New York in 1947. There, in the lower right corner, is a salesman (not Billy Crystal’s father, who is also in the photo) holding Billie Holiday as she appears on the cover of a newly released Commodore album. This cannot be an accident. Dylan is very much telling us something important here.

One more: In 2025 Barbara Streisand released a new record of duets, The Secret of Life: Partners, Vol. 2, including Dylan among her A-list song companions. Dylan and Streisand had been long-distance admirers but had never recorded together. What song did Dylan offer for the session? Answer: “The Very Thought of You,” which Billie Holiday had turned into a hit for Columbia in the mid-1930s. (I’ll refrain from judging the resulting duet.)

The Dylan archives in Tulsa hold no clues that I could discern of a hidden passion he might have felt toward Holiday. When Dylan wrote “postcards of the hanging” at the beginning of “Desolation Row,” for example, we can only imagine him thinking about or reflecting on “Strange Fruit,” the chilling song about the epidemic of lynching of Black Americans that Holiday began making famous not long before Dylan’s birth in 1941.

By the time Dylan reaches New York and begins to make musical traction in 1961, he certainly has become aware of Billie Holiday. He mentions her at least three times in the opening pages of his quasi-memoir Chronicles, Volume 1. In one instance he recalls discovering the singer Karen Dalton, who possessed “a voice like Billie Holiday.” And he cites “Strange Fruit” as among the rarely successful examples of “protest” songs, though he offers no connection to that line in “Desolation Row.”

Of the dozen tracks on Holiday’s Lady in Satin only two appear among the 52 songs on Dylan’s three collections of standards.

It’s possibly coincidental but certainly resonant to notice that the first track of Dylan’s Shadows in the Night is “I’m a Fool to Want You,” which also opens Lady in Satin. Did Dylan know this?

Frank Sinatra shared the writing credits for “I’m a Fool to Want You.” He first released it in 1951 and included it on the album Where Are You? in 1957, the year before Holiday’s version.

By singing with Ray Ellis’s 35-piece orchestra and a bevy of background singers, Holiday wanted to experience how similar strings had served Sinatra. She was well aware that the accompaniment would help cushion her fragile voice. “She wanted to be flattered by that kind of sound,” Columbia producer Irving Townsend once said. Biographer John Szwed writes that Holiday “counted on the strength of her recitative, the ability to sing out of tempo and not seem lost. Her phrasing was still sensitive to the words, remaking their points of emphasis and shifting meaning by surprising changes of stress as she sang.” Szwed, one hastens to note, could have written the very same thing about Dylan.

As for Shadows in the Night, Dylan’s overt intention may well have been to absorb Sinatra’s spirit in body and soul. But listen to Dylan’s version of “I’m a Fool to Want You” side by side with Holiday’s and you might begin to hear an even richer reverberation.

In these samples, feel free to pause after the opening phrases.

Dylan told Bill Flanagan in a 2017 interview that he had to suppress Sinatra’s

influence in those projects. “He’ll point the way and lead you to the entrance but from there you’re on your own.”

Dylan may not have been quite on his own. He very well could have had Billie Holiday on his shoulder as one of the better, if not fallen, angels.

Sinatra, even he tells us, would not be Sinatra without the power Holiday brought to his early style and career. “With few exceptions,” he told Ebony magazine in the late 1950s, “every major pop singer in the U.S. during her generation has been touched in some way by her genius.”

One could spend hours dissecting the syllables where both Dylan and Holiday waver and spring lightly from a bent note to the height of feeling, to the tracings of “romantic smoke signals” as the perceptive critic Stanley Crouch once wrote of a Holiday performance.

Dylan sings his heart out on “Triplicate,” a three-record package coursing through torch songs and classic lyrics about desire, unrequited love, and loss. At least seven of its 30 tracks are songs that Holiday was known for—“But Beautiful” (from Lady in Satin), “Stormy Weather,” “These Foolish Things,” “You Go to My Head.”

Perhaps it’s superfluous by now to think about how both Dylan and Billie Holiday go to our collective heads. But perhaps it’s not crazy foolish to think about how Billie Holiday got into Bob Dylan’s head, spun around in his brain, and about how long she has lived there so undetected.

Steve Paul presented a longer version of this article at the University of Tulsa’s World of Bob Dylan Symposium in 2025.