The Legacy of Billie Holiday: Music and the work of Jose James, Annie Lennox, Cassandra Wilson, and Audra McDonald

By Daniel Garrett

Jose James is a wonderful singer!  He is suave and thoughtful, and thoughtful yet light and sensuous, when performing “Good Morning Heartache,” a song that is part of the great Billie Holiday’s legend.  Jose James has the sensuality of youth, and that gives certain songs something special—that sensuality gives him another weapon against despair, against a too predictable pathos.  His mastery of “Body and Soul” is incantatory and impressive, as it is a difficult song that maintains its difficulty despite its popularity with singers.  Such mastery is surprising for a young man.  “Fine and Mellow” is an honest and sexy song about bad love, full of desire and recognized trouble.  These three songs alone suggest how right it was for Jose James to pay tribute to Billie Holiday with his album Yesterday I Had the Blues (Blue Note Records, 2015), produced by musician and executive Don Was.  Billie Holiday has touched many singers—among them, Dee Dee Bridgewater, Diana Krall, Annie Lennox, Abbey Lincoln, Audra McDonald, Dianne Reeves, Diana Ross, Dakota Staton, Barbra Streisand, and Cassandra Wilson.

Frank Sinatra was influenced by Billie Holiday too.  It is often forgotten that men can absorb and be transformed by the power of a woman and that can be a strength.  Masculine, romantic, and elegant—beautiful and believable—is Jose James’s interpretation of the song “I Thought About You,” making it possible to see James as a descendant of both Billie Holiday and Frank Sinatra.  The musical accompaniment throughout Yesterday I Had the Blues has energy and finesse.  Jose James has excellent taste.  James, who grew up in Minneapolis and studied music at The New School in Manhattan, has liked different kinds of music—John Coltrane, Chico Hamilton, Marvin Gaye, Al Green, 10,000 Maniacs, Ice Cube, Maxwell, Frank Ocean, James Blake, Jose Gonzalez—and made several significant recordings, often experimenting with jazz, such as The Dreamer (2008), Blackmagic (2010), For All We Know (2010), No Beginning No End (2013), and While You Were Sleeping (2014), before Yesterday I Had the Blues (2015).

On Yesterday I Had the Blues is “What a Little Moonlight Can Do,” an always charming song, playfully done, with an instrumental introduction, featuring Jose James’s album collaborators pianist Jason Moran, bassist John Patitucci, and drummer Eric Herland.  Here, as well, are “Tenderly” and “Lover Man”—and the humming of Jose James near the end of “Lover Man,” a song of wonder and worry, seems an attempt at self-soothing.  “God Bless the Child” is delivered with a plain pragmatism and strong rhythm, without bitterness.  The rhythm is alluring and firm but not distracting or excessive.  “Strange Fruit” becomes a hymn—spiritual, tribal.  What a small, satisfying gem is this invocation of Billie Holiday, this claimed inheritance—Yesterday I Had the Blues.

Her small, light voice could be large in feeling, dark, devastating.  She could sound like a siren, a trumpet, a wrecked crone.  Billie Holiday (1915-1959) is one of the rare artists who seems ever more mysterious, the more time passes, the more that becomes known about her.  How did so strange a creature make such beautiful and lasting work?  Eleanor Fagan?  Elinor Harris?  Whatever name is on her birth certificate it was Billie Holiday who survived that Baltimore childhood, a child of a broken and impoverished home, then a resident in a shelter for troubled youth, a target for predators, and a prostitute (what could be more likely in a cruelly capitalist culture than to be forced to sell oneself?); it was Billie Holiday, not Eleanor or Elinor, but Billie, a singer, an innovator, an admirer of Louis Armstrong and Bessie Smith, a protégé of music producer John Hammond, a collaborator of Benny Goodman, Teddy Wilson, and Lester Young, who became a legend.  The lack of law, logic, and luck, and the love and loss, were transformed into creativity, into haunting beauty, into legacy.  Billie Holiday’s songs are testimonies and tests: here are truths; can you master them?  Bruise and balm.  Insult and insight.  “God Bless the Child” and “Strange Fruit” continue to challenge singers and listeners.  It is easier to talk about her questionable taste in men, or her drinking and drugs and the trouble that caused with the law and the newspapers, than to be precise about why her work is so strange and so strong: bitter and sweet, romantic and tragic.  How did a poor black girl come to wield such power?  It took courage to believe in her own talent and will—and to make magic with sound.  Genius.  Billie, long after her death at age 44 in Manhattan’s Metropolitan Hospital, continues to inspire—most recently, Jose James, Annie Lennox, Cassandra Wilson, and Audra McDonald.

Annie Lennox, whether with Dave Stewart as part of the Eurythmics or alone (Diva and Medusa and Bare and Songs of Mass Destruction), has proved herself one of the best and most intriguing musical artists of her generation.  Annie Lennox on her album Nostalgia grasps the songs—some of them sung by Billie Holiday—with simplicity and force (the album was produced by Lennox with Mike Stevens for Blue Note Records, 2014).  In fact, it is a little shocking to hear Annie Lennox’s emphatic embrace of such uniquely American songs as “Memphis in June” and “Georgia on My Mind.”  Annie Lennox’s interpretation of “I Put a Spell on You” has the theatricality and threat of some of Lennox’s best work—the passion and possession are easily part of her range.  Lennox opens “Summertime” with a long, delicate note.  Her voice sounds impressive in this soulfully dramatic recitation.  “Strange Fruit” remains the most disturbing of reports—precise, perverse.  “You Belong to Me,” both modern and sentimental, is, very obviously, an assertion of personal claim beyond the adventures and distractions offered by the world.  “Mood Indigo” has a jazzy rhythm the album might have used more of, with a near-improvised feel, a sense of sun, despite the theme of sadness—and it, typically, makes me wonder again what Lennox will do next.

I love and respect Cassandra Wilson, especially as she is represented by Jumpworld, She Who Weeps, Blue Light ‘Til Dawn, and Traveling Miles, but I find her album Coming Forth by Day (Legacy, 2015) both interesting and disappointing.  Wilson’s renovation of “Don’t Explain”—with a change of a few words—makes it more self-respecting, less masochistic, and that generates a necessary sense of power, just as the settings for some of the other songs add something unusual, even peculiar, but the collection does not have the kind of satisfying invention or vitality one expects or hopes for from Cassandra Wilson.  With an atmosphere that is moody, and self-conscious, “Billie’s Blues,” the most personal of songs, acquires a new distance rather than intimacy.  Yet the imaginative and expressive “Crazy He Calls Me”—“The difficult I’ll do right now. / The impossible will take a while,” Wilson sings—retains its charm. “You Go to My Head” is given an orchestral arrangement, with heft and swirl, and although Wilson’s voice sounds natural, especially in comparison with the production, there is an effect that is nearly one of alienation.  Wilson sings “All of Me” and, even after hearing it several times, I cannot recall how she sings it.  “The Way You Look Tonight” has an ethereal romanticism, and, in these circumstances, that seems a true trick of conjure.  The setting for “Good Morning Heartache” is one of pure artifice, giving the song an aspect of false theatricality rather than dramatic or metaphorical truth—and it suffers in comparison with the interpretation by Jose James, even though his does not mine the song for all its pain.  Wilson’s clear diction does help me to better hear the lyrics of “What a Little Moonlight Can Do,” but Wilson’s “These Foolish Things” is not memorable to me and her “Strange Fruit” has too elaborate and strange a treatment, verging on the psychedelic, followed by “I’ll Be Seeing You” and a nicely wistful “Last Song.”  It is time for the very intelligent music interpreter Cassandra Wilson to expand her expressive range, giving more attention to the exploration of emotion.

Audra McDonald has appeared on her own recordings—Way Back to Paradise (1998), How Glory Goes (2000), Happy Songs (2005), Build A Bridge (2006), and Go Back Home (2013)—as well as in theatrical productions for which she has won acclaim, such as Carousel, Master Class, Ragtime, Marie Christine, and A Raisin in the Sun, but she has done something brave and foolish and all the more stunning—she has impersonated Billie Holiday with conviction: Audra McDonald appeared as Billie Holiday in Lady Day at Emerson’s Bar & Grill (2014), directed by Lonny Price (for producer Tommy Krasker), for which McDonald won the American theater’s most prestigious and popular award, a Tony Award; and here is a 2014 recording of that musical performance, for PS Classics.  Audra McDonald recalibrates her large, trained voice to portray Holiday’s small and natural but strange voice.  It is a performance that can seem a little hard-edged at first, but one begins to believe in it.  Audra McDonald as Billie Holiday has a silvery singing voice that seems to come out of a whining pain, the rage to survive, and a desire for pleasure, as well as a spoken patter that is funny, rude, sentimental, tender, and wise—as Billie acknowledges the bitter facts of her life (the inability to perform in New York clubs and the public cynicism regarding her reputation).  Billie talks about family arguments and romantic disappointments, including the betraying and insecure man who introduced her to hard drugs, as well as the stupidity of racism, but also, significantly, about the obscurity of the songs many black singers performed—as the best material was given first to white singers (it was genius—or just honest and intense emotion—that the performers invested in the ordinary material, transforming it).  Some of the songs here are “I Wonder Where Our Love Has Gone,” “Crazy He Calls Me,” “God Bless the Child,” “Easy Living, “Tain’t Nobody’s Business If I Do,” “Don’t Explain,” and “Deep Song.”

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Daniel Garrett has written about art, books, business, film, and politics, and his work has appeared in The African, American Book Review, Art & Antiques, The Audubon Activist, Cinetext, Film International, Offscreen, Rain Taxi, The Review of Contemporary Fiction, and World Literature Today, as well as The Compulsive Reader. Author contact: or