The Enduring Lady Day

New albums from Cassandra Wilson and Jose James consider Billie Holiday's legacy on her hundredth birthday.

How many musicians are relevant at 100? Given how quickly styles and sounds change, it's hard to stay current for more than a decade, much less a century. Take Frank Sinatra, who was born in December 1915. Ol' Blue Eyes remains an icon, but Bob Dylan tributes aside, Sinatra sounds, well, old. Louis Armstrong? Still loved by musicians, but mostly known in the general public for his treacly late-career anthem to optimism, "What a Wonderful World."

Billie Holiday, though—she's got a claim. The artist, who would have turned 100 this month, seems to endure, even beyond Clueless references, which is all the more impressive given that she died in 1959, 56 years ago. Since her death, Holiday has been the subject of a film, starring Diana Ross; a play, in which she was portrayed first by Ernestine Jackson and last year by Audra McDonald (who won a Tony for the role); and countless tribute albums, including two particularly strong new interpretations of Holiday's catalogue timed to her centennial.

What accounts for her longevity? For one thing, she's arguably the greatest jazz singer ever. She's certainly the most familiar. Even people who can't tell Ella Fitzgerald from Peggy Lee know that voice, so recognizable and so difficult to describe. And as John Szwed notes in a new book, her myth is also an essential part of her continued appeal. There's her birth to a teenaged, unmarried mother; her rape and work in prostitution before her 14th birthday; her many marriages and entanglements; and her death. Most of all, there's her long battle with heroin, a struggle about which she was unusually open. For many listeners, one suspects, the personal life is inextricable from the professional. The pathos of Holiday's life seems to ooze out between the notes in her voice.

Unfortunately, one of the ways she endures is the appropriation and misappropriation of her most famous song. There was the public-relations firm that showed its utter lack of preparation for relating to the public by naming itself "Strange Fruit." There's Annie Lennox offering a tortured explanation of how the song is about things other than the lynching of African Americans. In a similarly controversial but more ambiguous example, Kanye West sampled Nina Simone's version of "Strange Fruit" and borrowed a lyric from it for "Blood on the Leaves," a track on Yeezus, which seems more like provocation than either tone-deafness or ignorance.

Alternately, some singers have opted to try to reproduce Holiday's sound. That's surprising, given how much importance is attached to Holiday's biography (who can hope to capture that sort of pain?) and given how hard it is to capture what made her so great—the phrasing and musical coloring and nuances. Imitating her strange tone enough to evoke Holiday is easier, and plenty of singers have drawn comparisons to her, from the lite-jazz of early Norah Jones to the twee jazz-pop of Madeleine Peyroux.

Against this landscape of lurid myth, imputed pathos, and imitation of the inimitable, two new records stand out as fitting tributes to Holiday that pay their respects by sidestepping the temptation to imitate. Instead, the two singers—Jose James and Cassandra Wilson—take songs from Holiday's repertoire and make them their own.

Like Holiday before her, Wilson has probably the most distinctive voice among jazz singers of her era—a sultry, sometimes breathy, and powerful one, with a powerful command of dynamics and phrasing. (Unlike Holiday's, it's a broad, thick sound.) She is also the most accomplished interpreter of songs in a generation. She's borrowed textures and songs from rock, folk, and blues throughout her career, and Coming Forth by Day is no different—her band includes T Bone Burnett and members of Nick Cave's Bad Seeds and the Yeah Yeah Yeahs.

It's by no means a rock record, but Wilson doesn't hold back in reframing and reworking the material. "You Go to My Head" gets a strong shuffle beat and a lush arrangement Phil Spector would approve of. "Billie's Blues" is a menacing Delta stomp. "I'll Be Seeing You" is slow and ethereal; Wilson takes her time coming in, and is barely above a whisper when she does. It might be my favorite Wilson record since 2002's Belly of the Sun; both prominently feature guitarist Kevin Breit. (Just like Holiday, according to nearly every account, Wilson has a magnetic stage presence, transfixing listeners and managing to wring genuine emotion from even the tritest standard. You can see and hear her excellent performance of selections from the disc at the Kennedy Center on NPR.)

Jose James's record, Yesterday I Had the Blues, is a little closer to Holiday's own sound—though he's a baritone, he can summon some of her piercing tone in his upper range, and he applies some of the strategic vibrato that Holiday made good use of. His record is also far more like Holiday's early sessions in form—they have the feel of a late-night jam session, rather than a heavily arranged whole.

James tends toward funky, R&B-inflected jazz of the Robert Glasper school, but Yesterday I Had the Blues sounds almost like a traditional jazz album—though there are electronic instruments—notably a slinky Rhodes electric piano on "God Bless the Child." Given that James's standard offerings tend toward funk and fusion, that's a little surprising, but the sparser arrangements offer a great chance to hear the band, an all-star cast of Jason Moran on piano, John Pattitucci on bass, and Eric Harland on drums. When I saw James play selections from it in New York in January, it was a high-powered, bluesy set. On wax, it's a much mellower mood, but it rewards repeated listening.

Since they're mining the songs most associated with Holiday, James and Wilson have significant overlap on their records. One of the songs that appears on both is "Strange Fruit," and the differences are instructive.

It's not the first time Wilson has recorded "Strange Fruit"—she gave a spare reading on 1996's Blue Light 'Til Dawn, a perversely swinging rendition backed by bass and some guitar and trumpet for accent. This time around, the melody is subsumed; beneath a steadily growing crescendo of strings and piano, Wilson gradually builds tension and volume, climaxing in a ragged guitar solo. This is epic music in the literal sense.

James's version bears practically no resemblance outside of the words. The song closes the record, and it leaves behind the rest of the instrumentation. He also alters the melody, but performs it over a background of a repeated vocal harmony and occasional—very occasional—handclaps. The casual listener may think of jazz as either quaintly swinging or arcanely pointy-headed. This is neither. It is unadorned and genuinely menacing, scary in a way that pop and jazz seldom achieve.

Political songs legendarily age poorly, yet even with listeners desensitized to "Strange Fruit," the song has acquired a painful and unwanted freshness in the age of Walter Scott and Eric Garner. It's a cliche of tribute records to say that the honoree would be proud of the product, and who can tell what Billie Holiday would want to hear? She was, apparently, a proud defender of the artist's prerogative to interpret, and she fought against any attempt at hiding the painful realities of life for black Americans. But the fact that musicians can find contemporary resonance in her music, and can interpret it in such radically divergent ways, shows why her legacy remains powerful after a century.