In the Spotlight: Cassandra Wilson

In the Spotlight showcases a cross-section of an artist’s cover work. View past installments, then post suggestions for future picks in the comments!

As tradition has it, the jazz singer usually comes with piano accompaniment. Often, as with Diana Krall or Nina Simone or Norah Jones, the crooner is the keyboardist. The deep-voiced vocalist Cassandra Wilson broke this template back in the 90s. Her most successful music centers on the acoustic guitar, and features acoustic stringed instruments as main ingredients in the mix. If this unusual sonic palette makes Wilson’s music stand out, what makes it stick is her embrace of genres outside the jazz idiom.

Wilson first gained recognition in the mid-1980s as a founding member of the avant-garde M-Base collective. M-Base artists explored intricate rhythmic layering, free improvisation, and absorbing various African and African-American musical traditions, including newer branches like hip-hop. But Wilson soon struck off in her own direction, issuing several albums under her own name. Then she transformed her approach, and in 1992 she signed on with Blue Note Records (EMI).

It was at this point she expanded beyond jazz standards (and her own compositions) by covering folk, country, Delta blues, and pop material. From Hank Williams to U2, The Monkees to Van Morrison, Muddy Waters to Joni Mitchell, she was on it. At the same time, she began to feature instruments that were largely excluded from the jazz bandstand: classical guitars, octave guitars, resonators, banjos, a violin, a bouzouki, and a mandocello. Wilson redefined what jazz could sound like. She partnered with individualistic musicians (like Brandon Ross, Kevin Breit, and Charlie Burnham) all phenomenal artists who could play with imagination and with extended techniques. When Wilson herself played guitar it was usually in a “wack tuning” (to quote her own liner notes).

Not one to cling to a format or formula, she continued to evolve beyond her breakthrough Blue Note records (she left the label entirely in 2010). She even brought piano back into the mix, bringing to light some the best players of the next generation, including a young unknown named Jon Batiste. In some phases she focused on musical forms from Italy and from Brazil, or veered back into a more mainstream jazz approach, as on projects with Wynton Marsalis (the Pulitzer-prize winning Blood on the Fields production) and album-length tributes to Miles Davis and Billie Holiday. In the current decade Wilson’s been very quiet. She turns 70 in 2025, and if we are lucky she will re-emerge with more of her beguiling music to share.

Cassandra Wilson – Love Is Blindness (U2 cover)

Bono wrote this song for Nina Simone. Maybe that’s why it feels so fully realized when Cassandra Wilson sings it. I love the harmonics Kevin Breit plays on his resonator throughout this piece, and I love Wilson’s reading of the last line of the bridge: “Baby, a dangerous idea that almost makes sense”–how she starts off soaring and then downshifts to end so confidingly and with a hint of mischief. But what sends the song over the edge (no pun intended, none at all) is what follows that line, the cornet solo by Butch Morris. It’s strange, and yearning, and perfectly set up by his earlier playing behind the verses. Later the cornet mimics–with three or four notes–water droplets hitting the bottom of the deep well Bono wrote about. After a hundred listens, I never noticed them until just now.

Cassandra Wilson – Redemption Song (Bob Marley cover)

In the iconic version of “Redemption Song,” Bob Marley performs this anthem on his own, just the man and his guitar. Wilson follows suit, though she leaves the guitar work to Brandon Ross. Marley’s message is so clear and strong, understatement is called for. No one knows this better than Ross, whose playing and arrangements are always full of space and eloquent restraint.

Cassandra Wilson – Vietnam Blues (J.B. Lenoir cover)

Wilson grew up near the Mississippi Delta region where the delta blues originated, and she has been unique among jazz artists in her eagerness to engage with the form. She’s covered early bluesmen like Son House, Robert Johnson (twice), Muddy Waters, and Mississippi Fred McDowell. Here she covers a performer less well known even to blues fans, J.B. Lenoir. His “Vietnam Blues” is characteristic of his politically-charged take on the form. (It was fine for jazz artists and folk artists to meld their music with political protest, but for blues artists–not so much.) Wilson’s somber take on this weighty material is countered by the antics of her soloists (Martin Sewell and Kevin Breit) who take their licks and tricks to the edge of chaos. This recording was on the soundtrack to the Wim Wenders blues documentary The Soul of a Man.

Cassandra Wilson – Harvest Moon (Neil Young cover)

Lullaby-quiet and improbably slow, Wilson’s “Harvest Moon” still operates at extremes. The bassist bows the lowest note on the instrument, a long drone that never decays, while the resonator guitarist brings out the highest-pitched notes his instrument is capable of. (He does it by plinking the strings below and above the fretboard where you are not supposed to play.) The instruments establish a dusky mood and texture. A metal slide quivers against guitar strings in a wavering buzz, a sound akin to the chorus of crickets that opens and closes the track. Cassandra purrs out each line at her leisure, spacing each word just so. She strays so far from the original that it becomes a song of her own, not simply a Neil Young cover.

Cassandra Wilson – Skylark (Hoagy Carmichael cover)

This 1941 pop tune became a jazz standard that every singer has wanted a part of, from Ella Fitzgerald to Samara Joy. (Did you know “Skylark” is about Judy Garland? She was nineteen at the time, and lyricist Johnny Mercer was in love with her.) Wilson’s somewhat overlooked arrangement features the haunting pedal steel guitar of Gib Wharton–really, he is singing in tandem with Wilson through his instrument. And what a duet it is. Wharton was never part of the “sacred steel” movement but he brings the emotive element from that tradition into his free-ranging approach. Like everyone Wilson plays with, he sidesteps cliche and gets to what’s true, fresh, and gorgeous.

Cassandra Wilson – ‘Til There Was You (Meredith Willson/Beatles cover)

Composer Meredith Wilson had a long and storied career, from scoring Charlie Chaplin feature films to writing a Christmas song you know by heart. But for many, he’s only known for his 1957 Broadway musical The Music Man; for many more he’s only known as a song the Beatles covered. (Paul McCartney didn’t know it was a show tune when he learned the Peggy Lee cover from 1959.)

Cassandra Wilson doesn’t have the range of Peggy Lee or Paul McCartney and doesn’t need it. She has timing and feel on her side and, in this live version, a conversational tone. The ballad is a curious pick for a show closer, but what redeems it is Wilson’s ceding the stage to her young and largely unknown pianist, Jon Batiste. It’s a nice touch that after he solos, Batiste himself then leaves the stage so that the percussionist can play us out.

Cassandra Wilson – For the Roses (Joni Mitchell cover)

Joni Mitchell’s music made a lasting impact on Cassandra Wilson when Wilson was growing up in Mississippi. You can hear some of the influence in Wilson’s own lyrics, which often reach the pure poetry of the kind Joni had such a gift for. Musically, maybe it’s from Joni that Cassandra got into “wack tunings.” In this song about the dark sides of fame and success, you can hear that Wilson relates. “They start bringing in the hammers, and the boards and the nails” she sings with particular conviction. In addition to “For the Roses,” which was Wilson’s contribution to a Joni Mitchell tribute album from 2007, Wilson also covered Joni’s “Black Crow” on her first Blue Note release, Blue Light ‘Til Dawn.

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Cover Me is now on Patreon! If you love cover songs, we hope you will consider supporting us there with a small monthly subscription. There are a bunch of exclusive perks only for patrons: playlists, newsletters, downloads, discussions, polls - hell, tell us what song you would like to hear covered and we will make it happen. Learn more at Patreon.