Cassandra Wilson has received countless media accolades, including Time magazine’s 2001 pick for America’s Best Singer. Her smoky, almost carnal delivery is delightful. She’s an artist who likes the unusual and has built her reputation as a singer who likes to push musical boundaries, much like her musical influences: Joni Mitchell, Nina Simone, and Betty Carter.

Since 1993, Wilson has been an important part of the Blue Note label and has helped introduce jazz to a wider audience. Prior to signing with them, she was a well-regarded singer, but her critically acclaimed albums for small labels had left her slightly on the sidelines of the traditional jazz world. Blue Note gave her the budget, resources, and artistic licence to move forward and to make stronger statements.

It is difficult to choose between her 1993 Blue Note debut, Blue Light Till Dawn, and her sophomore release with the label, New Moon Daughter. Both are satisfying, but my preference lies with New Moon Daughter [Blue Note #32861], primarily because of the repertoire.

In 1995, Wilson travelled to Woodstock in upstate New York to record Blue Light Till Dawn. The studio was in a barn that had been converted years earlier by Bob Dylan’s manager, Albert Grossman. With her Harlem neighbor Craig Streets on board as producer, they recorded seven covers and five originals. Wilson’s blues-based compositions provide a glimpse into her southern heritage. “Little Warm Death” is a raw, powerful blues, accented perfectly with violin, about sex. “Until” is a song Wilson wrote in the hopes it would be used in the Arnold Schwarzenegger movie Junior. “Solomon Sang,” another original, is based on a story from the Bible about Solomon and Makeda, the Queen of Sheba.

Hoagy Carmichael’s “Skylark” is the highlight of the album, and Wilson sings it beautifully. She captures the essence of the song with a passionate statement about longing and melancholy. Her version of Hank Williams’s country classic “I’m So Lonesome I could Cry” is heartbreaking. “Strange Fruit” is a song identified with just one singer, Billie Holiday. Wilson’s rendition is bold and brave and massages the powerful imagery in the song. She is not without a sense of humour; completely out of left field is her playful version of “Last Train to Clarksville,” a song first performed by the Monkees. Wilson’s sensual reading of “Harvest Moon” makes it the long song that Neil Young had trouble communicating in his original.

Wilson is a great talent who moves in the jazz world with command and conviction. It is difficult to pigeonhole her musically. Her brilliance lies in blending songs from the worlds of rock, folk, pop, Tin Pan Alley, blues and jazz, in taking songs by U2, Neil Young, and Son House and mixing them with the standards of Billie Holiday and Hoagy Carmichael.

Miles Davis once said that for jazz to stay relevant it has to reflect the time it comes from. Cassandra Wilson knows it.