Although her recording career has been somewhat erratic, Cassandra Wilson became one of the top jazz singers of the 90s, a vocalist blessed with a distinctive and flexible voice who is not afraid to take chances. She began playing piano and guitar when she was nine and was working as a vocalist by the mid-70s, singing a wide variety of material. Following a year in New Orleans, Wilson moved to New York in 1982 and began working with Dave Holland and Abbey Lincoln. After meeting Steve Coleman, she became the main vocalist with the M-Base Collective. Although there was really no room for a singer in the overcrowded free funk ensembles, Wilson did as good a job of fitting in as was possible. She worked with New Air and recorded her first album as a leader in 1985. By her third record, a standards date, she was sounding quite a bit like Betty Carter.

After a few more albums in which she mostly performed original and rather inferior material, Cassandra Wilson changed directions and performed an acoustic blues-oriented program for Blue Note called Blue Light Til Dawn. By going back in time, she had found herself, and Wilson has continued interpreting in fresh and creative ways vintage country blues and folk music up until the present day. During 1997 she toured as part of Wynton Marsalis Blood on the Fields production. Traveling Miles, her tribute to Miles Davis, followed two years later. For 2002s Belly of the Sun, she drew on an array of roots musics — blues, country, soul, rock — to fashion a record that furthered her artistic career while still aligning well with trends in popular music. Glamoured, released in 2003, posed a different kind of challenge; half the material was composed by Wilson herself. Unwilling to stand still, Wilson gently explored sampling and other hip-hop techniques for 2006s Thunderbird.