There's no required order here either. Her catalog moves between jazz, blues, and folk without asking permission from any of them, and the songs don't care which shelf you'd file them under. Start wherever pulls you in.
In the 1980s, Wilson didn't sound like the singer most people would come to know. In New York, she was part of M-Base, a collective of young musicians led by saxophonist Steve Coleman that built dense, exploratory music aimed as much at other musicians as at an audience. Her early records lived in that world — ambitious, a little forbidding, respected more than loved.
Then, in 1993, she changed almost everything at once. Blue Light 'Til Dawn dropped the piano completely and brought in acoustic guitars and accordion instead, folding blues and folk songs in next to jazz standards. It could have read as a step away from the credibility she'd built. Instead, it became the sound she'd be known for the rest of her life — and it's still the easiest way into her catalog today.
New Moon Daughter (1996) pushed the same idea further and won her the first of two Grammys. She took songs that had nothing to do with each other — Son House's "Death Letter," the standard "Strange Fruit," even a Monkees song, "Last Train to Clarksville" — and sang them all in the same low, unhurried register until they sounded like they'd always belonged together.
A few years later, Traveling Miles (1999) had her writing and singing lyrics over Miles Davis compositions — one of jazz's great vocalists speaking directly to one of its great trumpeters, decades after the fact.
In 2002, she went home. Belly of the Sun was recorded in an old train depot in Clarksdale, Mississippi, in the heart of the Delta blues country she'd grown up in — the same roots that had been folded into her sound since 1993, this time recorded a few miles from where they came from.
Six years later, Loverly (2008) won her a second Grammy — built from jazz standards rather than blues or folk material. The songs are more familiar than what came before, but the voice underneath them is the same one she'd spent thirty years shaping: unhurried, low, unafraid of silence. It's that same signature, turned toward a different songbook.
Whichever one you start with, it's the same voice finding a new place to live each time.