Cassandra Wilson

Cassandra Wilson, Toronto, October 1990

I ONCE ASKED MY MOTHER WHAT SHE THOUGHT ABOUT BILLIE HOLIDAY. My mom lived through the big band era as an adult, and saw bands all the time at local dancehalls like the Palais Royale and the Palace Pier. Her favorite singer was Bing Crosby. I was just getting into jazz and had heard a lot about Holiday, so I did something I rarely did as a teenager and asked her what she thought about music.

"I didn't like her," my mother said. "She had a lisp."

As a budding music snob learning about jazz, I'd end up avoiding vocalists, opting for the classic bias toward powerhouse drummers or tenor sax players, so while I eagerly sought out records by Elvin Jones or Coleman Hawkins, I'd vaguely mutter an opinion about how Lambert, Hendrick and Ross were "corny" or some such nonsense. It was probably Coltrane's record with Johnny Hartman that cured me of my silly aversion, but the singer who really brought me around to jazz vocalists was Cassandra Wilson.

Cassandra Wilson, Toronto, October 1990

Wilson came out of Steve Coleman's M-Base collective in the '80s, a group of young jazz musicians trying to navigate a path through the post-fusion, Marsalis-dominated jazz scene without creating retro jazz. She was, as far as I can recall, the only singer in the group, and the album that broke her big time was 1988's Blue Skies, a record of standards that showcased her husky contralto in a standard trio setting.

I played the record constantly in the loft studio apartment I shared with my then-girlfriend and her sister - so much that her versions of "Polka Dots and Moonbeams" and "My One and Only Love" are still my mental soundtrack to our long break-up. Wilson could have set herself up with a nice career doing standards in front of trios or big bands, but she decided to be a bit more interesting and followed it up with records that featured her versions of songs by Robert Johnson, Joni Mitchell, Hank Williams, U2, Neil Young, Jimmy Webb, and a really remarkable cover of the Monkees' "Last Train to Clarkesville."

Cassandra Wilson, Toronto, October 1990

When Wilson came to Toronto for a gig booked by promoter Serge Sloimovits at the Top of the Senator in 1990, I couldn't let the opportunity for a portrait pass. I don't know if I had a client for this shoot - I have a vague memory of getting my friend Tim Powis, then working at HMV magazine, to assign an article - but I turned up at the club at soundcheck with my lights and set up in a dressing room backstage. Perhaps Serge set it up for me as a favor.

I didn't imagine it would be a difficult shoot. I had a pretty good handle on my single softbox lighting set-up and cross-processed slide film, and Wilson herself was quite lovely, so I had high hopes for the shoot. The frame at the top was my favorite, then and now - the sort of elegant pose that I always struggled to steer my subjects into making, though it never really happened unless they found their way to itself. I know it was in my portfolio for as long as I had one, though I don't know if I ever managed to make a print with the particular warm tones I was able to get with this scan and Photoshop.

Cassandra Wilson has managed to produce an impressive discography in the quarter century since I took this photo, which included a long stint on Blue Note records. If you're anything like me, you'll start with Blue Skies and keep buying from there. At some point in the '90s I began collecting records by jazz singers, and haven't stopped.