If you're coming to Carla Bley for the first time, the best place to start is probably Escalator Over the Hill (1971), the sprawling double album she composed and produced over several years with lyricist Paul Haines. It's a jazz opera, sort of — it also has rock, Indian classical music, and a cast that includes Jack Bruce, Don Cherry, and Gato Barbieri, among others. It is genuinely strange listening, and it shouldn't work as well as it does. But somehow the whole thing holds together through sheer force of compositional personality. Bley has a way of making chaos feel structured without draining the life out of it.

She grew up in Oakland, California, and moved to New York as a teenager. The story of teaching herself harmony and theory while working as a cigarette girl at Birdland is true, and it matters — she was absorbing the music directly from the room rather than from a conservatory. She married Paul Bley in the late 1950s and became embedded in the downtown New York scene that was pushing jazz into new territory. She co-founded the Jazz Composer's Orchestra with Mike Mantler, who became her long-term partner and collaborator, and together they set up JCOA Records and later WATT Records to distribute their own work. That kind of structural independence was rare then and it shaped everything she did afterward.

Her piano playing tends to get overshadowed by her composing, which is understandable but a little unfair. She's not a virtuoso in any conventional sense — she plays with a kind of deliberate economy, leaving a lot of space, and her touch has a dry, almost sardonic quality. It fits her compositional voice perfectly. When she leads her own groups, the music often has this wry, slightly theatrical quality, like the band is in on a joke that takes a few listens to fully get. Dinner Music (1977) is a good example — the title is a bit of a gag, but the music is genuinely sophisticated and more accessible than some of her earlier work.

Through the 1980s and beyond, she led various configurations of what became known as the Carla Bley Band, and she also did a lot of work in smaller settings. The collaborations with bassist Steve Swallow, her partner since the early 1980s, produced some of her warmest and most direct music. Duets (1988), recorded with Swallow, strips things back to just piano and bass and lets you hear how much personality she gets out of a relatively simple setup. She's also written for big bands and chamber groups, and the writing is always recognizably hers — you could pick a Carla Bley chart out of a stack without seeing the cover.

What makes her worth spending real time with is that she never made a career out of being difficult. Some of the avant-garde composers of her generation can feel like they're daring you not to enjoy yourself. Bley's music has humor and swing even when it's being structurally adventurous. She can write something that sounds like a children's song and make it feel completely at home next to something dissonant and gnarly. That range, and the consistency with which she's maintained it across six decades, is the thing.