Desmond described his own sound as something like a dry martini, and he wasn't wrong. His tone on the alto was unusually light and airy — no bite, no edge, almost no vibrato. Where Charlie Parker had made the alto saxophone sound urgent and combustible, Desmond made it sound relaxed in a way that somehow never tipped into lazy. His lines were long, unhurried, and full of unexpected melodic turns. He'd start a phrase, take it somewhere sideways, and land it so cleanly you'd almost miss how clever the whole thing was.

He spent the better part of two decades in the Dave Brubeck Quartet, which was the best-selling jazz group of its era. The partnership worked partly because their sounds were so different. Brubeck's piano was blocky and harmonically dense; Desmond floated over it. Together they pulled in audiences who didn't normally buy jazz records, and that success made some serious jazz fans suspicious. The fact that Take Five (1959) — which Desmond wrote — became a pop hit did not exactly help his critical reputation at the time. It was too catchy, too accessible. Looking back, that's a pretty strange thing to hold against someone.

Take Five (1959) deserves a moment here because it really is remarkable, not just as a commercial fluke. It's in 5/4 time, which should feel awkward, but Desmond's melody makes the odd meter feel like the most natural thing in the world. The solo he plays on the recording is unhurried, inventive, and somehow fresh every single time you hear it. A lot of musicians have written one famous song — very few of them wrote one this good.

His work outside of Brubeck tends to get overlooked, which is a shame. The recordings he made with Jim Hall in the early 1970s are especially worth tracking down. Hall's guitar was as understated as Desmond's saxophone, so the two of them together had this quality of conversation between people who didn't feel the need to fill every silence. Glad to Be Unhappy (1974) from that period is a good place to start if you want to hear Desmond on his own terms, away from the Brubeck framework.

He died of lung cancer in 1977, having left his Take Five (1959) royalties to the Red Cross. He had a reputation as a wit and a bon vivant — he was apparently very funny in person — and that personality came through in the music more than it usually does with instrumentalists. There's a lightness to how he played that wasn't accidental. He worked at making things sound easy, and if you listen closely enough, you can hear just how much effort that actually took.