The first thing to understand about Lester Young is that he sounded wrong to a lot of people when he first came up. The reigning model for tenor saxophone in the 1930s was Coleman Hawkins — big, rich, muscular tone, lots of vibrato, harmonically dense. Young came along with something almost the opposite: a lighter, breathy sound, minimal vibrato, melodies that floated on top of the rhythm instead of pushing through it. When he auditioned for Fletcher Henderson's band in the mid-1930s, the other musicians reportedly didn't want him because he didn't sound enough like Hawkins. He didn't get the gig.

He found his footing with Count Basie's band out of Kansas City, and those mid-to-late 1930s recordings with Basie are still some of the best things he ever made. The band had a loose, bluesy swing to it that suited Young perfectly. He wasn't the kind of player who wanted to overpower a room — he wanted to float through it. Listen to almost any of his solos from that period and you'll notice how relaxed everything sounds, how he hangs back slightly on the beat, how he'll sometimes play the same note three or four times in a row just to make a rhythmic point before moving on. It shouldn't work as well as it does.

His work alongside Billie Holiday during the same period is some of the most naturally matched music in jazz. They had a rapport that you can actually hear — she phrases like him, he responds like her, and the whole thing sounds more like a conversation than a recording session. The small-group sides they made together in the late 1930s are worth tracking down if you haven't already. Neither of them is showing off, which makes the whole thing feel more intimate than almost anything else from that era.

World War II interrupted his career and did real damage to him personally. He was drafted in 1944, subjected to a court martial for marijuana possession, and spent time in a military detention barracks. By the time he came back to playing, something had shifted. The late 1940s and 1950s recordings are more uneven — sometimes he sounds distracted or tired, and the tone got a little rougher. But there are still great performances in there if you look. He was still capable of playing something quietly beautiful, and he never completely lost that signature way of sitting back inside the beat.

His influence on what came next is hard to overstate without reaching for words you shouldn't use, so let's just say this: the whole Cool Jazz movement of the late 1940s and 1950s — Miles Davis, Stan Getz, Lee Konitz, that whole relaxed, harmonically open approach — those guys were all listening to Lester Young. He figured out a way to play that didn't exist before him, and then a generation of players took it somewhere new. He died in 1959, the same year as Billie Holiday, which felt like the end of something specific and irreplaceable.