Elling grew up in the Chicago suburbs and came to jazz singing almost sideways — he was studying theology at the University of Chicago Divinity School when he started gigging seriously at the Green Mill, that old Uptown room that had been a mob haunt and was being revived as a serious jazz space. He never finished the degree, but the theological reading stuck. There's a reason his albums reference Rilke and the Psalms and Chicago street life in the same breath — that's not affectation, that's just how his mind works.

The voice itself is the first thing you notice. He's a baritone, but a flexible one — he can get dark and rumbly or open up into something brighter without it sounding like a gear change. He phrases like an instrumentalist, specifically like a saxophone player, which makes sense because a big part of his thing is vocalese: writing lyrics to existing jazz solos. He's done it to John Coltrane solos, Wayne Shorter solos, Wes Montgomery lines. When it works, it's genuinely impressive — you're hearing a human voice navigate lines that were written for a horn, with words that actually make sense as poetry. When lesser singers try this it sounds like a parlor trick. Elling makes it feel necessary.

His run of records on Blue Note starting with Close Your Eyes (1995) established him fast. The Messenger (1997) won a Grammy nomination and got people's attention nationally. Man in the Air (2003) is probably where a lot of people found him — it's got a version of Jon Hendricks's lyrics to a Coltrane melody that still stops the room. His working relationship with pianist Laurence Hobgood, who played with him for years in Chicago and beyond, is central to understanding those records. Hobgood isn't a flashy accompanist — he listens, and that gives Elling room to do strange things with time and phrasing.

He's also been willing to swing toward more accessible territory without it feeling like a sellout. Dedicated to You (2009), recorded with the Metropole Orkest, is essentially a Coltrane and Johnny Hartman tribute and it's gorgeous. SuperBlue (2021) goes after soul and R&B influence openly and landed him a new audience that hadn't been paying attention. Some longtime fans raised an eyebrow but the record is fun and it's not like he abandoned anything — he just turned up a different dial.

If you're new to him, start with The Messenger (1997) or Man in the Air (2003) and pay attention to how he handles the written poetry sections versus the straight swing. That contrast is the whole deal. He can be a little much — the literary references accumulate, the arrangements can get busy — but when the room gets quiet and it's just the voice and the piano, you hear why he matters. He's one of the few singers of his generation who sounds like he actually grew up inside the music.