Vocal stalwart Kurt Elling, a Chicago music mainstay, talks politics and that Obama plant

Important update on jazz singer Kurt Elling: The plant that Barack Obama gave him as a housewarming gift, before he became a U.S. Senator in 2005, is doing well. “It’s up to my shoulders at this point,” says Elling, who bought the 2,300-square-foot Hyde Park apartment from the future president and his wife, Michelle. What kind of plant? “I don’t know,” Elling says, by phone from San Francisco. “Some foliage thing. Something that grows.”
Elling, 51, rents the apartment to a local family while he and his own family, his wife Jennifer, and daughter Luiza, split their time between New York and Chicago. He is on the road 185 nights a year, airing out “The Questions,” his recent album of jazz standards and unexpected rock and pop covers with co-producer and guest saxophonist Branford Marsalis.

The apartment changeover was not Elling’s only Obama encounter — he performed at a 2009 state dinner. And it’s not the only time Elling’s life and career has intersected with politics. He gave a 2015 interview lamenting “a cancer in the body politic,” adding, “There’s so much fear, and there are so many moneyed interests playing off of that fear.” “The Questions” is unusually political, as Elling builds the opening version of Bob Dylan’s “A Hard Rain’s A-Gonna Fall” to a piano-sax climax at the line “the executioner’s face is always well-hidden.”

He also hits a plaintive falsetto in Paul Simon’s dark and weary “American Tune” and adds death-obsessed Wallace Stegner and Franz Wright poems to jazz instrumentals by Stu Mindeman and Joey Calderazzo. In Elling’s unwavering, crystal-clear voice, the material is both bleak and hopeful. “Politics is always going to be a part of our experience — it might not feel as fraught as it does these days, but there’s always political suffering because of cruelty, and people in power taking advantage and people on the bottom suffering,” he says. “In a way, I feel guilty that I haven’t attacked issues like that earlier on and with more velocity.”

The most challenging thing about reproducing “The Questions” songs on tour is not replicating the emotion but remembering all the Dylan lyrics. “It’s basically a piece of really extensive list poetry, so without a specific storyline to remind yourself, or things that are going to rhyme in more logical ways, that can be a challenge,” he says. “But if you work hard enough and long enough and repeat it long enough, you can forget all the work and sing the music.”

Born in Chicago, Elling grew up singing in several choirs; his father was a church musician. In high school, he moved on to pieces by Carl Orff, Brahms, Handel and Bach. In college he emphasized jazz, as well as Rachmaninoff and what he calls “crazy Norwegian composers.” He says of his early training: “I’d be the only high school kid in a choir of 70 people — all these gray-hairs, and then there’d be this one dorky kid who really loved the music.”

Elling built his own scat-singing style, and by the early ’90s he was a fixture at local jazz club Green Mill. He signed with Blue Note Records in 1995, then put out albums of love songs (“This Time It’s Love”) and experimental reworkings of standards (“Flirting With Twilight”). He has become a master of vocalese, or the jazz art of inventing lyrics for instrumental compositions, as he does on “The Questions” by fusing musical compositions (Carla Bley’s “Endless Lawns”) with poems (Sara Teasdale’s 1920 “Winter Stars”) and his own words.

“As soon as I figured out what (vocalese pioneers) Jon Hendricks and Eddie Jefferson were up to … I couldn’t figure out where they came up with these astonishing melodies to sing,” Elling says. “As I continued to collect records and listened more broadly, I would stumble across the original Horace Silver composition and look at the dates and say, ‘Oh my God, they did that.’ It was like the penny dropped in the machine.”

In addition to touring for “The Questions” — the first of his upcoming Chicago shows is focused on Christmas music and the second is on the latest album — and Elling is planning what he calls a “radio-style drama” at New York’s Lincoln Center. It’s inspired by Joe E. Lewis, a Chicago comedian and singer who performed for Al Capone and other mobsters at the Green Mill in the ’20s — when Lewis left for a gig at a competing club, goons beat him nearly to death. Elling discovered the story as part of “Green Mill lore” as well as the 1957 Frank Sinatra film “The Joker Is Wild.” “The Big Blind” is scheduled to open in early March.

Interestingly, the hardscrabble, speakeasy side of jazz history is what made Elling’s father, the strict church singer, reluctant to support his music career early on. He’d grown up on the Illinois prairies among “very traditionally pious German Lutheran people,” Elling recalls, and learned about jazz from James Cagney gangster films. “He was weirded out,” Elling says. “His concerns were, ‘Well, Kurt, aren’t there a lot of prostitutes in the jazz clubs there?’ ‘Dad, no, there aren’t.’ As soon as he met actual people on the scene, he was fine with it.”