Singer Kurt Elling at a crossroads

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Kurt Elling

Kurt Elling performs at the 2013 Thelonious Monk International Jazz Saxophone Competition at The John F. Kennedy Center for Performing Artsin Washington, DC. (Paul Morigi/Getty Images / September 16, 2013)

When singer Kurt Elling returns to Chicago next week, he will be dealing with two profound changes in his art and life:

Pianist Laurence Hobgood, who has been Elling's primary accompanist and arranger since they joined forces two decades ago in Chicago, will not be sharing the stage with him, for Elling has called a halt to their partnership.

And Chicago bassist Rob Amster, who toured with Elling from the 1990s until a few years ago, died suddenly last month of a heart attack at age 49, his death inspiring Elling to lead a tribute to Amster at the Green Mill Jazz Club early in the New Year.

Both developments have led Elling to ponder the nature of music-making and the fragility of life.

"I think that the thing with Laurence is part of a much larger transition time, where I've done a lot of things, and I'm 46, and it's time to really look around and see what the next act is going to be," says Elling.

"It isn't just one thing. It's about – for me, it's like, wow, I mean, I'm looking around, and what do I want to hold on to? And what's the most valuable thing? And how do I want to challenge myself? And I don't want to stagnate or take a break from challenging work. I don't want to take it easy. I want to figure what's really going to turn me on and challenge me for the next whole segment."

Yet considering the strong work that Elling and Hobgood achieved together, especially early in their partnership, why did Elling feel he needed to write the next chapter of his career without Hobgood?

"The chief thing, I think, is that Laurence is a magnificently talented creator," says Elling. "And talk about somebody with a signature sound and really all-encompassing technique and a breadth of musical knowledge that is really remarkable. And I really believe that he deserves and needs to be heard on his own terms.

"And I think it will be, over the course of time, I think it will be a growing sense of pleasure for him and for certainly audiences to have access to him as his own man.

"So for his sake, and for the sake of the music that he needs to make in his life – and so that I can have some adventures out here too, you know? I moved to New York (in 2008) for a reason, and it was so that I could be challenged, to move beyond my own comfort zone and to learn things and to be up-ended by several collaborators.

"So for me, and I believe that for Laurence, I believe it's a win-win. And really, I think of it just as a break in the action. And Laurence is one of my dearest friends in life. A lot of water under the bridge. And I look forward to the time when it's appropriate and joyful for us to reunite and get back to it."

Hobgood took a different view of the break-up when he discussed it with me last month.

"I think what has happened, for me personally, is a great sadness," Hobgood said. "I fully realize that I need to do my own thing and, to be fair, in the past I have not been as assertive as I should have been, availing myself of opportunities that one could argue were being handed to because of being with Kurt.

"And I know that has been a frustration for him, and that's fair. But to chuck the whole thing at a time when I just don't think it was necessary, I think it's sad. I'm going to move on and re-dedicate myself to doing the best work I can do for both myself and other fine folks that would like for me to help them sound good."

Fans of both artists probably shouldn't expect a reunion any time soon, for each is filling up his calendar with appearances alongside other musicians.

For Elling, that means collaborating with a variety of pianists over the next few months, including Gary Versace, Xavier Davis and Gerald Clayton.

"I don't really see myself locking into another long-term thing right away," says Elling.

But he's expansive in describing Hobgood's contribution to their music.

"On and off the stand, it's been extremely empowering, strengthening, from (Hobgood's) arrangements to having somebody there to back me up in rehearsals, or to run a rehearsal when I'm doing interviews," says Elling.

"It's been a massive contribution, and I'm proud of the work that we've done together, and I'm proud of Laurence for what he's brought to the table."

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The Grammys 2011