Singer Kurt Elling at a crossroads

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.”

In the meantime, following a New Year's Eve appearance at Northlight Theatre in Skokie and shows Jan. 3 and 4 at the Green Mill, Elling will lead a celebration of Amster's life at the Mill on Jan. 5.

Why did he want to be part of this event?

“Rob, and Rob's memory, deserves it,” says Elling. “He was a really great friend. … You don't just let a guy drop off the earth and not come together with everybody who knew him and loved him and respected him. You try to do it the right way.”

As for Amster's musicianship, “I just feel like he had all the hallmarks of what a jazz musician wants to be and what you want a jazz musician to be,” says Elling. “He had a signature sound that was immediately recognizable. He had an extremely high level of craftsmanship and dedication to everything, (such as) swinging really hard. … But he could also solo with a beautiful sense of architecture and clarity and excitement.

“And he knew the history of the music. He was interested in the history of the music. He wanted to be a part of it. He knew all the jokes and the inside stories. There was just no down side.”

Says Mike Amster, the bassist's father, “Everybody is calling it a memorial, and I said, 'I want you to stop calling it a memorial. Start calling it a celebration.'

“For the most part of his life, he had a terrific life. He loved his music,” adds Mike Amster. “I know there are a number of musicians that want to come, that have played with him, that want to come and play. I think it will be a kind of a jam session. I know Kurt wants to say a few things. I may say a few things.

“Just basically for his friends to get together and remember the good times.”

Elling, meanwhile, says he's purposely slowing his touring schedule in 2014 as he tries to catch his breath after two decades of relentless traveling and the toll of life on the road.

“I've gotten to see a lot of the world, and I've gotten to make friends throughout the world with my voice, to have really deep and rich experiences with my bandmates and with Laurence and with, man, so many great musicians we've met out there.

“It's also been challenging physiologically to be on that many airplanes. I mean, I flew 100,000 miles this year between Jan. 1 and July 1, which was tiring. That's when it really got out of hand.

“And, you know, it's a sacrifice for my family to make,” adds Elling. “It's a sacrifice for me to make, being away from them, which is another reason why I want to take a little break.

“Luiza is 8,” adds Elling, referring to his daughter. “And I don't want to be the father, you know, she grows up and says, 'Yeah, my dad was never around, so I never got to know him very well.' That's not for me. I want to know her, and I want her to know me, and I want to be around. … Now my hope is to plan touring and appearances in such a way that I'm not just taking every gig, and I'm not just scrambling around.”

Along these lines, Elling has been developing a theatrical piece that he describes in an email as “a new fictional story loosely based on the life of (singer-comic) Joe E. Lewis,” who had his throat slashed by Chicago mobsters and lived to tell the tale.

If Elling can get the work on its feet, might he find himself spending less time on the road?

“That's part of the hope,” he says. “I'm certainly writing it as a performance vehicle that would allow me to expand my audience into the realm of people who check theater out more than jazz. … It carries with it the possibility that I can sleep in my own bed, with my own wife, night after night.”

Thus begins the next phase of Elling's story.

Kurt Elling performs 8 p.m. Dec. 31 at Northlight Theatre, 9501 Skokie Blvd., Skokie; $75-$125; 847-673-6300 or northlight.org. Also 9 p.m. Jan. 3 and 8 p.m. Jan. 4 at the Green Mill Jazz Club, 4802 N. Broadway; $15; 773-878-5552 or greenmilljazz.com. And Elling will appear in a “Celebration of Rob's Life,” honoring Rob Amster, 1 p.m. Jan. 5 at the Green Mill; no cover charge.