Kurt Elling talks tackling Frank Sinatra: Portland Jazz Festival 2015

There'll never be another Frank Sinatra. But we do have Kurt Elling.
The jazz singer will take on Ol' Blue Eyes' catalog at the Portland Jazz Festival on Friday, Feb. 20 with the Art Abrams Swing Machine Big Band, in a celebration of the year the American icon would've turned 100. With “Sinatra at the Sands” in mind and Quincy Jones' arrangements in hand, if there's anyone equipped to tackle Sinatra in the swingin' '60s, it's Elling. His two-decade career has drawn seemingly annual plaudits from the Grammy Awards — one win and 10 more nominations — and the DownBeat magazine's critics' poll, where if he doesn't win Male Vocalist, there's been a mistake.

We spoke with Elling to discuss standing in Sinatra's shoes, the late singer's legacy and his own international future.

You've been doing some Sinatra sets recently. What's been your approach to these songs, did you want to come to them more in your own style or stay true to his renditions?

Kurt Elling: What I try to do on the big band gigs is to certainly play a number of the classic arrangements that were created for Sinatra. We're talking about Billy May charts and Quincy Jones and Nelson Riddle. Those are like custom-tailored suits. In order to play those, or sing those stylistically, then you go down a certain road. I've done so much homework on Sinatra anyway as a jazz singer that I think a lot of that stuff comes out whenever I'm doing big band things.

At the same time, I don't want to just ape another artist. I can't outdo Sinatra at being Sinatra and I wouldn't want to try. So what I do as well is, I have a number of compositions that Sinatra recorded but that have new arrangements, and that allows me to be a little bit more myself and also to show how timeless the compositions themselves are.

Sinatra has his upbeat, swingin' side but also the more melancholy, “Wee Small Hours” side. Is there one that you prefer? 

KE: I think they're both equally emotional and moving to me. He projected such manhood of the era, 1950s, 1960s, the way that felt to be a brash American. And sophisticated at the same time. But definitely, (laughs) American machismo. And then the broken-hearted part is equally profound when you listen back to it because he really experienced all that. He experienced a lot of pain in his life and that came through with equal vibrancy and eloquence. So it would be tough for me to have to choose one or the other.

You mentioned doing homework. Have you learned anything new from doing these Sinatra-focused shows and standing in his shoes?
KE: I don't know if I've learned anything new but I've had it reiterated just how much fun it must've been to be Sinatra on stage and to have such great charts and to sing that stuff night after night. And how thrilling it must have been for audiences to hear that happen in a live setting.

Growing up and being a young musician, was he the person who inspired you or that you turned to?

KE: He wasn't the first one and he hasn't been the primary one. I've done as much homework or more on people like Jon Hendricks and Mark Murphy or Joe Williams — strictly speaking, the jazz stars. However, I'm not sure you could call yourself a self-respecting jazz singer and not have dug in as deeply as possible into what Sinatra did because that really defined a whole area of approach, especially in big band settings. Especially there. I don't know how you could sound good and not have some major influence from Sinatra.

Bob Dylan just released a new set of songs that Sinatra sang this week, I'm curious if you've had the chance to hear that.

KE: I've heard a couple of cuts online. I'm not sure what to make of it but you know, far be it from me to be a backseat driver on Bob Dylan's career.
Sinatra's music reaches beyond jazz, and especially for someone like Dylan to pay homage now — in 2015, why do you think his music is still so towering?

KE: Um, man, it sounded great (laughs). Sinatra's stuff sounds great and it makes you feel great. It comes with such technicolor bravado. Armageddon notwithstanding, there's not going to be a time when people aren't going to be wanting to hear some snatch of Sinatra. There are several occasions walking through your life when you want to celebrate and Sinatra's the way to do that.

As far as your own material, it's been a few years since we've had an album from you, are you working on any recordings or projects now?

KE: Thanks for asking! I'll be releasing a new project called “Passion World” this spring, and it's a number of things that I've been collecting around the world: from Cuba, from Germany, from France. Love songs from around the world that we've been reimagining, re-arranging, kind of trying to approach the rest of the world halfway. I do about 250 nights a year on the road — sometimes I get to hear other people sing. And when I do, I try to learn as much as I can about that stuff as well.

Anything else we should know about your Portland show?

KE: Well, I'll tell you this, I know that Bill Charlap is going to sit in with me on the gig and that's going to be a thrill. I just adore him, he knows all the right changes, his touch is fantastic, he's just an absolutely stellar, triple-A of a person. And that's going to be really nice. I look forward to hitting with him any chance I get.

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Kurt Elling with Art Abrams Swing Machine Big Band, Newmark Theatre, Friday, Feb. 20. 7 p.m.

The Bill Charlap Trio, Winningstad Theatre, Saturday, Feb. 21, 10 p.m.

Jazz Conversation: Kurt Elling & Bill Charlap in conversation with Will Friedwald, ArtBar & Bistro, Friday, Feb. 20, 5:30 p.m. Free.