Willie Nelson on His Frank Sinatra Tribute Album: 'Sinatra Had the Best Attitude About Everything'

Long before Willie Nelson's voice, braids and well-worn, well-loved guitar Trigger helped carve out the profile of an American icon, the outlaw country legend was learning how to warble and croon to the suave sounds of Frank Sinatra's records.

Hot on the heels of the April release of his latest LP, Last Man Standing, Nelson has laid a number of his favorite Sinatra standards to tape to honor his late friend, colleague and labelmate with My Way, out Sept. 14. The cover album is less a reinvention than a thoughtful meditation for Nelson, whose vibrato and viscous tenor fit right in line with a jazzy ensemble more attuned to Ol' Blue Eyes' lounge aesthetic than his own. Though Trigger's twang makes a cameo at a few points throughout, it's a fond exercise in nostalgia and appreciation, a faithful nod to beloved classics by a man who's recorded quite a few himself.

In a conversation with Billboard, Nelson looked back on his life-long appreciation of Sinatra's music, the process behind My Way and whether fans will be hearing these songs on his current tour, which wraps Nov. 25 in Sugar Land, Texas.

I know you’ve been a dedicated fan of Frank Sinatra’s for a long time. When was your first introduction to Sinatra? Are there any songs that struck you as favorites from early on?

Well, “My Way,” for sure. When I grew up listening to him, my sister and I played [his songs] together, and we learned all those early Sinatra songs. His great voice and his singing, I think, is what attracted us mostly to him, his phrasing.

We have so much to choose from when it comes to Sinatra cuts that would make for great covers. How did you narrow down your track list for this particular album?

Well “Always” was a natural, and we’d already done “Foggy Day” together, so I wanted to do that again. The rest of them, I just did the ones that I thought I knew best, that would be easiest for me to go ahead and record.

I’d seen the video you released of you recording “Summer Wind,” and the vibe seemed really chill in the studio. Did you change up your recording approach to My Way at all?

No, because I’ve been doing these Sinatra songs for so long, all my life. Sometimes I forget they’re not my music, too! I have to stop and remember, “Wait a minute -- these are Frank Sinatra songs.”

Did any click especially well, or become new favorites?

Honestly, I’d done them all so many times, I knew what I was looking for when I got to the studio, and I didn’t spend a lot of time there. I felt like, one or two, at most three takes, you got it, and if you hadn’t got it by then, you shouldn’t be doing it -- that’s really the way I look at the studio. I think a lot of people waste time in the studio, spend a lot of money, and the record costs a lot more than it should have. I’m not saying there’s not nobody tryin' to make that happen, but I do know that records can be made for less time and less money.

How do you set about making these classics your own? What was something, when you recorded this album, that you did to make sure you left your mark on these songs?

I think I did them the way I wanted them. Hopefully the Sinatra fans and the rest of the people will feel the same way! I’m really glad I did it. I’m glad it’s going to be out there. I hope the folks like it as much as I do.

What compelled you to make this record now? Did you just feel moved to make it in this moment, or did anything inspire you?

I’d been wanting to do it for a long time. I’m 85 years old. If there’s any better time to do it, I don’t know! (laughs) I think My Way is a pretty good time for an old guy to start singing.

You’re hitting the road again in September. Are these getting worked into your set list or have you played them yet in your current show?

No, I haven’t; I’m still trying to work some of the Last Man Standing stuff. There’s a lot stuff I do in the show I feel like I have to do every night and it’s a little difficult to put a new one in there. I’m gonna until the album comes out, the Sinatra stuff, and by then me and the band will know ‘em.

What is it about your music and Sinatra’s that makes the songs fit so seamlessly together? I know you mentioned he was an inspiration, but you were friends, too. What is it about the styles and structures that work well together?

We talked about phrasing and everything, but attitude is one thing, and I think that I’d have to say Sinatra had the greatest attitude about everything.

We could use a great attitude right now, frankly.

Absolutely. (laughs)

In difficult times, nostalgia can be a comfort. It can be something people seek solace in when facing a trying time. Is this a sentiment you identify with?

One thing I know for sure is that the fans like good music no matter what it is. They’ll drive a long way and pay a lot of money to hear people like me who they like to hear sing. They clap along, they have a good time and I think that energy exchange out there is the most important thing that happens.

You frequently work covers of your friends’ songs into your set lists. Are you interested in cutting another cover album?

I sure hope [to]. I don’t know right now what it’d be, but there’s a whole lot of places I could go and folks I could record and sing with that would be a lot of fun.

Is there anyone on your bucket list, in that regard? Anyone you’re hoping to perform with soon?

Well, I’ve been lucky enough to sing with almost everybody. Do you sing? I’d be glad to do a vocal with you. You’ll have to come sing with us.