You just finished a sold-out run at the Café Carlyle in New York. Is this the first time you’ve done live shows on such an intimate scale?
Not really. When I moved to Nashville about 15 years ago, I started doing something like that, typically in the round. I would bring a little keyboard and sit down with a couple of other songwriters and we would just pass it around the circle.
Like they do at the Bluebird Cafe there.
Yeah, we used to do an annual charity event at the Bluebird, which I miss doing, with Gary Burr, Jim Photoglo, Mike Reid and myself. That was always fun, and it taught me a lot about performing the songs [in a stripped-down] way. It can be daunting because you have to compensate for the lack of instrumentation.
Your guitarist at the Carlyle was John Pizzarelli. How do you two know each other?
I’m one of his biggest fans. John and I share the same managers, which is how we met formally. I had seen him at Birdland in New York several years ago, and I just love what he did. His normal act is the consummate New York Rat Pack-style cabaret show, because he’s such a great musician. He does standards and jazz arrangements -- some really great stuff. And then he’s got such great stage presence.
You performed “Some Enchanted Evening” from South Pacific as well as “What A Fool Believes.” Given that both lyrics mentions fools and wise men, I’m wondering if those songs are connected in some way for you.
No, I think that just kind of happens. In fact, you just brought it to my attention. Well, you know, I draw heavily from that [Great American Songbook] influence. It’s one thing that John and I have in common. We grew up on a lot of the same music. My dad Robert was a singer and I was exposed to a lot of those songs growing up: Rodgers & Hammerstein and a lot of ragtime music, which, if you’re going to be a consummate blues musician – or at least have a deeper understanding of blues music – the ragtime era was where pop music started to be heavily impacted by African American influences.
Did your dad sing professionally?
No. He was a streetcar driver and bus driver when I was young. However, he worked his way up the ranks of the Bi-State Transit [which serves the St. Louis area] corporate structure to become an executive in the insurance arm of the St. Louis Transit Casualty Department. But he had a beautiful voice -- he was an Irish tenor -- and he was very popular in all the pubs and saloons in St. Louis. What he loved to do most was sing in saloons. I spent most of my time as a kid following him around from saloon to saloon to hear him singing. Eventually, I started playing banjo for him and we played together in a lot of clubs and saloons in the St. Louis area and civic events and functions. He actually sang for John F. Kennedy when he was campaigning to become president.
Do you see a connection between ragtime and more contemporary pop?
Whenever I sing blues from the ‘50s or the kind of blues that you might have heard Eric Clapton or Duane Allman emulate, I often feel the similarity of some of the ragtime stuff I sang early on. A lot of the phrasing and the harmonization is the same. And then with the Broadway stuff it’s just good. Some of that stuff, especially Richard Rodgers, is American classical music.
You have covered Motown classics on previous albums. Would you consider doing an album of American Songbook classics?
I’d love to. I love performing that stuff live, and it’s the kind of thing I’d love to do with John – to go out and play with some symphony orchestras around the country and do something a little more developed but similar to what we did at the Carlyle.
Moving on to your new Christmas collection and the tour you’re doing behind it --why do you love the season so much?
I like to celebrate the holiday season – not so much in a religious way, per se, but in a unifying way. For me, it’s a time of reflection when you look back at the last 360 or so days and think about the themes that are most important to us as human beings: what have we done to bring about further peace of mind for ourselves as well as the greater kind of peace and unconditional love that we should have for each other.
What I’d love to do is have you pick a few of the songs on the album and tell me why they’re special to you.
Okay, well, one of my favorite songs on the record is “Christmas on the Bayou.” We recorded it for [Through The Many Winters: A Christmas Album], which we did for Hallmark. That project was kind of dropped in our lap. Another artist, I don’t know who, was slated to do it and fell out at the last minute. We were handed the project on the condition that we could do it in two weeks. We said yes because, frankly, it was a wonderful deal they were offering us. So, I was literally coming up with arrangements of the traditional songs in my house – we had just moved into this place in Nashville -- and walking next door to the studio and laying down tracks. We were trying out things on the fly. For the most part it was just myself and Shannon Forrest, my co-producer, who’s also a drummer, making the tracks and then filling in the bass and orchestrations later. We literally did the whole record in two weeks: tracking, arrangements, production, mixing and mastering. It was a real hairy kind of project but it was a lot of fun for that reason too. In some ways, it was one of the best experiences of recording I’ve ever had.
And “Christmas on the Bayou” came from those sessions?
Yes. We went in and said, okay, what can we do that we haven’t done? I had always wanted to do a Cajun zydeco track, and Shannon Forrest had just finished a Cajun album with a well-known Cajun artist. We wrote the lyrics in maybe 20 minutes and the [music] as we were recording the track. The Christmas before, my wife had gotten me a Cajun harmonium that I had always wanted to use on a record. So, for all of those reasons, the song came to be.
Feel free to steer me to another song, but I love “Wexford Carol.”
Me too. That was written in, I think, the twelfth century in Ireland. I’ve heard it said that it was the first known Christmas carol as far as the history of Christmas carols goes. It was one of the first songs written about from a Christian perspective of Christmas and the story of Christmas. Which kind of intrigued me about the whole thing.
Your wife Amy Holland sings on the track with you.
It really suited Amy’s voice, which has a kind of Celtic, Kate Bush sound. I thought it would be a real good match for her.
Okay, give me another song that holds a special meaning for you.
I always dug the arrangement that we came up with for “Winter Wonderland/White Christmas.” It a bluesy big band kind of track, and Jim Horn did the horn arrangement. Jim and I go way, way back to the ‘70s. He was playing with [Joe Cocker’s] Mad Dogs & Englishmen tour and doing a lot of sessions in L.A. He’s one of the guys I met in my early experiences in California when I came out from St. Louis. It was just great to get a chance to work together after all those years, and there’s one horn in his arrangement that I just love. I wait the whole song for it. It’s such a hip little arrangement.
Your take on “O Holy Night” is pretty cool, too.
That song has a Brazilian samba feeling that I thought, in an unusual way, might really fit that song. I was sitting around at home playing it on the guitar and fell into that groove with it. And I though, you know, this works. I really enjoy playing that song live on the Christmas tour. I’m a real sucker for the Brazilian stuff.
You created the cover art for Season of Peace. Tell me about that.
That’s a pastel that I did. I did it as a poster for one of our Christmas tours a few years ago. The picture in its full size has another aspect to it that’s not on the cover because we couldn’t get the picture [to fit]. You’ve got this dead old tree in the dead of winter on the darkest night and a single set of footsteps leaving a symbol of peace for someone else to see. The peace symbol throws a long shadow, and the meaning is that every act of kindness has a ripple effect on all of us. In the darkest of times those messages are all the more important.
Do you have a favorite Christmas album, or is there an artist whose Christmas songs you particularly like?
I do love the Nat King Cole stuff, the classic Christmas records. There’s something about putting those records on and hearing his voice at Christmastime that brings back a lot of great memories of growing up. It’s funny how as we get older, what become our fondest memories are not necessarily the happiest times of our lives but the times of our lives that shaped us the most. For us growing up as kids at Christmas I know my parents struggled to even give [my two sisters and me] a Christmas. But there was something about that that brought us all closer together and gave us a sense of gratitude and appreciation that we probably wouldn’t have otherwise.
That’s for sure. While “Takin’ It to The Streets” could be interpreted as a political song, your best-known work is not known for making those kinds of statements. Is that intentional?
I comment on it from time to time on Facebook. I made some comments about [the Trump Administration’s] immigration policy and this bullshit of using the Bible to justify legally what’s happening. First of all, it’s a misinterpretation of the Bible. But stop and think about what we’re doing: We’re taking children out of the arms of their mothers and putting them in tents in the middle of the desert. And what makes that any different than any other horrific nationalist, fascist movement of the past?
What happens when you weigh in on subjects like that on social media?
The biggest hits I get on Facebook are if I say something like that -- and it’s usually very negative. There are a lot of venomous people out there that seem to have nothing better to do, but I’m very careful not to become one of the people that I have a problem with, because there’s a certain rabbit hole you go down in political discussions and other stuff where you just become as ugly as the ugliness you’re trying to confront.
Yes, I’ve encountered quite a few people who want nothing to do with people whose political views don’t mirror theirs exactly.
We’ve got to be careful in this country where the Constitution is just like the Bible. You can interpret it a lot of ways and a lot of people are starting to want to use it to protect the rights of the ruling party at the time.
That is certainly true.
[The Constitution] was meant to protect the people’s rights from any ruling party at any given time. We’re starting to really lose our grip [on that]. I thought that was happening with this immigration policy and said so – and I got a slew of “shut up and sing” replies. And I leave them on there. A lot of people I know they’ll get rid of the negative comments, like they’re getting back at those people. And I feel like I’m getting back at them more by letting those things sit there. And I hope they read them a couple of times so they can actually see themselves a little more clearly. Because I think some of them are so ridiculous, mindlessly obnoxious.
In other words, they’re more embarrassing for the person who wrote them.
Yes, so I leave them up. They do more damage to their own cause because I think that [the real] problem is that we start to think that everybody else is the problem—that we have no responsibility for what our problem is. So much of the politics and the pandering that this particular president is doing to a base that feels like they should have some kind of privilege. Look, I feel for anyone whose industry has been changed by the wrath of progress and time. Mine has, too. We’re all suffering from that, but the point is, a certain amount of acceptance has to take place that there is a new norm. [California Governor] Jerry Brown has talked about the reality of coal mining – not only the damage it does to the environment but that economically it doesn’t make any sense. So to pander to this whole region of the country that you’re going to bring back jobs that don’t really exist.
Because the industry is no longer sustainable.
Maybe you bring them back for a year. Those companies are only going to automate themselves. They’re going to get rid of these people anyway. All they want is the government money to retool. They’re not looking out for the best interests of these people and neither is Trump. He’s just looking for some reason to get a bunch of people riled up so they’ll vote for him. It’s like the government proposed that we start subsidizing the buggy whip industry. It makes no sense.
A version of this article originally appeared in the Nov. 10 issue of Billboard.