David Nail recalls Taylor tour, The Crown & the gift of small town innocence in attaining his dreams

Ian is an Arts & Culture correspondent for NPR & PBS Ohio affiliate WOUB, and Deep Ellum Radio host.

David Nail recalls Taylor tour, The Crown & the gift of small town innocence in attaining his dreams

Written by: Ian Saint

Photo by Michael Fogarty.

David Nail has accomplished several facets of what many consider “the dream”: multiple Gold singles (and the Double Platinum “Whatever She’s Got”), a decade-spanning major label discography, dream collaborations — Vince Gill, Brothers Osborne, Lee Ann Womack, and Miranda Lambert to name a few — and even touring with Taylor Swift (who tweeted that his “Red Light” was her “new favorite” song), including one of the future Eras Tour juggernaut’s first stadium headlining shows.

That is a far cry from Nail’s upbringing in Kennett, Missouri — located in the Show-Me State’s southeastern “Bootheel,” a tiny wedge jutting between Arkansas and Tennessee. But Kennett never strayed far from Nail’s heart. In fact, he released two EPs named Bootheel in 2020 and 2021; and his latest single, “The Crown” — the first release of a collaboration with Anderson East — was inspired by a Kennett classmate.

Upon losing his mother in November, Nail decided to scale back and hit the road as a one-man show — not just in performance, but also as his own crew and road transportation. The tour is called Down To The Studs, which characterizes both the astonishingly bare-bones operation and his embrace of vulnerability.

“In what has been the most challenging year of my career, both personally, and professionally, it became clearer… if I were going to continue in 2026, I had to clean the slate so to speak, and start fresh. What better way to start fresh, than to start over. This dream began with me, a guitar, and the songs. Just me, as raw, and real as the music can be. No band to hide behind, or to carry me each night. It’s just me, and I’m as excited as I’ve been in a decade,” he explained in a press release.

Nail spoke with Buddy Magazine’s Ian Saint from his Nashville publishing office between Down To The Studs tour legs, which hits Texas this week. Below is a transcript of their conversation, edited for length and clarity, following his Lone Star State tour dates.

IAN SAINT: Thanks for speaking with us at Buddy Magazine, the Original Texas Music Magazine, as you’re about to play several shows here in Texas. What memories and feelings come to mind as you’re about to traverse the Texas triangle for Down To The Studs?

DAVID NAIL: It’s funny. [When I first went to Texas] I was aware that there was a very unique territory down there — they have their own artists, they’re very loyal to those guys and gals. I [befriended] Mike Eli from the Eli Young Band, then Randy Rogers. I remember having multiple conversations with Randy about what made the Texas music scene unique — different from Nashville’s mainstream. Enough of a difference that when I finally started to go down there, I was terrified they were going to look at me as this outsider.

I remember [Randy Rogers] listening to my pity party, then him saying, “You know, D. Nail, if you just go down there and you’re your authentic self — not trying to be anything other than who you are as an artist… If they don’t like you, it’s not going to be because you’re from Nashville or some sort of superficial, ridiculous reason. It’ll be because they just are not into your music; it’s not going to be this personal vendetta.”

It’s a very unique place. The thing I love about Texas is depending on what city you’re in, you can feel like you’re in several different places — yet you’ve been in Texas for a week. So I’m excited to go down there.

IAN SAINT: One Texas performance that I’d imagine was memorable is playing Houston’s baseball stadium [then named Minute Maid Park, now Daikin Park] as you opened for Taylor Swift on several shows of her 2011 Speak Now World Tour. How does your memory of playing that massive show with an enormous production juxtapose with your feelings and observations as a one-man show on Down To The Studs? 

DAVID NAIL: That was the last show that I did with her, and the first stadium. Two things really stick out. The first one is, there was a rule that you weren’t allowed to record anything at any moment in time. This is when camera phones became legit for decent photography.

[When I arrived at the stadium] I remember Taylor’s dad riding a Segway up and down, talking to fans through the gates. It was the first stadium I’d ever been in, and I’m a huge sports fan; so when I walked in, opposite of the stage, I took a picture and sent it to my father — saying, “Can you believe I’m playing a Major League Baseball stadium?” Within 30 seconds, this guy was tapping me on the shoulder and said “Hey, I’m gonna need you to delete that.” I’m like, “Delete what?” “The video.” “Oh, no, I just took a picture.” “Yeah, you’re not allowed to do any photography.” Taylor was nowhere to be found; there may have been two [crew] people on stage. But I showed him, “Okay, I’m deleting this picture.” Granted, I’d already sent it to my dad. Then as I walked back, I noticed this big thing of blonde hair — and her mother was about 3 rows back at center stage. I don’t know if she knew who I was; I don’t think she really cared. But it’s hilarious  because I was [innocently] so excited about the baseball stadium aspect; I wasn’t trying to, like, record sound check.

The second thing is, you talk about how high budget [Taylor’s show was] — our performance was about as low budget as a stadium [performance] can be. We had, like, three floor monitors — it’s insane that we’re using floor monitors for a stadium show. We were all the way out on this thrust in the middle of the stadium. For sound check, the lights are all on; I could see we were high up — maybe 10 or 12 feet — and I’m terrified of heights.

For showtime, you walk down that long thrust and you can’t see anything; all you can see is lights from phones. I remember going to the edge and getting numb legs. I was shaking, and it wasn’t nerves; I felt like I was on this island, floating in the ocean. I had no sense of [stage] boundaries, so I was terrified. Luckily, we only did 3 songs. I remember getting off stage and saying “Man, I’m so glad that’s over.” [My bandmates] were like, “Man, were you really that nervous about playing a stadium?” I was like, “No, I was nervous about falling off the stage!”

From that moment forward, I have never played a show without floor monitors below me as a boundary, even though I use in-ear monitors. Like a warning track on a baseball field; if I kick that monitor, I know I’m too close [to the edge of the stage].

David Nail opens Taylor Swift’s Speak Now World Tour at United Spirit Arena in Lubbock on October 14, 2011.

IAN SAINT: Incredible. For context about “The Crown” — and really, your artistry in general — I want to talk about growing up in the Bootheel of Southeast Missouri. I’ve actually driven through there, and found it fascinating; this wedge of Missouri that’s south of Kentucky, slid between Arkansas and Tennessee. You’re smack between two rivers, the St. Francis and Mississippi Rivers, that are the state boundaries. What would you like folks to know about how growing up in Kennett shaped you?

DAVID NAIL: Yeah, where we’re positioned is sort of like a “no man’s land.” Far enough from St. Louis that it wasn’t a day trip. I guess you could sort of do Memphis in a day trip; but it was two hours there and two hours back — enough of a hassle [to hinder the worth of a day trip]. We never really traveled much of anywhere; and as a result, that kept me very sheltered — probably naïve to an extent. It was a very small town — almost all cotton farms when I was a kid — but we were the biggest town for an hour or so radius. All the other towns came to our town to cruise and chase our cheerleaders. So it was very unique from the standpoint of, I knew that it was small, but I didn’t have that sort of perspective because I’d never really been many other places. It really wasn’t until I moved to Nashville and got a record deal that I started traveling.

I have to give my father some props. My father was a schoolteacher and band director there [for most of] my life. He and our choral director, Viretta Sexton, had this unbelievable way of making art, music, acting cool things. It wasn’t until I became an adult that I’d heard the term “band nerd” or “choir nerd” — that was so foreign to me, because the starting quarterback would be in band outside of football season. It was never even [a consideration] of “Are people going to think I’m a dork if I’m interested in this?”

I’m really thankful. Even though I felt like God had given me music-related gifts, I had a really hard time choosing that for a career. Had I any sort of negative experience of exploring music as a kid, that would’ve been more than enough to keep me from pursuing it — but because I’d been around so many kids that loved it, that wasn’t the problem. The whole “I’ve got to move 4 hours from home and make huge life decisions at 18 years old” was where my issues were, not “Am I going to be a dork or made fun of if I try to do this for a living?”

IAN SAINT: Gosh, that’s beautiful. I can see how being siloed in this remote part of the country helped you to develop talents that might’ve been judged or elicited haters in a more “connected” area.

I was very touched by the story in “The Crown,” which portrays Lisa being the homecoming queen in her small town, but she went on to weather lots of dysfunction. Unfortunately, many rural areas have weathered tough socioeconomic trends in the last few decades; yet the beauty is still there. So my brain processed this song like a broader metaphor, and I don’t know if that was your intent. What has struck you about the reaction to this song?

DAVID NAIL: Without a doubt, I’d say 97-98% of the songs I’ve ever written always started with something very significant and true — something that I lived, some inspired by somebody I knew — then for the sake of the song, you may detour and it’ll take on a life of its own. Regarding “The Crown,” it’s as true as anything I’ve ever written. It was a very out of body experience writing it; then after listening to it, it was difficult to let it go any step further than just playing it for your publisher and people on the team.

I had to get comfortable with the concept of people hearing this and knowing who this person [inspiring the song] is, regardless of Lisa being her [real] name or not. Even if there are only 5 or 6 people that put together who I’m talking about, that bothered me enough to have this battle with whether I was comfortable releasing it. I feel like this song sort of speaks for itself; it’s very specific [in who inspired it], so I don’t know that I necessarily need to elaborate on this song any more than I already do in the song. From an objective standpoint of looking at it as a song, I feel like it’s very well written; but it is very difficult [for me] to remove the human side — this is something that happened and affected somebody that I grew up with. [Watching reactions to] “The Crown” is a bittersweet sensation.

IAN SAINT: I want to highlight the might of your past, too. I was blown away by the credits of your debut album, [2009’s] I’m About to Come Alive. The guitarist is largely Waddy Wachtel, who of course is Stevie Nicks’ guitarist; he went on to play with Jackson Browne, Linda Ronstadt, Carole King, James Taylor, Warren Zevon to name a few… he played guitar on Yes I Am for Melissa Etheridge, who’s up for Rock Hall induction this year. It’s incredible that your debut album is in that canon!

DAVID NAIL: You know, I have to confess that I didn’t know who Waddy Wachtel was at the time. I probably sat in this very room [at his publishing company] with Frank Liddell, who produced all my full-length records, and discussed musicians. The thing that I love about Frank is he’s produced all these legendary records for so many people, I think [people would assume] he’s got just this core selection of players that he trusts; but if you look at his work, for the most part, he changes it up. I think that says a lot about him, because it’s not something that he takes lightly — he really tries to put a lot of thought into, what do we hope to do?

I was, like, 28 years old making this record — my career depended on the success of it. This was my second try at a record deal, and there’s not usually a third. [Nail signed to MCA Nashville five years after Mercury Records released his single, “Memphis,” then shelved his album produced by Keith Stegall and John Kelton.] The first time I saw Frank’s name, he’d [produced the self-titled 1998 debut] record for Chris Knight; I remember obsessing with that record, and it was my first introduction to how “great” doesn’t always translate into commercial success, fame, tons of money or awards — when I got to Nashville, I would reference that record and everybody knew it. I wanted to make something that, if nothing else, people [decades] from now would reference that record as something of quality and respected it.

Man, the stories that we heard… Chuck Leavell played all the piano on that record, he’s got stories about being in Mexico or the Bahamas with Keith Richards. [Chuck Leavell was a member of the Allman Brothers Band in the 1970s, and has been The Rolling Stones’ principal keyboardist and musical director since 1982.] I’m listening to this stuff, and they’re talking about it so nonchalantly.

On the first day all those guys got together [in the studio], they’re talking shop; I kept going back to the kitchen, and there was a dozen Krispy Kreme donuts on the counter… I was so nervous and scared to be in the room, but also trying to listen, I kept going back and ate 9 of these donuts — and we’ve not even charted a song. [laugh]Thankfully, my metabolism at that point in my life was a lot better. I remember coming back after the first break, somebody opened the box and they’re like, “Who’s the fatty that ate all these donuts?” I’m like, “Uh, I saw lots of people eating donuts”; but the reality is it was me. [laugh]

I was still so young, dumb, and paranoid about keeping my head down and working… I wish I would’ve been more aware of how amazing [it was to savor the moment]. I mean, there’s a lot of stories I can’t tell; but I remember them talking about Jackson Browne, and the Eagles, and the vibe out in LA then. It was very surreal; almost those types of stories that now you tell somebody, and they think you’re full of crap and trying to impress — I’m like, “No, it really happened. I heard it from the actual person’s mouth.”

IAN SAINT: I can only imagine. That memory of the breaking point in your career brings it home to what you just shared about growing up in Kennett — being siloed in that remote small town was a gift to you and refining your talents. In that unbelievably surreal gathering for your first album, perhaps not fully processing the immense pretexts of who all was playing on that helped you to get the record done, and not get crushed by the weight of worry about impressing them.

DAVID NAIL: Absolutely.

IAN SAINT: Speaking of keyboards, do I hear Mellotron played on “The Crown”? It sounds like a cool homage to that ‘70s heyday we just discussed.

DAVID NAIL: You know what? It may very well be. That was the first song that Anderson [East] and I wrote, and the first song we recorded. I’d never worked with any of those guys, and never been with Anderson in the studio. So I’m in that period of the day where you’re like, “Do these people think I’m a schmuck? Do they even think this song’s good, or are they just playing [for a paycheck]?” And it went down very easily. Phil, the piano player, I’d heard a ton about over the years; so I was super excited to work with him. Everybody else got [their parts recorded] in one take; then Anderson works Phil for 45 minutes, asking him to play different sounds. So it very well may [include Mellotron]. It was an awesome experience — very, very different from what I’d done in the past, but super fun.

For David Nail tour dates and tickets, visit his official website: www.davidnail.com.

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