David Nail: I don’t have anything to divulge! I met with my shrink last week so I’m all out, I’m all clean!

We’ll be easy on you. You’re opening for Alan Jackson tonight. How do you spend your day before a show?

When we’re normally in Chicago we’re a little closer to the city [instead of in Hoffman Estates at Sears Centre Arena] but usually I’m in bed the night before very early so I can get up and I’ll take the train into town with all of the locals. I just like to walk around the city, I like to do that pretty much everywhere I go. I love to go see the college campuses and stuff so if we’re in a town that has a school I’ll walk or get a ride to campus and walk around, buy a t-shirt or something. You hear these stories about people who fly in and out for shows and I just always felt like that would be very difficult for me because I feel like being in the place, seeing some of the behind-the-scenes stuff and meeting some of the people gives you a feel that you know where you’re playing and there’s a bit of a investment. It’s hard to really feel like you’ve got any sort of connection with the audience unless you’ve done that.

Do you have any pre-performance rituals?

I have tons of routines. I never like to eat within two hours of the show for obvious reasons and then from about an hour up to showtime if we do have guests we kick them off the bus or out of the dressing room and then we usually listen to music right until the guys have to go up on stage and get ready. We share a shot of Jack Daniel’s right before we go on.

We should have brought that!

Exactly! But there are also several little subconscious things that you do that you aren’t really aware of. For the first three years that I was doing this I’d take a nap everyday in the afternoon just because a lot of times when you play at 10:30 at night you’re used to going to bed at that time or you’re definitely not used to playing a show so it kind of turns the day around a little bit, especially if you’ve gotten up early. But on these shows we play around 8 o’clock so it’s really not that bad. Afterwards I’m a little tired and normally I’m ready to go and get in my PJs and have a couple of bottles of wine. Last night I was exhausted and in bed lamely by 11.

Country artists are known for being able to let loose and have a good time after their shows, but that’s not you?

I very much fit that definition. I have a philosophy generally in life and I feel myself referencing it more being out on the road and it’s just that life is too short. I never traveled much as a kid and that’s the best thing about this gig is that we get to travel around all over the place and meet new people. Especially out here in Chicago, we’ve been coming here the last four years so you feel like over the course of that time there’s been an investment on both sides. My friends here often joke that in four years I’ve mastered the city more than they have and they’ve grown up here and known it all their life but I’m very much a man on a mission. I’m that 33-year-old guy that looks like a 10-year-old walking down the streets looking up at the buildings. I grew up in a small town so I’m very much the tourist. I definitely have a few places where we’d go out here if we were a little closer to downtown. I still got a couple of things up my sleeve that I might try to use to see if I can manipulate myself over there tonight!

Where can we find you hanging out downtown?

Everybody that I know personally here in Chicago, where they go to hear music is to Joe’s Bar. We’ve got a great relationship with [the owner] Ed and [the music and production manager] Kelsey [Maynard], they’ve taken great care of us and we’ve gotten to meet several people. The [Bears] quarterback [Jay Cutler] has become a good friend of mine so a lot of times when we’re in Chicago we have to go to all of these secret places because he gets hassled too much and they’re places that are too fancy for me. I usually have a hat on so I’ll Houdini out of the back. But I love the Lodge. If I’m not at Joe’s the Lodge kind of reminds me of the places I hang out at in Nashville. I’ve done the whole Hub 51 thing and some of the nicer and trendier places but I’m a country singer at the end of the day and if I’m all hangin’ out at places like that I’m gonna ruin my reputation. 

How did you and Jay Cutler become so close?

He went to school at Vanderbilt and I’m older than Jay but Nashville is a very small community. One of his offensive linemen and really good friends got into the music business when he graduated and has escalated really fast so it was just from hangin’ out and seeing each other. There’s probably some other reasons why we’re friends. We’re a lot alike and depending on who you’re talking to that could be a bad thing or a good thing. He’s very stubborn, I’m stubborn. He’s very much a private person and I’m the same way. He’s just good. I’m obviously very proud of the season they’re having and when we played Joe’s he made an appearance and they were in Nashville playing this past week so my wife and I were probably the only two people in the Titans’ section with Bears stuff on.

Do you have a story that stands out as one that sums up your friendship?

It’s funny, when Jay got traded to the Bears he became really good friends with Greg Olsen who’s no longer there but it’s so bizarre because Greg Olsen’s from New Jersey and went to the University of Miami. You wouldn’t think he’d be a country music fan but he’s like the biggest country music fan in the world so they would go out on Sunday nights to Houndstooth and just get crazy. Greg doesn’t drink, he’s one of those guys where you would swear that he did because he’s just so outgoing and fun but I would get these calls at like 2 o’clock in the morning of them singing my songs at the top of their lungs.

You mentioned your wife Catherine, whom you married in 2009. What made you want to make her Mrs. Nail?

We’re all married and lame but one of our guys is single and I always tell him, “Man, when you can see someone at their worst moment and be so mad, like they couldn’t have pissed you off anymore, couldn’t have hurt your feelings anymore, you couldn’t be anymore disappointed and you know in that moment that five minutes later you’re gonna love ’em even more than you did before it happened, that is when you know you found the person.” My wife and I are going through one of those cheesy months right now where we miss each other all the time. We definitely have our ups and downs and I think my favorite thing about her and I always tell her and it sounds so cheesy—I can’t believe I’m even sayin’ it but I’m just in a good mood today—we joke about it all the time, we’re like, “You’re my best friend” or, “No, you’re my best friend” but she really is.

Are kids in your future?

We’re workin’ on that right now!

If you could have a drink with anyone, who would it be? 

That would change. Right now I’d want to have one with Mitt Romney just to see how truly pissed off he is but normally, and I’m not just saying this because we’re here, the only person that would truly cause me to have like a Beatlemania moment would be Michael Jordan. You hear all these great stories about people who party with Michael Jordan and I want to!

Photography by Isaac Joel Torres