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You grew up in Paris, Illinois. How does it feel to be back in your home state headlining at Joe’s?

Chicago is my favorite city in the world. Being here and being able to play places like Joe’s Bar after having lived here before is a beautiful thing. I used to come to these shows just to party and dream that I was going to be on that stage so it’s all coming full circle. Writing songs, having other artists record my songs and now having hit songs of my own and my own album, it’s crazy.

How was the experience of going on tour with Taylor Swift?

Going on tour with Taylor Swift is like going to school because she’s so good at what she does. If you want to learn how to fill a stadium and get a stadium’s worth of fans and beyond that, you watch how she works. She writes songs that connect with her fans and she treats everybody like they are her best friend. She really cares about her fans and she’s very smart. It was the Red Tour so the moment she rolled in she had all red trucks [and all of the details]. It’s all about the whole package for her.

What’s something you learned about Taylor from being on the road with her?

I was really surprised at how accessible she was. I was the first person to sing on the Red Tour last year and the first night I was about to walk on stage she came out and gave me this big hug and said, “Thank you for doing this.” I’m like, “Are you kidding me? This is nuts!” She’s one of the biggest artists in the world but she still stays so grounded. She’s awesome.

Who is the first person you call with good news?

My brother and I lived together when I first moved to Nashville. We’re very close still so I always share the news with him when things are going great or when they are not. My parents moved to Nashville to be around us, they are the ones who are always there for you and keep you grounded. Even tonight, I’m playing a show and I’ve got tons of family here.

Are you a Chicago sports fan?

Absolutely. I’m a huge Bulls, Bears and Cubs fan. I was just at a Bulls game last night, that’s my life.

Recent US99 Live Country acts include Blake Shelton and Sheryl Crow. At the age of 27, how does it feel to be singing in the same category?

Man, I love some of those artists. I think country music is in a great place. I’m actually on the same record label as Blake Shelton and Sheryl Crow and Blake helped me get my start. He gave me my first major show at the Ryman Auditorium and has been a great friend ever since. It’s really cool.

The first single off your debut album “Don’t Ya” reached number one on the country charts. You write nearly all of your songs. How do lyrics come to you?

Lyrics come to you in weird ways. Whether you wake yourself up in the middle of the night, roll over and then forget what you thought was the most brilliant line in the world or I’ve got songs that I’ve recorded on my phone all of the time. The really interesting ones are on a late night after I went out when I’m just mumbling into the microphone.

Are you seeing anyone?

No, I’m a single man! I’m not against having a girlfriend or anything like that but right now it’s just a lot of travel that I’m trying to get my head around. I’m very focused on my music but if it comes and smacks me in the face then so be it.

Biggest turn-off?

That’s a good question. My biggest turn off in a girl? Oh man, I don’t know how to do this without getting in trouble! I hate when girls hate on other girls for certain things. I like a girl who is really laid back and can go with the flow and do something random. Like if we’re playing a show tonight and I want to go on a date with a girl afterwards, we might not have a plan but let’s just go wing it or let’s go on a trip somewhere. I like that.

How many times have you been in love?

That’s another great question. Have I ever even been in serious love? That might not have even happened yet. I’m still waiting for that day.

Tonight could be the night. 

Hey, I might meet her tonight! I think it might be tonight!

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

Dead or alive?

Dead or alive.

Frank Sinatra. I think he was the coolest, smoothest guy ever. I just want to be half as cool as him. He was crazy as heck but he was awesome. I just love him.

What would you pour him?

Whiskey, straight whiskey. He liked Jack Daniel’s, which you would never think this guy would drink a Tennessee whiskey. In fact I have a special edition Jack Daniel’s Sinatra [Select] bottle. That’s what I would break out and say, “Let’s drink your own bottle of whiskey!”

Given the chance to make a cameo in any other artist’s music video, where would we find you? 

Katy Perry’s “Roar” video. I would do that one for sure.

Where are you the happiest?

I love playing my guitar at the beach. I grew up on a lake and I love the ocean. I just love being around water. I’m going to go for a little vacation in Puerto Rico for the New Year. I can’t wait to just wander around and go fishin’ and drink at little weird random bars that I’ve never heard of and no one knows.

KIRSTEN MICCOLI PHOTOGRAPHY

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