By: Lauren Tingle

Jackie Lee was on a mission. He was determined to find me Dolly Parton’s Joshua in the Country section of pre-loved vinyl at Grimey’s Too. “It’s some of the best songwriting I’ve heard in my life,” he said. The search is part of No Limits Nashville‘s inaugural Music Monday game. I challenged Jackie to buy me three LPs that shaped him musically and I bought him three records that shaped me.

My search was quick. For Jackie, I grabbed Big Star’s Radio City, R.L. Burnside’s Ass Pocket of Whiskey and Al Green’s Gets Next to You. Jackie was having trouble finding his selections. Both Grimey’s and Grimey’s Too were out of his favorite entertainers, Frank Sinatra and Michael Bolton. Jackie asked a staffer at the register as my items were totaled, “Do you have any Michael Bolton?” Turned out both stores were low on inventory after a holiday rush.

I admit I was excited about Frank and a little skeptical about Michael. But we all have music that shaped us that others won’t understand. For example, I’m among the most loyal Hanson fans you will ever meet. I learned how to sing harmony listening to Middle of Nowhere on repeat all summer long in 1997. I called WMC-FM/Memphis every All Request Lunch Hour to request “Mmm Bop.” I binge-watched VH1 and MTV waiting for any Hanson news or music videos.

At the time, Internet was new, dial-up was slow and I was part of a dream demographic. I was a teen girl with nothing but time for music and cash from working a summer job at the mall. Give me flack all you want for my Hanson love. I’ll buy anything they make, and I imagine Jackie feels the same loyalty for Michael Bolton. Heck — Entertainer of the Year Luke Bryan is the biggest nerd for Lionel Richie you probably will ever meet. So, fiesta forever, haters.

Jackie searched for at least 30 minutes before settling on The Grand Illusion by Styx and James Taylor’s Greatest Hits.

I asked, “How were you first introduced to Styx?”

“My mom,” he said. “She was an ’80s pop girl and into all these hair bands. And Rod Stewart — one of my favorite songs to play on piano is ‘Have I Told You Lately.’ She would just listen to this stuff all the time. Dad didn’t hate it. He was more into Johnny Paycheck, George Jones and those guys.”

“And James Taylor?”

“He could make the guitar sound like a piano,” Jackie said. “The melodies he played, no one could ever figure it out. I’ve watched all kinds of live videos watching him play guitar and sing.”

“I interviewed him once on a red carpet,” I said.

“Was he short?”

“He was as tall as you with a hat on,” I said.

“Yeah,” Jackie said. “He always wears those hats. I’m glad you got those two. You have to have a Styx record. I’ll have to order you some Michael.”

Before the challenge, we coffee’d and enjoyed $3 cigars on the patio of Grimey’s Too. It was an unseasonably warm winter day, and the weather was perfect for an outside chat about his journey so far, his best creative advice and the longest 10 minutes of his life.

I want to know everything about your journey. Is it as you expected it to be?
No.

Didn’t think so. Is it ever?
No. That’s good because I think deep down we all want it to be easy. No one says, “I want it to be tough because I want to come out a better person.” I don’t. I’m still young and a lot of great things have happened. I’m thankful. But nonetheless, it has not been the easiest thing. My dad wanted to be a country artist really bad.

Really?
Dad is like walking country music encyclopedia. He can spit out any random fact. He just loves it. Deep down, he truly loves it. He moved to Nashville and spent about two years here just trying. He had things in the works and it all just fell through. My mom, just got really jaded and like really hated the music business. So, when they found out I wanted to be in it, and it was like, “Hell no.” Mom has always been supportive of me, but she just didn’t want to see me hurt like they hurt. Everything for me was going good. I graduated high school, and I was able to move here. I could support myself. I got a record deal with Republic Nashville. I got a publishing deal, and I was like, “What’s going on? This is cake!” And then lost the record deal. But I kept my head down and just tried to work hard. Then I met everybody at Broken Bow. And that’s been a good journey. Right now, I’m happy.

Talk about some of the first songs that you wrote when you first moved to town.
They were really bad.

Well, I have a girlfriend who mentioned the best piece of advice she’s ever gotten was write 500 songs in the first year and then throw them all away.
I tell you, Carson Chamberlain (Easton Corbin and Billy Currington), my producer, he’s the guy that I’ve known throughout my career. He told me my senior year to write a song a week. He said, “I don’t care if it’s ‘Yankee Doodle Dandy.’ Just write it and get it out of you.’ It’s repetition. It builds the muscle. It’s a muscle that you’ve got to work. I was just learning how to play guitar, because I played piano and drums my whole life. I started coming to Nashville to write with Carson and this guy named Steven Allen Davis. Some of the songs were really good. I don’t think I would use any of them today. It was a starting path. It is funny that you said that. Some songwriters will write about 1,000-2,000 songs in their life and 25 of them will be great songs. Other ones will be good but they’re not full songs that will ever work. So if it takes us three weeks on this first verse to make sure that every line is good, and then we build a song around that, we’re going to do it. It’s personal preference. Nonetheless, I wrote a lot of crappy songs to get to good songs. Benny Brown sat me down and said, “Hey listen, I like you. I like your voice, but I don’t like your songs.” And no one had ever said that.

They would sugarcoat it?
It just wouldn’t make sense to me. I appreciate direction.

Well, coming from a sports background, you get used to direction, “This is the play and this is how it has to be executed.”
Benny gave me a road map. He said, “I want you to find you. There are no limits on the songs you can write. Don’t try to write what you think is going to work. Just go write for your voice.” And so we did. A bunch of those didn’t work but a bunch of them did. It was the first time someone said, “Go be you. Quit trying to be whatever you think you’re supposed to be.” It gave me the confidence I needed as an artist. I feel a genuine belief behind what I’m trying to do. It’s not like it’s a feather in the wind. Just keep trying to make it work.

How long was your radio tour?
We were hot and heavy in October. When we started, we were hitting three stations a day, five days a week, on the bus. I think the longest we were on the bus consecutively was eight weeks. We went to Green Bay, Omaha, and all the places in between, too. We went to Sacramento, California, San Diego, Colorado, back home. So we made a loop around the country on the bus, which was unreal. My guitar player and I were like bugs on a windshield just looking at everything.

Was that the most country you’ve seen in your life?
The trip from Tennessee to Florida and then from Tennessee to West Virginia was about as far as I’d ever went. Getting to see all of it was nuts.

Talk about the life of a single and managing your expectations as a new artist. I’m sure there is a lot of music and concepts you’ve been sitting on that will carry over into a sophomore album.
It’s tough because you get so excited especially as a new artist. When you think about a single being on the chart for almost a year and that’s the only song that people know you for, you’re like, “I’ve got like 20 other songs I’d love for you guys to hear.” There are songs I’ve written and I’ve been pitched that I love. I listen to the demos all the time. But no one even knows they exist. I’m constantly thinking about that.

It’s tough for everybody.
Most artists are ADD. We’re constantly thinking, “What’s next?” So you have this mental obstacle to get over. I’m working on all this stuff but at the end of the day I’ve got to come back to my current single and work this song that we found eight months ago. It’s unique.

I also love what you do with “Amen.” I think that’s a gorgeous song.
We heard the demo and we didn’t know Love and Theft cut it. Benny goes, “We’ve got a problem.” I didn’t know they cut it either. He goes, “He goes look on your phone. When did they cut it?” That was their last record. He goes, “OK. We’re good.” It is such a great song. Even if dang Tim McGraw put it on his album, and didn’t put it as a single, it should have been a single.

What pulled you toward piano and drums?
They’re percussion instruments, and I’ve got to have a beat pushing how I feel. I grew up singing worship music, too. And what I love about singing worship music in church is that it’s really emotional. The drums and the piano are the two main instruments in almost any worship song nowadays. I think every kid is driven to the drums because they’re loud. But I was singing lead and playing drums at seven years old. My dad plays piano. I love the piano. I feel like I can sit down at the piano, play a song and know what melody to sing to have an emotional connection with someone.

So you’re self-taught?
My dad taught me like the basic chords on the acoustic guitar. But for me, I can listen to music and on the piano, find it, build the chord and go from there. I cannot read anything to save my life. I played saxophone in middle school band. When we’d get a piece to learn, I would go find it on YouTube and listen to it because I couldn’t read it. I would always fail my reading portion of the class, but I could play it. I just couldn’t read it.

Let’s go back to preparing for the Music Row disappointment. Was there anything your mom and dad said to you, “Ok…”
We had several college talks.

Where did they want you to go to school?
We never really got there because I was so against it. I told my parents, “I feel like if I was going to put four years in a school somewhere, that’s four years I could put into Nashville.” I’m glad they bought it because I meant it. But still I didn’t know it was going to work. I knew I was going to come down here and do everything I could to make it work. But mom was concerned.

You’re her child.
She also saw my dad and saw his dreams fall apart right in front of their eyes, and they did have a family. They had me when it was going on. She saw the disappointment that it brought to my dad. One day, he said, “Jackie, you have to understand something. This is the music business, and it comes with a lot of heartache at any point in your career. You have to be strong enough for that.” Losing the record deal and not knowing what was next, that was the first heartache that I ever really experienced in my life. So, I’m very thankful to say that it has been the toughest thing I’ve had to deal with. I feel like there are people who come here and spend decades trying to get a record deal. They’ll move here when they’re 17 and then they’ll be 40 before they know it and never had anything happen. So there’s not one part of me that will ever say, “Oh I had it rough.” No. Not at all. I’m just so thankful that it’s all happened the way it has.

What did you do in that time between deals to build up your confidence?
To be honest with you, the way I found out was my manager had a meeting with the label. We had a whole 12-song record done.

With Carson?
With Carson. Done. I had been sent three hard schedules of radio tour and they all got pushed back. And on the third one, they had a meeting. My manager said, “Hey can you come into my office?” He’s never said that to me before. I went over there and he said, “Well bud, they want to move on. And we’re no longer with them.” I just kind of sat there. I probably sat there for about 10 minutes. It felt like an hour. But it was 10 minutes and we didn’t say anything. And then I asked, “Well, what’s the plan of action?” That was how long I dwelled on it. I didn’t lose any sleep over it.

That’s amazing.
Why I’m so optimistic, I don’t know. But I was. Thank God. The hardest part was to call my parents. I told my dad first because I knew he would understand. I told mom that it was going to be ok. That was right before Christmas. It wasn’t a miserable Christmas break, but it was a tough because my family, they were all asking, “How are things going?” So I was answering all their questions, “It’s going good,” while lying through my teeth. In January I called my publisher at Universal and said, “I’ve been let go. I want to write five days a week. I want to write two times a day if I have to. Idle hands are going to destroy me. I’ve got to be working.” So much credit goes to them. They never said anything. They’ve always supported me and I was writing by January 10. I was writing three or four times a week. I’d pull double days every once in a while. Demoing songs left and right.

It toughened you up.
I needed that time to be honest. It absolutely made me a different person because I was dealing with things on my own. There was nothing dad could have done, nothing mom could have done and nothing a record label could have done. I’m so thankful for that entire time.

So are you going back into the studio and working on new music now, too?
It’s all demo stuff. It’s material I’m really stoked about. It falls into that pile of like, I’ll track it, send it to the label and they’ll be like, “Yeah! That’s great! But we’re working like 13 other songs that you’ve got.” It’s just the game.

You never know where those songs are going to end up, too.
You don’t know if another artist wants to cut it, which is never a bad thing. You always want songs for yourself.

I’ll never forget the number-one party I covered for Billy Currington and there was a new artist named Luke Bryan sitting next to him who wrote “Good Directions.” Here we are seven years later and Luke’s among the biggest stars on the planet.
Absolutely. It’s all a process. Songwriting now is my therapy. It gives my mind a chance to look into the future. It gives me goals to reach. What I love about Benny is that he believes in me long term. Any songwriting I do helps build the future, and it keeps me going. If I’m not on the road doing a radio appearance or doing a show, I’m writing.

How do you stay creative?
I have a journal. I feel like if my buddies knew I had a journal, I’d be destroyed. If I’m on an airplane, I’ll just write about whatever my day is like. It’s really good for me. I love to write. It doesn’t necessarily have to do with the song, I just love to write.

You do have a very interesting voice. Was there anyone you emulated growing up?
Michael Bolton. Yeah. I also get a lot of flack over that.

What was it about him?
Man, I don’t know. I just thought he was the coolest dude in the world. It’s so weird, because when I was growing up, he wasn’t the thing to listen to. I don’t know what drew me to his voice. But I would listen to YouTube clips of him and I would try to sound just like him. In high school, all I listened to was Keith Urban and Maroon 5. Adam Levine is my favorite. I want to get to a point where I can observe my music transforming. Listen to Luke Bryan. His first stuff was super country and what he’s doing now is still country. But it’s evolved. Tim McGraw — same thing. That’s what I want to do. I want it to be a process. But I definitely want Maroon 5, Michael Bolton and Bob Seger vibes to come through my music. I listen to a lot of Ronnie Milsap. We recorded over at Black River and I played his piano on my record. I was cutting my record in the same place he cut “Smokey Mountain Rain” and “Stranger in My House” and all those songs. That was incredible. It felt like a daunting spirit lingering in the room. Those vibes were there.

I want to see you play drums and sing, too.
I love doing that! When go back to East Tennessee and go to church, most of the time I’m out front singing. Sometimes they’ll let me play drums and I’ll sing. I love it so much. If people know me at all back home, they know me from singing in church. My dad and I had a little band. He would play keys and bass. I played drums and we sang. We toured churches all over the southeast. We went into Georgia and South Carolina, too, but we mainly stuck around our area in Tennessee. Ryan Tedder, he was a worship leader.

I didn’t know that about Ryan!
Tyler Hubbard from Florida Georgia Line was, too.

No way. Really?
I’ve never heard him talk about it, but Ryan did a full interview about worship music. There’s an instant gratification where people are instantly emotionally involved. And I want to try and bring that passion to what I do in country.

Which songwriters understand your style best?
I’ve been writing with Ashley Gorley since I’ve moved to town and that’s strictly because of Carson. Carson hooked us up. I think we cut 12 songs for the first record and nine of them were written with Ashley. He is just a mastermind and he came from the worship world, too. I’ve been writing a lot with Danny Horton, who works with Dan and Shay. Wade Kirby and Justin Wilson are others, too. I had a lot of strikeouts, too.

It’s like dating.
It’s so much like dating. In all fairness, you’re being intimate with someone…
…That you’ve never met before. How do you make sure you enjoy the moment?
I screamed that on the radio tour. I told every regional I was like, “I don’t want to be that guy.” You have those days when it’s a battle to get a song played and you get discouraged. But who gets to do this? Who gets to sit here, smoke cigars and drink coffee and talk about music for a living? I don’t ever want to be that guy who doesn’t enjoy every stage of life. My dad helps me with that as well. If he wanted to, he can choose bitterness but he loves music so much. He put that in my chest. The game is hard but you’ve got to love what you’re doing to play. That’s what keeps you going. It’s a love of what you’re doing, and I love being alive. I love being able to sing and I just love getting to do what I’m doing. My friend Ben Carver once said comparison is the cancer to creativity. That is so profound. I tell myself that all the time. Who am I to not be happy for someone in their life and encouraging to them when things are going good? I want them to be the same way when things are going to go good for me. You’ve got to live by that every single day.

Clearly you were raised with inexhaustible positivity.
I’m just really thankful for the house that I grew up in and the environment I grew up in. I’m very lucky and blessed to have my family.

Jackie plays the Belk Park Stage Sunday, June 14, at Nashville’s 2015 CMA Music Festival. The show starts at 2:05pm. Follow Jackie on Twitter and Facebook @JackieLeeMusic. His new single “Headphones” is available now.