There's a video on YouTube of Kip Moore playing a new song called 'New York City,' in New York City. The camera is anchored at his right from a balcony at the Bowery Ballroom, and it's clear that the acoustic performance isn't silencing this sold-out crowd.

Moore stands on stage undeterred in his everyman's uniform: dark jeans, red baseball cap and simple, thin chain that stretches across the absence in his dark v-neck t-shirt. Often, record labels and management groups don't like artists previewing new, unreleased material, but the singer likes to live with songs for awhile. It's not the only time in his career he's taken sound advice and thrown it in the garbage.

Take his outfit and standard for live shows and award show red carpets for example. The song 'Reckless (Still Growin' Up)' from his debut album 'Up All Night' explains how he got there pretty accurately, but Moore elaborated during a recent interview with Taste of Country. "I’m never gonna have a put-on for anybody,” he says.

Sonically, 'Up All Night' follows no formula, and the 'Beer Money' singer says the followup -- look for the first single in September -- will do the same. He speaks softly with a warm Georgian accent that's touched with just a pinch of Hawaiian surf. In song and in conversation, he oozes confidence without sounding arrogant. That's a requirement when you're pouring your heart out to a few hundred distracted fans in New York City.

"Sometimes, when you're playing a really rowdy club and you've been playing a lot of rowdy songs (like 'Somethin' 'Bout a Truck') and there's already a rowdy vibe in the place, you can't let yourself get discouraged if you're playing a tune like 'New York City' and you don't have everybody's full attention," Moore says. "But you can feel it with the few people … that you do have in the palm of your hand. You can tell if you have a big song, it's just gonna take people getting to know it."

Case in point: 'Hey Pretty Girl.'It just became his third No. 1 hit and is close to becoming his second Platinum single, but it took awhile. Moore knew from the moment he wrote it that he had a hit record, however. "I did, I honestly did," he admits. "It was the only one on the record that I actually did know that about."

The 33-year-old called ToC from a Toby Keith tour stop in Paso Robles, Calif. and spoke openly about the new project, touring with a legend and the song from 'Up All Night' that taught him the most important career lesson.

ToC: You have a unique, sort of progressing songwriting style on songs like 'Somethin' 'Bout a Truck' and a few others from the first album. It's different from the typical formula one usually hears.

Kip Moore: Yeah, I think the beauty of that first record and the second record is that I didn't write it with the so-called big writers in town. I wrote it with close buddies of mine and some that didn't even have publishing deals. There was a freedom in the room to do things the way that I wanted to and the way that I saw it. And there was a trust in the way we as co-writers were seeing it, not worrying about format and formulas and how it should and shouldn't go, like, "We can't go four verses without getting to the chorus, you can't do that." Well we were more like, "F---- it. Yeah we can. We'll do it how we wanna do it, you know."

Some songs I've been writing recently don't even have choruses. I throw a hook at the verses … I just don't like feeling like I have to write a song a certain way.

As far as the second album then, it sounds like we can expect to not know what to expect?

Yeah. To be honest, yeah. You know, I don't think that I'm doing something so crazy. But it's definitely gonna be a different record than the first. I think the first record was -- once you got past 'Somethin' 'Bout a Truck' and 'Beer Money' -- actually kind of a very vibey, chill record. It was a very nostalgic record. A lot of looking back on things, where this next record is more in the present. The titles are more in the present. The feeling of it is in the present.

It feels like on even your more upbeat songs there is some sort of natural pain hiding just below the surface. Is there some sort of heartbreak, or memory...?

You know … I think so. I think I've lived a pretty hard life. What I mean by hard is that … I've been kind of reckless with things. I'm a passionate person. I'm a super passionate person. I think there's definitely been sorrow in my life, good and bad. I think it comes through. I hope it comes through in my writing because to me that's what artistry is.

Are the rough times in your life self-inflicted?

A lot, yeah. I can be my own worst enemy for sure. Sometimes I can't get out of my own way. But you know some weren't and some were.

Have you ever had your heart broken?

Yeah, for sure. I think you haven't lived life if it hasn't happened to you at least one time.

Do you know 'Hey Pretty Girl' was gonna be as big as it has been?

I did, I honestly did. It was the only one on the record that I actually did know that about.

Your very first single 'Mary Was the Marrying Kind' didn't have much success at radio. Was there pressure to play it safe after that, and what did you learn from that experience?

I had so much belief that that song was gonna do well and I stressed over that song so much that I actually kinda said, "Ah, f--- it!" after that. I kinda said, "You know what, man, it's out of my hands. I'm just gonna put out what I wanna put out and just not worry about it."

I still care a great, great deal. But I refuse to let myself get so worked up and watching the charts and things like that any more and I just gotta have faith in what I'm doing and hope it works.

Are you an optimist?

Yeah, I think I am. I think I am.

A hesitant optimist?

Yeah, I kind of straddle the line of both to be honest. But I think at the end of the day, I usually have hope.

What does Toby Keith do differently than any other artist you've been around?

Man, I don't know if it's different than any artist I've been around, but what he does -- and when you watch all the people that were great like Garth Brooks, Chesney, Toby's got it too -- Toby brings you in to his world and you feel a part of it. You feel like he's one of you. It's such a fine art that so many people miss the boat on. I hope that I end up capturing that.

You've been compared to Bruce Springsteen, how does that make you feel?

Humbled. The Boss is the man. I've got a whole lot of career ahead of me to live up to that, but you know, I just write what I feel and I know it's gonna draw comparisons to some people, I've heard. Him, Seger, other people … and it's just a humbling thing.

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