Tim McGraw and his half-brother, Mark McGraw, played tourist in Philadelphia last week, allowing the CMT Insider crew to tag along. During their visit, the country superstar reminisced about his early days on the road, the first time he heard "Indian Outlaw" and the realization that "Don't Take the Girl" was a turning point in his career.

Editor's Note: CMT Insider will feature the first of a two-part series with Tim McGraw in Philadelphia on Saturday (July 17) at 1:30 p.m. ET.

Mark McGraw: Tell me about some of those early days on the road.

Tim McGraw: Well, it's been a great ride. I think that for me, what cut my teeth and made me a better artist and made me a better singer and made me a better performer were those years I spent on the road in a van, pulling the trailer. We'd show up at a gig and we'd play Monday through Sunday, seven nights a week most of the time. Sometimes we'd play two or three weeks at a place. It would be great to go to a place you'd never been before. On a Monday night, you set up and you're playing and there are 30 or 40 people there. Then word would get out about our band being there. By the weekend, it would just be jampacked and it would stay that way for the next two weeks that we were there. It was kind of cool to build a following and sort of build a reputation as sort of a bar band.

That's where "Indian Outlaw" started, your first single that really took off.

It was. "Indian Outlaw," from '89 when I put my first band together and started touring -- well, not "touring." We called it "touring" then, but when we started traveling, [it was] from gas station to gas station back then. ... We played everybody else's song and the one song of ours that we played was "Indian Outlaw." I heard that song the first night I moved to Nashville. Tommy Barnes played that song in a hotel for me, and I've played it ever since.

And the record label didn't particularly like that song.

Nobody liked that song when I cut my first album [released in 1993]. I wanted to do the song for my first album, but I couldn't talk the record label into letting me do it. But I did it for the second one for sure. I was going to make sure I did it the second time.

But the fans liked it and that's how you knew it came off, right?

The fans loved it. When we played clubs, we were just a small house band -- a four-piece house band that did a lot of cover songs. There were a lot better bands than us around, that's for sure. But for a song that nobody knew from a grab-yourself-up-from-your-bootstraps kind of band, and to be in there playing a new song and have to play it three or four or five times a night, it was a pretty good sign that it was a song that people liked.

If you could look back and compare yourself as an artist then to this day now, how do you see your career? How do you see how things have gone?

Well, they've gone better than I ever would have thought they would have gone. I've always felt like I was the kind of person who learned really fast. If there was something that I wanted to do, then I would pay attention and learn really fast. Music has always been a love of mine. I knew that this was what I wanted to make my career out of, and I knew this is what I wanted to do. I always felt like, given the opportunity to succeed, that I would succeed if I just had the chance to succeed. I've just tried to improve and get better every step along the way. Every time, I've tried to make a better record the next time around.

When did you realize that this was going to work for you?

I think there's always that little piece of that -- a little bit in your mind that tomorrow you're gonna wake up and be digging in the couch to pay for that pizza at the door. There's always a little bit of that. I don't ever want to lose that. ... There was one specific moment that I can recall when "Don't Take the Girl" had just come out. "Indian Outlaw" was a big hit, but we always had that thought in our mind that it was going to be one of those kind of songs -- if we didn't follow up with it, we would be gone tomorrow.

It might be a one-hit wonder.

Exactly, exactly. "Don't Take the Girl" had just come out, and we were playing this club in Houston. We played "Don't Take the Girl" and the club was packed. It was so packed that there were big-screen TVs out in the parking lot because they oversold the club. They had bars and everything set up in the parking lot. Darran (Smith, his lead guitarist) and I had started playing "Don't Take the Girl" and halfway through the song we had realized that the crowd was singing it louder than we were. I stopped singing and we just let the crowd sing the entire song. (We) looked at each other, and we thought, well, we might be able to pay our bar tab from here on out -- for a little while, anyway.

Mark McGraw is a CMT Insider correspondent.