Editor's note: Invitation Only: Kenny Chesney premieres Monday (Sept. 27) at 10 p.m. ET/PT on CMT. View a video of his performance of "Coastal."

Prior to taping his episode of Invitation Only, Kenny Chesney told CMT Insider host Katie Cook that he felt a little bit nostalgic by playing for such a small crowd.

"This is how I got started," he said. "I got started playing, as you know, on a stool with a tip jar. It's great to really feel the people listening to the music and to be right in front of them. I've always said that I am not a big believer in production. I believe music should come first. And every year I contradict myself ... but I do believe that music has to come first and songs have to come first."

During the one-hour special, Chesney previews his new album, Hemingway's Whiskey, including his latest hit, "The Boys of Fall." He also told the audience about the stories behind the songs. Here, Chesney tells Cook about preparing for Invitation Only and surprising his fans with the variety of his new material.

Cook: It's been a while since you've been in this setting. You have such a huge song catalog. How do you make a set list for a show like this?

Chesney: I knew we were doing 10 or 11 songs. I know that I am going to do five songs off of the Hemingway's Whiskey record that nobody has heard, so that leaves us five or six songs. We're going to try to make them cry a little, make them have fun. I'll try to take my two-hour show and condense it into five songs. That is tough, but over the years, I've figured out what works in this kind of setting. Even the really fast, rocking songs sound different in this setting. I'm looking forward to doing them.

It won't just be the fans that are laughing and crying. You get swept up in it sometimes.

Sometimes, this is an emotional ... being a singer and a songwriter, you have to feel that or you wouldn't be able to make somebody else feel that. So, yeah, I hope I feel that, anyway. I hope I never get tired of feeling that. That's what songs are all about. That's what writing songs is all about. So I hope the fans see that.

Let's talk about "The Boys of Fall." It's obviously about high school football, something very near and dear to your heart. What did you feel the very first time you heard this song?

I was on the bus with my guys out there, and we all grew up in a small town. In a place where not only football was a part of your life, but it was the thread of our life. Everything we did revolved around it. And I really believe that the smaller the town, the bigger football gets. That is how we grew up. I heard that song and heard the second verse, "little towns like mine" ... and that was us. I love the friends that have sustained me throughout my life, that I met playing football. We became friends that went through a lot together.

And, wow, so many people are going to be able to hopefully [have it] touch their life because there are a lot of guys that are still playing and a lot of guys like me that aren't able to play anymore. But there's also the mamas and daddies that are driving their little kids to football practice this time of the year. ... That is going to be a part of their life for a long time, hopefully. You know, watching them grow up, watching them go through high school. There is going to come a moment where they're not going to be able to do that anymore. That is what I thought about, too. It's more than just me liking high school football. I felt that this song was very parallel to the values we have in America, and I thought it was very powerful.

Let's talk about Hemingway's Whiskey. You've stated that this is setting the stage for a new phase in your career.

When I was done with Hemingway's Whiskey, I sat and listened to the songs, the production, just the overall essence of the record -- and it was a little shift. It's hard to put a finger on it. Hopefully, as you mature as a person, so does your music. I think as an artist, as a songwriter and as a person, the more you live, the more you bring in. Hopefully, that will reflect in the records that you make. I think that Hemingway's Whiskey definitely shows that.

Would that be a difference that the fans can detect, or is it just what you're feeling?I think more internal, maybe. Fans are pretty smart though. I think they are going to be able to hear a difference. I hope so anyway. ... Now, don't get wrong. Everybody says this is the best record I have ever made. And I got that, and I've said it before, too. I don't know if this is the best record I have ever made, but it's been a shift. I think the songs, song-for-song, are as solid as I've ever done. That starts with "The Boys of Fall." Songs like "Hemingway's Whiskey." There are a lot of chapters. A lot of ups and downs, a lot of having fun on here. Hopefully, a few songs that will make you think, miss somebody. I think there are some songs on here that people are going to be surprised to hear.

Really? In what way?

There is a song on here called "You and Tequila" that I love. It's very acoustic and it reminds me when I was on the road in 2007. I was incredibly exhausted, and I rented a house north of Malibu, Calif. I would turn off my cell phone a little -- I tried to, anyway -- but I would go down the PCH [Pacific Coast Highway] to this place with friends and eat dinner, have a drink or two and roll back up and watch the sunset. I did that for about a month. I was so exhausted from music that I really didn't want to listen to it, but when I had time and would turn the radio on, it was an Eagles song. It was perfect. Then all of the sudden I started listening to music again. When I heard the song, "You and Tequila," it took me to that spot. There is a girl singing with me. Her name is Grace Potter. She's just an incredible talent. When I heard this song, it took me to that drive, and it moves pretty good. It's not a stadium-type song that I would do. It's not a "Beer in Mexico." It's not a "Living in Fast Forward." It's not right in your face, but it's there. And that is OK, too. There is some of that on the record, and there is some stuff that is there in your face.

That is how I make records. But I do think there is something for a lot of people on Hemingway's Whiskey. I believe that people are going to have some fun. You'll fall in love, fall out of love ... want to play football again. They're gonna hopefully feel a lot of things.

Sounds autobiographical.

Always. You can't do what I do and not be autobiographical. You hope it is, anyway. That is what music is supposed to be. Be real. You can hide it all you want, but it always comes out.