Kenny Chesney Honors Childhood Hero in New Documentary

He Talks About The Color Orange: The Condredge Holloway Story

Kenny Chesney fielded a phone call from ESPN just a few days after finishing his first football documentary, Boys of Fall. They wanted to know if he’d consider producing another project spotlighting one of his sports idols, Condredge Holloway, the University of Tennessee player from the early ’70s who became the first black quarterback in the Southeastern Conference. Although the singer was looking forward to a break in his demanding schedule, he knew he couldn’t resist the offer.

“I was trying to figure out, ’Well, if I don’t do it, somebody’s gonna do it,'” he told CMT Insider host Katie Cook. “I’m so glad I did, though. It was a labor of love.”

Chesney premiered the documentary in Knoxville, Tenn., on Wednesday (Feb. 16), and ESPN will air it Sunday (Feb. 20). In this chat with Cook, Chesney explains his fascination with the football legend, his perspective as an interviewer and his reaction to meeting a childhood hero.

Editor’s Note: CMT Insider airs Saturday at 1:30 p.m. ET/PT.

Cook: Why was it such a big deal that he was the first black quarterback at UT?

Chesney: It was at a time when the civil rights movement was going on. Even as a kid, he didn’t really understand the way the world was changing because where he was from, it was all very much the same. He went to an unsegregated Catholic school. Everybody was together. He didn’t really understand all that until later on when he was in high school and there was separation. That’s the first time he realized that things were different. I think that it was a very big deal now because there are so many great athletes in the Southeastern Conference that still probably go through some of the issues that Condredge went through. But Condredge was the first guy that broke down the wall for some of those guys to be able to play the game like they play it today.

I didn’t know any of that was going on. I was brought up that you love everybody. That’s the kind of family I was in. … [Director] Shaun Silva was talking to me about why Condredge means so much and the racial issue, and I said, “When I was a kid, I didn’t see black or white, because he’s got the helmet on. I just saw the color orange and the No. 7.” I’d try to be that guy in the back yard. I wore the orange No. 7 jersey, and I’d try to emulate as a kid, as best I could, everything he did.

There’s a great school picture of you early in the documentary. Can you tell us about that?

(laughs) I wore the shirt because I loved Condredge. I wanted to have my school picture made in it. Everybody else dressed up wearing what you’re supposed to wear when you get your school picture made. And I showed up with an orange No. 7 Condredge Holloway football jersey on.

What was it like to be going out and interviewing people? You’re now the interviewer.

Yeah, I had to do my homework. I have a new appreciation for what you do, Katie. (laughs) The thing that worked the best about the Boys of Fall film and the Condredge film is that none of those people we interviewed, who are such a big part of the sports world, look at me as a member of the media. They looked at me as a buddy making a film about football that could touch a kid’s life somewhere. For that reason, they were very forthcoming. They were very emotional and honest, so I didn’t have to dig too much. They were all very, very, very honest with me and open. I don’t know if they would have done that for somebody in the [media] business.

You obviously saw so much of this footage as it was happening. But when you went back and watched some of his plays, was there anything that stood out and surprised you?

I do remember a lot of those plays, but you have to remember I was a little kid, so I didn’t really remember a lot of them. I remember seeing them vaguely, but over the years, growing up in East Tennessee and having Tennessee football in your life a lot, you see those plays sporadically throughout the years in highlights. But I had the opportunity to really dig through the archives and watch him, and it was incredible. … He did things in the early ’70s that a lot of the NFL teams and college teams today are trying so hard to find. They have this formation called the “wildcat.” Condredge did that years ago. There was one game that we used in the film when they played Georgia Tech and there is one play that Condredge scored on where every member of the Georgia Tech defense touched him. (laughs) But they didn’t tackle him.

It is like he danced circles around him.

Yeah, it was impressive to watch that and to see stuff I’ve never seen before. And to interview all the people that are a part of his life and made him who he is. And to interview his daughter and to interview everybody that helped make him the person that he is. I learned so much, and I’m so glad I did it. I’m so glad that the guy that I looked up to so much is such a great guy. And I never thought as a kid, when I was out in the back yard wearing an orange No. 7 jersey, that I was going to end up one day making a film about him. It’s interesting how life works out and what you get to do in your life. I would have never thought that I would be making sports films, but I enjoy the process and I’m passionate about it.

I think people who aren’t football fans are going to watch this just because of your involvement. What do you think that they will take away from this story?

They’re obviously going to see how passionate I am about sports, but I think that they are going to see a person that has clearly made a difference in people’s lives. I think that they are going to see that he did something special in a time when the world was changing, and he was able to come through it with a lot of grace and a lot of style and really didn’t want to focus that much on the fact that he was the first black quarterback in the Southeastern Conference. … And I think people are going to see how great of a guy he really is. The thing I love about it is that I got to make a film about my hero as a kid — and not all your heroes end up being great people. Condredge far exceeded my expectations as a kid of what a hero should be. He’s such a great guy, and I am really glad that my hero is a really good person.