Chesney and Mellencamp Hit 'Crossroads'

John Mellencamp talks about his life and career on the new episode of CMT Inside Fame debuting Friday (Oct. 3) at 8 p.m. ET/PT. Stay tuned at 9 p.m. ET/PT when Kenny Chesney joins Mellencamp to perform several of their biggest hits during a new episode of CMT Crossroads.

More than two decades ago, Kenny Chesney was just another small town kid sitting in front of a television in East Tennessee when John Mellencamp first caught his attention.

"This guy is standing up there … white T-shirt on and blue jeans," Chesney says, describing what he saw on the American Music Awards. "They were, like, rolled up at the bottom, and he had penny loafers on. He was singing this song called 'Ain't Even Done With the Night.' I didn't know who he was. I just knew I liked it."

Chesney acknowledges the influence by routinely closing his concerts with Mellencamp's 1982 No. 1 hit, "Jack and Diane." Proving that dreams can come true, he finally got to perform the song with Mellencamp during the recent taping of CMT Crossroads.

In an interview with Crossroads host Radney Foster, Mellencamp remembers appearing on that particular American Music Awards show. "That night, I was up there dancing and singing," Mellencamp says. "I was the young kid. I looked down and right in front were Michael Jackson, Diana Ross, James Brown and Chuck Berry." He adds, "But the next time I saw Michael Jackson, he had a pair of white socks and penny loafers. 'Hey, you've got my shoes on!'"

During Crossroads, Chesney and Mellencamp sing several of their best-known hits, including "R.O.C.K. in the U.S.A." and "Young." What really comes through, however, is the duo's ability to entertain an audience. As veteran performers will tell you, entertaining is not a talent that develops overnight.

"During the decade of the '80s, I was home, like, 22 months," Mellencamp says. "I can't remember the exact number, but the rest of the time I was on the road or making a record. On one tour, I did 149 shows. I had to actually have the name of the town taped in front of me."

Chesney can identify with the confusion of the road, noting, "You keep going so long … I was onstage and I found myself -- just for a second -- kind of going through the motions. That's not what people pay $65 to see. They didn't pay that to see you going through the motions. I caught myself doing it -- and I hope I never do it again."

Mellencamp adds, "The hardest thing when you're doing so many shows on the road is staying focused. Having a vision and staying connected to it … it's hard to do when you do that many shows. Particularly when you're singing songs, like in my case, that are 20 years old, 25 years old, and I've sung them a zillion times. How do you stay focused? Tonight [on Crossroads], we're doing 'Small Town' and it's a ballad version of the song. It's totally different. It's almost like a soul ballad, the way we do it."

Early in their careers, both Chesney and Mellencamp struggled until they took total control of their music and image. Chesney says, "I started to learn my audience and learn who they were. I was the one out there playing for them at night. When I kind of started taking creative control of my music is when I really tried to zone in and figure out who I'm really singing to."

In launching his career, Mellencamp's first record label changed his name to Johnny Cougar for the release of his debut album. It took years for him to finally revert to his real name after going through the transitions of John Cougar and John Cougar Mellencamp.

"I learned my lesson from Johnny Cougar," he said. "I'm a dumb hillbilly kid from Seymour, Ind., and I'm in New York. I've been rejected by every record company on both coasts and down here [Nashville]. I thought that was my one shot. When I came in and saw my first record, it said Johnny Cougar on it."

Adding with a hearty laugh, "But I have to say, the record wasn't any better than the name. So it really didn't make a hell of a lot of difference."

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