Kenny Chesney's Softer Side Country music superstar Kenny Chesney is a tireless entertainer who admits to being a workaholic, and claims he even sleeps better bouncing down the road on his tour bus, which is where fans can find him these days. Chesney will hit 22 cities on his "Brothers of the Sun" tour, which kicked off on June 2. The tour features his new song, "Feel Like a Rock Star," with Tim McGraw, reuniting the longtime friends on stage this summer. His new album, "Welcome to the Fishbowl," came out Tuesday and Chesney said its lyrics are his most honest and emotionally vulnerable yet. Watch "Nightline" anchor Cynthia McFadden's full interview with Kenny Chesney on "Nightline" tonight at 11:35 p.m. With 23 No. 1 singles, 10 platinum albums and over 30 million records sold, Chesney secured his place among country music royalty long ago. He travels with a fleet of buses and a 283-person crew. His last eight tours have each sold over 1 million tickets -- an astounding record. But Chesney took a break to spend the day with "Nightline" at his Nashville mansion, where he talked about his past and his future. Truth be told, the 44-year-old singer, who has won numerous awards, including the CMT Artist of the Year last year, has a mixture of qualities, beaming total self-confidence one minute and just a little bit of shyness the next. Chesney grew up a self-professed mamma's boy in East Tennessee. He had dreams of playing professional football, but his short stature was against him. The guitar didn't care how tall he was, though. Chesney first picked up a guitar in college and launched his music career in the '90s -- his songs have been played on country music radio stations ever since. As the years went on, the country singer said he has grown as a man and a songwriter -- and it shows in his music. Many fans can't help but hear his lyrics about love in the context of his famously short marriage to Oscar-winner Renee Zellweger. The couple was married in May 2005, but the marriage was annulled just four months later. Chesney later revealed that he wrote the song "I'm Alive" during their breakup, which he said was a difficult time. He and Zellweger don't talk, Chesney said, but with seven years of hindsight behind him, he has a new perspective on the experience. "I like to think that I've gotten better as a person," Chesney said. When you do what I do for a living and you're constantly moving and you're constantly creative, and you're constantly dreaming, which is -- that's me all the time -- finding a certain amount of balance in the middle of that is hard. Chesney has dated other women since his marriage, but at the moment, the singer joked that Pancho, his new goldendoodle puppy, is his only love. "It's interesting to date when you've already got a mistress, and my mistress is music," he said. But the country star hasn't totally written off the idea of marriage and having kids -- he is just not in a rush. "I don't even think about it," Chesney said of starting a family. I don't wake up every day and go, 'I feel like I'm missing something.' "As far as kids are concerned, you know, I hope it happens," he said. I love what I do. It consumes my life, but I will tell you that I don't think I want, forever, for my life to revolve around sound check at 5 o'clock and catering, every day. When asked if it was easier in some ways to have a relationship with an adoring crowd of 70,000 people instead of just one, Chesney took a few moments to ponder the question. "Believe it or not there's a very intimate thing about being up there with your guitar, the microphone and thousands of people in front of you and singing a song," he said. There's something in having them accept it and give back, because you know what? You give all yourself for two and a half hours and they give you everything for two and a half hours. But even with all the fame, money and acclaim, there was the uneasy sense that Chesney was still looking for something. "I'm never content," he said. You know how a shark always moves? I feel that way â¦ but there is a part of me that starts to wonder what I'm missing out on.