The superstar recently wrapped up a tour that put him over the million mark in concert attendance for the seventh consecutive year.
He's an Entertainer of the Year's Entertainer of the Year -- as the reigning title holder from both the Academy of Country Music and the Country Music Association, and having won it four years in a row from the ACM and three straight from the CMA. He's also this year's leading CMA Awards nominee, with seven nods.
Chesney, 40, has just released a brand new collection of songs. The album, his most personal to date, is titled "Lucky Old Sun."
Sure enough, one of its tracks, "Everybody Wants to Go to Heaven," was No. 1 on the Billboard country song chart for the week ending Oct. 18.
The new CD is "an incredibly personal record for me," Chesney told co-anchor Harry Smith on The Early Show Friday, "probably one of the most personal records that I've ever written and ever recorded. And, you know, I call it my "state of mind record,' Harry, you know? I'm in a lot of different states of minds the last three years! I think the music reflects it a lot.
"I'm just glad that it's finally out and people get to actually hear what we've been listening to on the bus for three months now so I'm excited about it! ... it's a very honest record. ... A lot of my reality is in this record."
Including reflections on his whirlwind romance with actress Renee Zellweger. Several songs on "Lucky Old Sun" are about the 2005 relationship with Renee Zellweger. They met that January, married in May, and broke up in September.
So, there's "no doubt" plenty of raw emotion in the new album, Chesney said, adding, "I think this is the first time as a song writer, really, that ... this is the first time I've actually let myself go that far and letting people in and see kinda what's been going on in my life a little bit."
He did the title song with Willie Nelson, whom Chesney says "inspired me more as a songwriter, as an artist, as a person, and I produced a record on him a couple of years ago, and we worked on this record together. I gotta tell you, you talk about inspiration! He can give you a lot of inspiration a lot of different ways."