This duet with Willie Nelson is a cover of a 1949 standard made famous by Frankie Laine in 1949. Brian Wilson recorded That Lucky Old Sun around the same time as Chesney and like the Country star, also made it the title track of his 2008 album.
Chesney explained to USA Today that working with Nelson helped bring about a musical change in the way he recorded Lucky Old Sun. He explained: "Hanging out with him, I felt an artistic shift in a small way. This album isn't about a lot of guitars that are layered, and it's not about a very slick production. I'm letting my vocal lead the track instead of the track leading the vocal. These songs demanded that."
This was Willie Nelson's first chart appearance on the Country survey in almost five years. He'd previously featured on the list in early 2004 with another Chesney collaboration, the holiday song "Pretty Paper."
Barry from Sauquoit, NyOn December 7th, 1963, "That Lucky Old Sun" by Ray Charles entered Billboard's Top 100 chart; eventually it peaked at #20 and spent 9 weeks on the Top 100... Frankie Laine reached #1 (for 8 weeks) with it on Sept. 25th, 1949 on Billboard's Best Sellers chart... And on Billboard's Hot Country chart Kenny Chesney & Willie Nelson's version peaked at #56 in 2008.