Songfacts®:

• This Bill Anderson and Dean Dillon penned song was originally recorded by Anderson for the title track of his 2001 album. The following year, Kenny Chesney covered it for his No Shoes, No Shirt, No Problems set. Released as the record's third single, it peaked at #6 on the country chart.
• Dean Dillion considers this to be one of his favorite songs that he's ever written. He told us:
  
  "In my humble opinion, it's one of the best things that I ever had a part of. I know there's songs you write and you walk away that day going, 'Well, that's a pretty good job today.' Pat yourself on the back. I remember walking away that day after Bill and I wrote that thinking, Man, that's why you sit down and write right there, songs like that."
• Anderson and Dillon didn't know each other very well prior to penning this song, so they started off their session by having breakfast together, and talking about their lives. Anderson admitted to The Boot that he was envious of Dillon.
  
  "He had, kind of, what appeared to be, a carefree life, and I had had more of an uptight life," he explained." Before we even started writing the song, I said the opening line to him. I said, 'You know, I kind of envy you in a way. I wish I had gone out in the rain without an umbrella over my head a bunch of times,' and that's the opening line to the song: 'I'd spend a lot more time out in the pouring rain without an umbrella covering my head.' And that song just came out; that song just flowed, and we probably wrote it in a couple hours."
• Anderson felt that when Chesney recorded the song, he was still too young to fully appreciate its message. He recalled: "When we wrote 'A Lot of Things Different' in 2001, I was at the point then that I could look over my shoulder and say, 'Golly, I'd do that different if I had the chance to do that again.' You gain wisdom. I told Kenny - I may have made him mad, I don't know - but I told Kenny, 'Someday, you're going to know what that song's all about.' He recorded it young, and Kenny hadn't had the time to look back and regret things, and hopefully he never will. I was joking with him and kidding that, at my age, I've lived enough to wish I had done some things different."