Story Behind the Song: Kenny Chesney, ‘A Lot of Things Different’

Kenny Chesney earned a Top 10 hit with the song "A Lot of Things Different," the third single from his multi-platinum 2002 album, No Shoes, No Shirt, No Problems. The tune, written by Bill Anderson and Dean Dillon, waxes poetic about regrets in life and the longing for second chances to make different choices. Below, Anderson tells The Boot about the day he and Dillon wrote the song that speaks to Anderson more than any other he has written.

Dean Dillon and I wrote it together. We didn’t know each other very well, and we had breakfast together, and then by the time we got over to his office to try and write, all the barriers were down between us, and we could write a pretty honest song. We got to talking about our lives and the fact that I was close to my father and he never knew his father.

In a way, it was magic, because I envied his life: He had, kind of, what appeared to be, a carefree life, and I had had more of an uptight life. 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.

When we wrote "A Lot of Things Different" in 2002, 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.

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