Songfacts®:

• In this song, Brad Paisley is imagining he is writing a letter to his 17-year-old self. He reflects on people and moments that have shaped him, and tells his teenage self what he has learned over the years.
• One of the lyrics refers to Linda Brinkman, who was Paisley's public speaking teacher and was a great help in the Country star overcoming performance anxiety. He recalls in an interview with the North County Times June 27, 2007: "There's a line in the song that says, "And you should really thank Mrs. Brinkman." She was - and still is - the speech teacher at John Marshall High School. She told me, 'You have to take this class. When you get up with a guitar you're fine. But you need to know how to talk in any situation to a group of people if you really want to do this for a living.' It was a pivotal time in my life."
• In the same interview Paisley discloses how his baby son influenced the writing of this song: "As I wrote it I saw a second chance emerging in the song, and the second chance is epitomized in the fact that I have a son now. When I wrote it, I didn't know if we were going to have a boy or a girl. Maybe deep down I knew all along."
• The video for this song was filmed at John Marshall High School, Paisley's alma mater in his hometown of Glen Dale, West Virginia. It features some of his classmates from 1991 when he was 17, and some contemporary students from the school.
• "Letter to Me" was Paisley's sixth consecutive #1 hit on the Hot Country songs chart and his 10th in total.
• Brad Paisley was inspired to write "Letter to Me" after his wife, actress Kimberly Williams-Paisley, was asked to contribute to an anthology titled What I Know Now: Letters to My Younger Self.
• "Letter To Me" spent four consecutive weeks at the top of the country chart, but Paisley admitted during an event at the 2018 Country Radio Seminar that he never expected it to become a single at all.
  
  "That song was written 100 percent for myself; it was never intended to be a single," he recalled. "We cut it for all the right reasons, which basically were that we knew it needed to exist."
  
  "We sit around in [Nashville] a lot and say, 'Here's a thing we could put together that the fans would want to buy,'" Paisley added. "But that's the wrong way to do it. We need to think more about what's going to get people emotional. I think that the best music is the music that you mean."