During an interview included in Nashville Songwriter: The Inside Stories Behind Country Music's Greatest Hits
by Jake Brown, Anderson said that he and Jon Randall wrote the tune back in 2000 as something to be sung by one person. However, he added, "people weren't lined up down the street looking for double-suicide drinking songs, so it sat on the shelf for five years."
Dixie Chicks were the first act to have the song on hold had but their career imploded in the meantime. Then Brad Paisley heard the tune and spotted its potential as a duet. Anderson recalled: "Brad called me one day on the phone, and said, 'I've been listening to this "Whiskey Lullaby," what would you think if I brought a girl to sing on that second verse?" And I said, 'I've never thought of that. Who do you have in mind?' And he said, 'Well, I think there's only two people who could do it, and I would like to have one of those: Alison Krauss or Dolly Parton.' And I told him, 'Well, you don't have to ask my permission to do that, because I love them both!' So next thing I knew, they worked out all the contract stuff with Alison and everything fell into place."