Songfacts®:

• "Whiskey Lullaby" is a very sad song about a man who gets his heart broken so bad, he drinks himself to death - it's the musical equivalent of Leaving Las Vegas. His ex blames herself for his death and also starts drinking, eventually killing herself with the whiskey as well. The key line in the song is "He put that bottle to his head and pulled the trigger," a striking metaphor for what happens when drinking away one's sorrows will no longer work, and it becomes a method of suicide.
  
  The song is a duet with Alison Krauss, who sings the second verse in the role of the woman and also plays viola on the track.
• "Whiskey Lullaby," released in 2003 as part of his third album, Mud On The Tires, is Brad Paisley's most famous song, but it's not typical of his work, which is much more upbeat. He'll often perform the song in concert, but his shows are feel-good affairs loaded with funs songs like "Ticks" and "I'm Gonna Miss Her (The Fishin' Song)."
  
  In 2005 Paisley released another drinking song with a very different approach: "Alcohol," a singalong tune written from the perspective of the drink.
• "Whiskey Lullaby" earned the 2005 CMA for Song Of The Year and also took Video Of The Year at both the CMAs and ACMs.
  
  It was not, however, a #1 Country hit, probably because it didn't get all that much radio play - it's not the kind of song you want to hear over and over throughout the day.
• The song was written by Music Row mainstays Bill Anderson and Jon Randall, and was inspired by a difficult time Randall was going through, including a divorce from country star Lorrie Morgan. Anderson told AOL's The Boot the story behind the song:
  
  "Jon Randall and I wrote the song together. Jon was going through some pretty rough times back then. He had gotten a divorce and lost his writing deal and his record deal all within just a day or two of each other. And he went over to a friend's house and crashed for a couple of weeks. When he decided to sober up and come back and join the living again, he apologized to his friend. He said, 'Man, I'm sorry for the way I've acted the last couple of weeks.' And his friend said to him, 'That's alright Jon, I've put the bottle to my head and pulled the trigger a few times in my life.' So when Jon came to the writing session, that was fresh on his mind."
  
  "I went to the writing session with the idea to write a song called 'Midnight Cigarette.' Basically that turned out to be the first line of 'Whiskey Lullaby': 'She put him out like the burnin' end of a midnight cigarette.'
  
  That was what I wanted to write the whole song about. Jon loved that line so we wrote it down and then he said, 'Here's a line here: 'He put that bottle to his head and pulled the trigger.''
  
  I said, 'Well, let's forget about the 'Midnight Cigarette.' Man, you've got the perfect idea for the song there.' And it just kind of flowed from there."
• Paisley talked about the song in 2013 with Entertainment Weekly: "It's an angelic, ghostly bluegrass ballad, really a tragedy, and I think when I get to heaven, if the angels don't sound like Alison Krauss, we have been cheated.
  
  What's interesting is it was never expected to be a single. And it's a good example of how I was slowly able to expand by comfort zone, like getting away with 'I'm Gonna Miss Her' and 'Celebrity' - songs that were just not what you would have expected from the guy that did Who Needs Pictures."
• "Whiskey Lullaby" wasn't written as a duet, and it almost didn't make it off the shelf. During an interview included in Nashville Songwriter: The Inside Stories Behind Country Music's Greatest Hits by Jake Brown, Bill Anderson said that he and Jon Randall wrote the tune back in 2000 as something to be sung by one person, but "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 put the song on hold, but they didn't record it. 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."
• Musically, "Whiskey Lullaby" is an acoustic song that hews to Alison Krauss' sound than Paisley's, and the musicians on the track are mostly guys she's collaborated with, including Justin Williamson on fiddle and Jerry Douglas on Dobro. Dan Tyminski, a longtime guitarist in her backing band, Union Station, is on background vocals.
• The music video fleshes out a story about a soldier who returns home from World War II to find his wife in bed with another man. It stars Ricky Schroder of Silver Spoons and NYPD Blue fame, along with Marisa Petroro. Schroder also directed it.
  
  The video starts with a long sequence of dialogue before the music kicks in. Then the action synchs with the song as we see the pair spiral downward to their deaths, where they're buried next to each other. Surprisingly, it has a happy ending: In the afterlife they're reunited as soulmates.
• Alison Krauss was big in the world of bluegrass when this song was released in 2003 and already had a successful country collaboration under her belt with "High Lonesome Sound," a duet with Vince Gill from 1996. In 2007 she teamed up with Robert Plant for the Grammy-guzzling album Raising Sand.
• Paisley and Krauss have performed the song together from time to time, including at the Academy of Country Music Awards in 2004 and at the Grand Ole Opry's 100th anniversary celebration in 2025. In 2024, Paisley sang it at the Opry with Lainey Wilson.