For those who have heard “Whiskey Lullaby,” you know it’s a truly heartbreaking and tragic song about betrayal, regret, and self-blame. 

And the moment Brad Paisley heard the song; he knew he had to rec ord it. He enlisted another country superstar for a breathtaking duet – and it’s none other than the female artist with the most Grammy wins, Alison Krauss.

Released in 2004 off Paisley’s album Mud on the Tires, “Whiskey Lullaby” peaked at No. 3 on Billboard Hot Country Singles and Tracks charts and was even a crossover success reaching No. 41 on the Billboard Hot 100. 

The song also won the 2005 Country Music Association Song of the Year Award.

“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,” Paisley said about the song in 2013 with Entertainment Weekly.

“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 my 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.”

A Song Written By Legends

Written by Bill Anderson and Jon Randall, “Whiskey Lullaby” tells the tale of a couple who had an abruptly painful separation leading both to alcoholism. In what seems to be an unfortunate event, the two eventually found themselves drinking to death: first, the man, with a broken heart, and followed by the woman, feeling guilty for the man’s death.

“He put that bottle to his head. And pulled the trigger and finally drank away her memory. Life is short, but this time it was bigger than the strength he had to get up off his knees. We found him with his face down in the pillow with a note that said, “I’ll love her ’til I die.” And when we buried him beneath the willow, the Angels sang a whiskey lullaby,” the song goes.

Anderson told The Boot the story behind the song. He recalled how Jon Randall was going through such a difficult time before writing the song. He had gotten a divorce from country star Lorrie Morgan. And just when Randall thought things could not have gotten worse, he lost his writing deal and record deal all within just a day or two of each other. 

Randall found himself drinking whiskey regularly and had been sleeping on a friend’s couch for the last couple of weeks. Until one day, he finally decided to sober up, come back, and join the living again. It was then he realized, “I’ve been an inconvenience to you. I’ve been an intruder, really, in your life and your home”, to which his friend answered, “That’s all right, Jon. I’ve put the bottle to my head and pulled the trigger a few times myself.” So, when Randall came to the writing session, that was fresh on his mind.

Anderson has also recounted to author Jake Brown in Brown’s 2014 book, Nashville Songwriter, how the song was supposed to be called “Midnight Cigarette.”

“Can you imagine a cigarette just sitting on an ashtray at midnight? Nobody’s smoking it or paying it any attention, and it just sort of burns out and goes out all by itself, and liken that to a relationship – it wasn’t like you hit a wall or anything, it just burned out, it just went away,” Anderson said.

Randall loved the idea, so they started combining lines, and the song turned out to be one great example of cowriting in its purest form. Anderson and Randall managed to contribute pretty much equally to the process.

Tune in below and enjoy Brad Paisley and Alison Krauss’ deeply chilling and emotional performance of “Whiskey Lullaby” in the video below.