Jon Randall, one of the song's co-writers, had just divorced from country singer Lorrie Morgan before writing this song. In addition, he had lost a record deal, and had not been able to find a songwriting contract either. He found himself drinking whiskey regularly, and pursuing sexual desires. After seeing the condition that Randall was in at the time, his manager told him, "Hey man, every now and then you've got to put a bottle to your head and pull the trigger." 
Randall then wrote down that line, and decided to use it in a song. He then met Bill Anderson and began to write the song, which eventually made its way to Paisley. Randall himself also included a version on his 2005 album Walking Among the Living.

Lyrics

(Brad)
She put him out like the burnin' end of a midnight cigarette
She broke his heart, he spent his whole life tryin' to forget
We watched him drink his pain away a little at a time
But he never could get drunk enough to get her off his mind,
Until the night.

Chorus: (Both)
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.


(Alison)
The rumors flew but nobody knew how much she blamed herself
For years and years she tried to hide the whiskey on her breath
She finally drank her pain away a little at a time
But she never could get drunk enough to get him off her mind,
Until the night.

Chorus: (Both)
She put that bottle to her head and pulled the trigger
And finally drank away his memory
Life is short but this time it was bigger
Than the strength she had to get up off her knees
We found her with her face down in the pillow
Clinging to his picture for dear life
We laid her next to him beneath the willow
While the angels sang a whiskey lullaby.


Whiskey Lullaby [Brad Paisley Feat. Alison Krauss]

Quintessential tortured young soul, too intellectually mobilized for my age (or so i think). Gaston Bachelard, Edmond Jabes, Sylvia Plath, Rainer Maria Rilke, Charles Baudelaire, Octavio Paz, Saul Williams, Charles Bukowski, and Daniel Albright are my salvation and recourse. I go back to them on days both dark n' bright. 
*the tale of a bath tub*

Whiskey Lullaby [Brad Paisley Feat. Alison Krauss]

NB.