How about:

"There's a hole in Daddy's arm where all the money goes" from John Prine's 'Sam Stone'

"I played The Red River Valley, and he sat in his kitchen and cried" from Guy Clark's 'Desperadoes Waiting For A Train'

and a combination of the singer and the song in the way Gram Parson's voice breaks on the line "I'm your toy, I'm your old boy" from 'Hot Burrito#1'