After a troubled youth that saw him in and out of youth reformatories, Haggard was finally sent to Bakersfield jail for a bungled robbery and, after an escape attempt, transferred to San Quentin prison on February 21, 1958. He was released in 1960. By 1967, he was on the cusp of country stardom when he hit number one on the country singles chart with the Liz Anderson composition "I'm A Lonesome Fugitive." Understandably,

Haggard was concerned about the effect his time in prison might have on his career but, as Daniel Cooper writes in the liner notes to the 1994 box set Down Every Road, it had little effect at all: "It's unclear when or where Merle first acknowledged to the public that his prison songs were rooted in personal history, for to his credit, he doesn't seem to have made some big splash announcement.

His prison record is never mentioned in a May 1967 profile in Music City News. But in July 1968, in the same publication, it's spoken of as if it were common knowledge. Haggard would be legally pardoned for his past crimes by California's Governor Ronald Reagan in 1971.