In the Nineties, Yoakam had been a musician who dabbled in movies, but by 2000 he was absorbed in a film project of his own called South of Heaven - West of Hell.

Yoakam and producer-guitarist Pete Anderson had helped revitalize the genre of country music in the late Eighties and early Nineties, scoring a triple platinum high point with This Time in 1993.

However, with the release of Gone in 1995, Yoakam's commercial stock took a nosedive, and his growing preoccupation with acting left Anderson perplexed, with the producer later reflecting in 2003: Dwight has, still has and has had the potential to be, you know, the most important country artist of his time.

And that’s my personal opinion, and why he would leave, or descend from, or not maintain a mantle of that structure to become a - um, no, I barely, I don’t know what kind of – a character actor?

[5]While Yoakam nursed his acting bug, country radio's youth-obsessed fixation continued and the singer developed a strained relationship with his label Reprise.

In his AllMusic review of the album Hal Horowitz writes: Yoakam goes the Hank Williams Sr. route on "A Promise You Can't Keep" and especially "The Heartaches Are Free," which sounds so similar to a Hank Sr. tune in melody and vocal inflection, you'll find yourself double checking the liner notes to be sure it's a Yoakam original…song titles like "A World of Blue," "A Place to Cry," "The Sad Side of Town," and "Time Spent Missing You" show that Yoakam is still drenched in the spilt tears, heartbroken brand of country that has proven to be so lucrative, artistically and commercially, in the past.