Despite a string of #1 albums and sellout concerts, the overhead of keeping his show on the road combined with his cocaine habit had drained nearly all of his resources.

In the audio version of his autobiography Waylon, he admitted to spending up to $1,500 a day on the drug and also confessed to being out of touch with the personnel on his tours: In the spring of 1981, Jennings, drummer Richie Albright, and financial advisor Bill Robinson went over the singer's business affairs at a hotel in Los Angeles and found that he owed more than two million dollars and was over $800,000 overdrawn to the bank.

[1] Jennings slowly crawled out of debt by trimming down his organization and touring heavily, including a lucrative engagement in Las Vegas.

Perhaps the album's most moving performance is Jennings' rendition of "Song for the Life," originally recorded by Rodney Crowell, who also composed the tune.

Instead, the album closes with the Bobby Emmons' brazen "Get Naked With Me," which Jurek deems "a stupid song in the old, tired outlaw frame."