Although Kristofferson commercial stock was high, some reviewers contended that the quality of his songwriting was slipping due to his preoccupation with Hollywood.

Rather than record with longtime producer Fred Foster in Nashville, the singer opted to record with Coolidge’s producer David Anderle at Sunset Sound in Los Angeles, and the resultant LP, sandwiched between two duet albums with wife Coolidge in 1973 and 1974, deals almost exclusively with dissipation and decline, to the point where it could be viewed as a concept album.

As William Ruhlmann observed in his AllMusic review of the LP, "Over and over, Kristofferson sang of characters and of himself (or, at any rate in the persona of a first-person narrator) going downhill while consuming liquor and drugs.

Even though the lyrics are imbued with an enigmatic wisdom, there is a sense that Kristofferson is trying too hard, failing to recreate the kind of seemingly effortless results he achieved on songs like "Me and Bobby McGee".

Beginning with Spooky Lady Sideshow, Kristofferson would blame his commercial downturn on Monument's lack of promotional support rather than his acting career, and he dismissed the notion that he ought to quit Hollywood, later quipping "I was doing movies, in a bathtub with Barbra Streisand!