Doug Freeman of the Austin Chronicle credits Crowell for "balancing ballads and bar room stomps ... with his characteristic sense of autobiographical detail and precarious mortality.

[10] Steve Johnson of the Chicago Tribune rated the album three-and-a-half stars out of four, writing that "With effortless melodies played with the grace and unforced power from a veteran band, 'Tarpaper Sky' showcases Crowell's still-potent voice, all honey and cedar and sly inflection, and his knack for finding the words to make simple wisdom and an older man's reflections resonate.

"[8] Luke Torn of Uncut rated the album an eight out of a ten, writing how "Crowell’s versatile, impassioned voice is in fine fettle, a confident mix of goofiness and longing, anticipation and excitement, sadness and sentimentality, as if he’s just now entering a new prime.

"[9] At The Austin Chronicle, Doug Freeman rated the album three-and-a-half stars out of five, writing how the release "proves that the Houston Kid in his 60s remains as vital as ever, balancing ballads and bar room stomps, both cut with his characteristic sense of autobiographical detail and precarious mortality.

"[11] At Blurt, Lee Zimmerman rated the album four stars out of five, stating that "Tarpaper Sky finds Crowell yet again emphasizing the superior songwriting skills that have been his stock in trade since the very beginning.