Brothers Osborne, Lucie Silvas, Brent Cobb, Anderson East, Margo Price and Marty Stuart joined Stapleton as special guests playing selected dates.

"[7] Chuck Yarborough for The Plain Dealer opined Stapleton "actually sings like the love child of Marvin Gaye, Joe Cocker and the Hag.

Tulsa World journalist Andrea Eger, who attended Stapleton's first concert since he had to reschedule dates due to a hand injury, expressed, "there were absolutely no signs he wasn’t 100 percent–and he's one of those singers for whom recording simply does too little justice to the quality of his live vocals,"[9] while Cleveland Scene's Laura Morrison, who attended a different date, wrote, "his wizened and chest-aching vocals howled to the moon last night just as righteously as they do on his albums.

"[13] Kevin Coffey of Omaha World-Herald shared a similar sentiment, saying, "Stapleton played lead and rhythm on every tune, and he did it very well, even busting out some bluesy solos that went on and on.

"[15] For Dallas Observer, Holly Lafon wrote, "Stapleton's show was refreshingly free of the overglamorized accoutrement of country's current biggest pop stars.

A low-key performer by nature, he kept the focus on the playing [...] The range of his repertoire stretched from stone country to hard rock with plenty of soulful blues in between [...] When he let his guitar do the talking–playing a succession of vintage instruments that had any aficionado drooling–Stapleton was a force to be reckoned with, searing and shredding on songs such as "Death Row", "Second To Know" and extended versions of "The Devil Named Music", "Outlaw State Of Mind" and the show-closing "Sometimes I Cry.