This Ole Boy is Morgan's first release for the independent Black River Entertainment. He told Billboard that he "felt like they had more going on, and more potential as an independent than anybody out there", and compared the label to Broken Bow Records, for which he recorded from 2002 to 2007.
The first single from the album is its title track, written by Rhett Akins, Dallas Davidson and Ben Hayslip, also known as the Peach Pickers. The song was previously recorded by Joe Nichols on his 2011 album It's All Good. Morgan co-wrote seven songs on the album and co-produced it with Phil O'Donnell. Morgan co-wrote with Shane Minor and Jeffrey Steele, two of the writers of his 2007 single "International Harvester", on "Corn Star", which was released as the album's second single, and ultimately peaked after five weeks at #50 on the country chart. The album's third single, "More Trucks Than Cars", debuted at #56 on the country chart for the week of September 15, 2012.
The album's release was preceded on November 1, 2011 by a digital-exclusive extended play also titled This Ole Boy, which comprises the title track, "The World Needs a Kitchen", "Fish Weren't Bitin'", "Show Me Your Tattoo" and "Better Stories".
Giving it three-and-a-half stars out of five, Country Weekly reviewer Jessica Nicholson said that his "standard good-ole-boy fare[…]finds Craig at his most confident and comfortable." An identical rating came from Matt Bjorke of Roughstock, who said that "Craig Morgan has certainly returned with a strong album worthy of becoming a collection of big hits."