Deemed "one of pop music's most curious couplings" by USA Today[3] – the tour involving the cross-genre, cross-generational pairing came about as a consequence of Clarkson's career battles surrounding the release of her 2007 album, My December.

[3] The two teamed up together for McEntire's Reba: Duets album, released in September 2007, as well as on the television program CMT Crossroads,[5] in the process, discovering "a spark between the two" of them.

[5] It was rumored in October 2007, by one of McEntire's band members that the two singers would tour together and the first date was confirmed on November 14, 2007 by West Virginia station WTRF-TV.

The first leg of the tour proved to be an overwhelming success, selling out all fifteen shows[7] and grossing over US$7 million, and performing to over 400,000 people.

The critic went on to state: "McEntire exhibited a honed mastery of the material – be it Clarkson's or her own – and a professional command of the stage.