The song is a mid-tempo country ballad, mostly accompanied by acoustic guitar and saxophone.

It was written as a tribute to basketball player and jazz musician Wayman Tisdale, who died on May 15, 2009.

Ken Tucker of Billboard magazine said that "Dave Koz's saxophone is a perfect accompaniment to the tender and touching 'Cryin' for Me (Wayman's Song)',"[3] and Entertainment Weekly writer Whitney Pastorek called it a "sweet tribute to a friend who passed away.

"[4] Bobby Peacock of Roughstock called it "one of the best single releases of Toby's career" and compared its theme to Alan Jackson's "Sissy's Song," "but with a few more personal touches.

"[7] The music video, directed by Michael Salomon, premiered on CMT on November 2, 2009.