The tracklisting includes fan favorites, the No. 1 single “This Is The Night,” the Top 5 “Solitaire” and others handpicked by Aiken from his albums. The album was released on March 31, 2009. A PDF file included on the CD contains the song credits, photographs, and liner notes.
First week sales of 3,000 copies placed Playlist: The Very Best of Clay Aiken at number 173 on the Billboard 200 chart and at number ten on the Top Internet Albums chart.
"The Way"/"Solitaire" was released as a commercial single on March 16, 2004. "The Way" peaked at number one on the Canadian Singles Chart. In the summer of 2004, a second version of the Measure of a Man album was released in which "Solitaire" replaced "This is the Night" as a bonus cut. "The Way" music video was directed by Diane Martel. Instead of the traditional Hollywood types Aiken hired everyday people to play the couples shown in this video.
"The Real Me" was originally recorded by Natalie Grant for her album Awaken (2005). Aiken stated in an interview that Grant rewrote some of the lyrics for him.
"Something About Us" was written and recorded by Michael O'Brien for his album Something About Us (2007).