Recording with Glenn Gould's piano at studio sessions on February 6 and 9, and May 20, 1963, Bill Evans used the method of overdubbing three different yet corresponding piano tracks for each of the songs on Conversations With Myself.
The album features mostly traditional standards, with the exception of two compositions by Thelonious Monk, and one Evans original, "N.Y.C.'s No Lark" (which pays homage to Evans' friend and fellow jazz pianist Sonny Clark, who had died one month before Evans began working on this album). Conversations With Myself received a 5-star review in Down Beat in 1963 and earned Bill Evans his first Grammy Award for Best Jazz Instrumental Album, Individual or Group the following year.