Until this album, Chet Baker was primarily an instrumentalist. His mother had encouraged him to sing for years, leading him to record two tracks in October 1953: "I Fall in Love Too Easily" and "The Thrill is Gone." He then requested to record a full album of his singing, which met skepticism from his producer, Dick Bock.

The album was recorded in Hollywood, with Russ Freeman selecting several songs for Baker. According to James Gavin, Bock was alarmed by Baker's struggle to sing in key, requiring numerous takes for each song. Despite this, Baker persisted, frustrating the background musicians. Freeman later remarked, "I thought it was bullshit. Louis Armstrong and Jack Teagarden sang like jazz singers. This was ballads. Totally meaningless."