The songs on the album were recorded with Taylor's band The Flying Machine in a late 1966 three-hour session in New York City's Select Sound Studios. They were produced by Chip Taylor, who had been involved in some recent pop hits, and Al Gorgoni, who also added harpsichord to the band's sound. The group felt the resulting tracks were of only demo quality. After "Brighten Your Night with My Day"/"Night Owl" was released as an unsuccessful single by Jay Gee Records, a subsidiary of Jubilee Records, no work towards an album release went forward.
Taylor subsequently signed with Apple Records, failed commercially again, but then became a huge success with Warner Bros. Records on Sweet Baby James in 1970 and Mud Slide Slim and the Blue Horizon in 1971. Euphoria Records then released the sessions using the name "The Original Flying Machine", to distinguish the group from the UK outfit The Flying Machine who had emerged in 1969 with the hit song "Smile a Little Smile for Me". The released album had modest success capitalizing on Taylor's fame, reaching #74 on the U.S. pop albums chart. Flying Machine member Danny Kortchmar was not pleased, saying "The people involved wouldn't spring for the money for a whole album of James' songs [in 1967]. So it seemed terrible years later when the same people put out the Flying Machine album of those few sessions."
The sessions album was re-released by Gadfly Records, with some additional songs, in 1996.