Following on the success of the single "This Diamond Ring" and their debut album of the same name, Lewis and the band went back into the studio with producer Snuff Garrett and arranger Leon Russell and recorded their second album, A Session with Gary Lewis and the Playboys, which was released fin August 1965. While the album did have several original songs, it, like their debut, mainly relied on covers of recent popular songs by artists as diverse as The Yardbirds, Ricky Nelson, The Everly Brothers, and Freddy Cannon. Riding on this success, Lewis would release his third charting album, Everybody Loves a Clown only three months later.