"Stupid Cupid" is a song written by Howard Greenfield and Neil Sedaka which became a hit for Connie Francis in 1958. In the spring of 1958 Francis had hit #4 with her breakout hit, a rock ballad version of the standard "Who's Sorry Now?". The similarly-styled follow-up "I'm Sorry I Made You Cry" had barely reached the Top 40 and Francis recalls: "I knew I had to come up with a hit on the third record. It was crucial.
Francis cut "Stupid Cupid" on 18 June 1958 at Metropolitan Studio (NYC); LeRoy Holmes conducted the orchestra while Morty Kraft produced the session. Noteworthy in the recording is the uncredited bass guitar work; a complex and energetic riff that has survived the decades and has proven to be one of early rock and roll's best recorded bass guitar sessions. A version of "Carolina Moon" recorded at Metropolitan Studio that 9 June with Kraft producing and Joe Lipman conducting was utilized as the B-side. "Stupid Cupid" provided a reasonably strong comeback vehicle for Francis reaching the Top 15 that August with a Billboard Hot 100 peak of #14.