Connie Francis – Stupid Cupid (1958)
As a young jobbing songwriter charged with devising a hit for Connie Francis after the singer released a couple of flops, Neil Sedaka was unsure about Stupid Cupid: modest to a fault, he suggested that Francis, “a classy lady”, would be insulted by its daftness. Instead, she literally jumped up and down with excitement when she heard it. Understandably so: if Stupid Cupid is certainly silly – listen to the off-key guitar twangs – it’s irresistibly silly, a perfect encapsulation of a certain kind of 50s pop innocence, and Francis’s vocal completely sells it.