From being a writer for hire in the 1950s to his solo pop stardom and emphatic 1970s comeback, the late musician’s catalogue is stuffed with stunning, surprising songcraft

News: Neil Sedaka, Breaking Up Is Hard to Do singer and pop song hitmaker, dies aged 86

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.

Sedaka got his breakthrough as a performer with 1958’s The Diary – inspired when Connie Francis refused to let him and songwriting partner Howard Greenfield scour her diary for inspiration. Oh! Carol, meanwhile, was a paean to Sedaka’s ex-girlfriend Carol Klein – the irrepressibility of the melody at odds with the misery in the lyrics (“I am but a fool!”). Klein was impressed enough to write an answer song, Oh! Neil, which she recorded under her new pen name: Carole King.