Pilgrim did not regard singing as a long-term career, and said he only became a professional singer to enable him to give up his job at a bank, in order to go to university and get a degree at the London School of Economics.
He sang with the Oscar Rabin Orchestra and was featured for over 190 consecutive weeks singing live on the popular BBC radio programme Go Man Go.
"Little Christine" was a successful hit for Dick Jordan, Burt Blanca and Danny Fisher, "Just One More Dance" was recorded by Lee Curtis, and "Big Boy"—which was an English version of the Norwegian Eurovision Song Contest song "Voi Voi"—was performed and recorded by Nora Brockstedt.
Eventually, Pilgrim gave up singing after he gained his degree and made a successful career in information technology.
However, he briefly came out of "retirement" to record his last session in April 1966, singing the theme song for the film Carry On Screaming!.