On the Sentimental Side was intended to be a long-playing vinyl album and it was recorded in June 1962 by Bing Crosby for his own company, Project Records at United Recording, Hollywood. The album is in a “sing-along” style and Crosby over-dubbed his vocals on accompaniment recorded by the Ivor Raymonde Orchestra and chorus in London in March 1962. The original sessions were produced by Simon Rady for Project Records.