No performer of the 20th century was more associated with Christmas than Bing Crosby. From 1931 until 1962, he was the star vocalist of radio. His popular Chesterfield Show, sponsored by the cigarette company, aired on Wednesday nights from 1949 through 1952. Read more about Bing’s radio career here, and enjoy this Chesterfield holiday show, with guest star Al Jolson, which was originally broadcast on 12/28/1949. Were you listening then?