You couldn't find two performers more diametrically opposed than David Bowie and Bing Crosby. Crosby was a well-known crooner who had made his career entertaining post-war fans with his smooth voice. Bowie, in contrast, was the androgynous glam rock icon whose transgressive career was about as far away from Crosby as could be.
So this legendary performance shocked both fans and contemporaries and their collaboration became a massive success. The track was recorded on September 11th, 1977 for Crosby's television special, Bing Crosby's Merrie Olde Christmas, which was to be one of Crosby's last. Bowie's appearance has been described as a "surreal" event, undertaken at a time when he was "actively trying to normalise his career." Bowie apparently hated the original version of Little Drummer Boy, so he wrote his counterpoint. Crosby and Bowie rehearsed for less than an hour before performing on the special. The song quickly became a staple of radio stations for months afterward.
Listen to this beautiful performance below.