Okay, so I have already included Bing Crosby once in this little pet project of mine. But, I mean, it's Bing Crosby! The very voice of Christmas! And this just happens to be the best-selling single of all time, holiday-themed or otherwise.
Crosby first sang the Irving Berlin–penned "White Christmas" on his NBC radio show The Kraft Music Hall on Christmas Day, 1941. It was later featured in two movies in which he starred: 1942's Holiday Inn (as a duet with Marjorie Reynolds) and 1954's White Christmas, which also included a reprise of the song including Crosby's costars Danny Kaye, Rosemary Clooney, and Vera-Ellen. (TRIVIA TIME: Vera-Ellen's vocals were actually performed by Trudy Stevens.)