"Jingle Bells," copyrighted in 1857 by James Pierpont (uncle of J.P. Morgan), was originally not a holiday song at all. It was written for a Thanksgiving church service, as legend has it, and was so popular, it was performed again at Christmas.
Several well-known tunes emerged from films of the 1940s and '50s. Irving Berlin's "White Christmas," sung by Bing Crosby in the 1942 "Holiday Inn," has become the most recorded holiday song to date, with more than 500 versions.
The "Singing Cowboy" Gene Autry initially balked at recording "Rudolph the Red-Nosed Reindeer," thinking it didn't fit his image. His wife convinced him otherwise, and the 1949 song became his biggest seller.