Crosby first sang Irving Berlin’s beloved holiday classic on his NBC radio show The Kraft Music Hall on Christmas day in 1941, and again in 1942 as part of the soundtrack to the film Holiday Inn. The wistful holiday classic resonated especially strongly with many Americans when it was first released in 1941, just 18 days following the attack on Pearl Harbor. “By the following winter, young American troops found themselves overseas during the holidays,” says Seattle’s KUOW. “Armed Forces radio played ‘White Christmas’ over and over to remind them of home.” The warmly nostalgic song was always the No. 1 request when Crosby went overseas to perform for the troops, even though Crosby had doubts about performing it, says KUOW. “I hesitated about doing it because it caused such a nostalgic yearning among the men, that it made them sad,” Crosby once recalled. “Heaven knows, I didn’t come that far to make them sad. For this reason, several times I tried to cut it out of the show, but these guys just hollered for it.” Though Crosby’s 1940s recordings of “White Christmas” are perhaps the best known, the singer’s duet with Frank Sinatra is also definitely worth a watch. The pair performed this casual duet in 1957 on The Frank Sinatra Show, and they seem to enjoy sharing a cozy holiday moment, sipping eggnog before sitting down to a full Christmas dinner. Watch Bing Crosby and Frank Sinatra perform “White Christmas”: Next: The Best Christmas Movies Ever
