In May 1940, Irving Berlin signed a contract to write songs for a film musical based on his idea of an Inn that opened only on public holidays. "White Christmas" was originally written by Irving Berlin for a 1942 movie "Holiday Inn". Berlin's assignment was to write a song about each of the major holidays of the year. He found that writing a song about Christmas was the most challenging. When Bing first heard Berlin audition "White Christmas" in 1941, he reassured Irving that he had created a winner.
Bing Crosby and Fred Astaire were the stars of Holiday Inn with support from Marjorie Reynolds and Virginia Dale. Produced and directed by Mark Sandrich, filming took place between November 1941 and February 1942. Holiday Inn had its premiere at the Paramount, New York in August 1942. It was a runaway success both in America and in England, proving to be the top grossing musical ever up to that time. The big song had been expected to be 'Be Careful, It's My Heart' and while it did very well, it was White Christmas which topped the charts in October 1942 and stayed there for 11 weeks.
Cosby and Astaire teamed up again in 1946 in the movie "Blue Skies" which was another vehicle for Irving Berlin's Songs. The success of the song "White Christmas" led eventually to a movie based on the song.