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20 Vintage Holiday Movies That Will Never Go Out Of Style

7. Holiday Inn

Bing Crosby's successful precursor to White Christmas, this 1942 musical finds him teaming up and facing off with Fred Astaire as his frenemy. The plot basically involves hi-jinx surrounding a love triangle at Crosby's farm turned musical theater that opens only for public holidays (So Christmas, yes, but also ... Lincoln's birthday, which, warning: includes an actual blackface number) but the film is really just a showcase for Irving Berlin's iconic songs, including "White Christmas" and "Easter Parade," which both went on to inspire their own holiday films.