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.