3. Meet Me In St. Louis
This enchanting 1944 Judy Garland-starring musical actually only has a few Christmas-set scenes and follows the four Smith sisters in the year leading up to the 1904 St. Louis World's Fair. But it brought us the somehow impossibly sad classic song "Have Yourself a Merry Little Christmas" (google the original lyrics and you'll want to take an icicle to the heart) sung beautifully and bittersweetly in one highly iconic scene by Garland to a young Margaret O'Brien.