Honorable Mentions
Serendipity has almost nothing to do with Christmas, but it does start and end at Christmas time. Jonathan and Sara meet while shopping for a pair of gloves. They just happen to be looking for the exact same pair. He's looking to buy them for his girl friend for Christmas and she wants them for herself. They connect but they are both in relationships. When Jonathan pushes Sara for her number, she makes a deal with him. She writes her number in a copy of the book she's reading and he writes his on a five-dollar bill.
Several years later just before his wedding, Jonathan decides he needs to try to find Sara to convince himself that he didn't miss out on something important. Sara meanwhile has just gotten engaged to her musician boyfriend and looks for Jonathan for the same reason. I'll stop there. You should see this for yourself.
Holiday Inn starts with Jim (Crosby) deciding to get out of show business after his partners Ted (Astaire) and Lila are leaving the act to get married. Jim has the crazy idea of buying a farm and living the easy life. After trying the easy life he gets another crazy idea. He decides to that the farm house and turn it into a club that is only open for holidays. He figures he can make enough on the holidays to live the easy life.
While getting things around on Christmas Eve for the opening night on New Year's Eve, Jim meets Linda an aspiring dancer and singer who is hoping to work for at the Inn. There's an immediate connection and he teaches her "White Christmas" one of the songs for the following year.
Things get interesting when Lila leaves Ted for a millionaire and Ted decides Linda is the perfect choice for a new partner. This movie is great for every holiday of the year.
In "Going My Way," Crosby plays Father O'Malley a young priest who has been sent to help out at a struggling parish. While helping Father Fitzgibbon, the older priest, figure out what the parish needs, he also manages to help out a struggling singer, turns the local ruffians into a choir, and make life in the parish a better place all the way around.
I won't say much more about this movie and its connections to Christmas since that will ruin the ending, but it is a fun movie. Also if you look closely you can spot the boy who played Alfalfa in the "Little Rascals as one of the boys in the choir.
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