Miracle on 34th Street: I remember the first time I went to New York, I took a photo of the 34th street sign outside Macy's. I don't actually love the old version, but I do like the more recent (mid-90s maybe?) version with hottie Dylan McDermott. And Sir Richard Attenborough does play the sweetest Santa.
Mr. Magoo's Christmas Carol: If you ever want to be scared out of your mind as a child, check out the Ghost of Christmas Future in this movie. Terrifying! But, there are some good tunes in this one, including a whole song about razzleberry dressing, and a heartbreaking one about Scrooge not having a family. It includes the line "A hand for each hand was planned for the world, why don't my fingers reach?" Geez, on retrospect, Mr. Magoo, you're depressing.
A Christmas Story: This really needs no description, but this movie taught me a lot about living in cold weather, as well as why you lock your back door when cooking a turkey. And while I've gotten some questionable gifts, none have been as terrible as the bunny pajamas . . .
Meet Me in St. Louis: I first watched this movie at my grandmother's when I was in elementary school. I watched it so much at her house that she bought me my own copy. Could be questionable as a Christmas movie as it follows the four seasons in the life of the Smith family. Judy Garland plays the main Smith child, Esther, but really the whole family is enchanting. They live in St. Louis at the turn of the 20th century, right before the World's Fair opens (the what? Yeah, wikipedia it, used to be a big deal). The simpler times (washing your hair was a big venture for the evening), family dynamics (sisters scheme to invite the cute boy next door to their brother's party), and songs (The Trolley Song, Have Yourself a Merry Little Christmas) make this movie one of my favorites of all time.
Senior year of college, I took a class with friends all about musicals (literally, it was called The Musical). It was a night class held once a week, so we'd take notes for an hour and then watch a movie for the rest. This was one of the movies we watched in class, and I was giddy about it for weeks. To the point that one of my friends asked another friend taking the class "Has Lo told you that Meet Me in St. Louis is one of her favorite movies? Because she's told me several times." One thing I learned about this movie from that class is that it was released at a time when movies about simpler times were very popular. World War II had just ended and the country wanted to be reminded of a time when life was easy (like 40 years earlier). There was also an overwhelming feeling of Americana (due to winning WWII) and movie studios capitalized on that by making films that promoted American pride and showed how great our country is.
Ok, lesson over. Watch Meet Me in St. Louis (and let me know your favorite part!)