Start with How the Grinch Stole Christmas and as his two-sizes-too-small heart begins to fill with glad tidings so will you. Featuring the classic song "You're a Mean One, Mr. Grinch" and all those cute little Whos down in Whoville, Dr. Seuss' Christmas masterpiece is still irresistible after all these years.
Next, try the wonderfully gloomy The Nightmare Before Christmas. The king of creepiness, Tim Burton, put a new twist on holiday-themed movies with this artfully-told tale. It seems that Jack, The Pumpkin King, is tired of celebrating Halloween and decides to give Christmas a try instead. But can a lonely little skeleton find acceptance (and maybe even romance) in snowman's land? You'll just have to watch and see.
Travelling farther back in time, the 1970 TV special Santa Claus is Coming to Town, by Arthur Rankin, Jr. and Jules Bass (the same duo responsible for Rudolph the Red-Nosed Reindeer and Frosty the Snowman among others), tells the story of Santa from the time he's left as a baby on the doorstep of the toy-hating Burgermeister Meisterburger. Fortunately, he's rescued by the Kringle elves (Wingle, Dingle, Tingle, Bingle, Kingle and Tante) who raise him and teach him their trade: toymaking. Once he's old enough, Kris Kringle faces down the Winter Warlock to bring toys to the kids of Sombertown. Rankin and Bass's trademark stop-action animation give the story it's charm, and as an added bonus you'll learn Santa secrets like why he wears a red suit, how he knows if you're naughty or nice, and how the reindeer learned to fly. Also, you'll get to see Mrs. Claus back when she was a hottie (who knew?).
In another Rankin/Bass creation, The Year Without a Santa Claus, you hear the story of "the furious, curious, fridigy year when Santa unhitched his sleigh and vowed he was taking a holiday." Okay, so maybe they take the rhyming thing too far in this one, but all the great characters and kitschy songs more than make up for it. You'll meet elves Jingle and Jangle Bells as well as the villainous Snow Miser and Heat Miser. Of course, the big question is does Santa come around in time and deliver the goods? I won't ruin the ending for you, but I will tell you this: It's a general rule of holiday movies to always end happily. That's all I'm going to say.
A Charlie Brown Christmas is possibly the most serious of the fun holiday shows. Like a lot of people at this time of year, Charlie Brown isn't feeling very festive so to get into the spirit of the season he decides to direct the gang's Christmas play. Highlights include the sad little tree Chuck chooses being transformed by love--and Linus' blanket--and a reading of the biblical account of Christ's birth from the book of Luke. After all, when was the last time you saw a cartoon that featured a Bible reading that wasn't totally cheesy and on some religion channel?