Most people are familiar with How the Grinch Stole Christmas, but if you haven't shared this classic with your kids read it first (because you should always read the book first) and then watch the animated version. I do not recommend watching the live action film, especially with little kids. Don't get me wrong, Jim Carrey is a comedic genius, but his portrayal of the Grinch is just creepy. Actually the whole movie is creepy and so is the live action Cat in the Hat. The weirdly wonderful imagination of Dr. Seuss really only works with animation at least in my opinion).
Speaking of classic Christmas stories that I love to reread every year, Cranberry Christmas is one of my favorites. Does anyone else remember the Cranberry series by Harry and Wende Devlin? The first book, Cranberry Thanksgiving, was published in 1971 and it was followed by a slew of other books featuring Maggie, Grandmother, and Mr. Whiskers in the town of Cranberryport. Cranberry Christmas came out in 1984 and I must have read it a few hundred times. I adored Mr. Whiskers and I even tried cranberries for the first time because of this book.
I am probably the only that remembers this one too, but I don't care. It is still one of the all time greatest Christmas stories ever written and subsequently turned into a movie featuring Jim Henson's Muppets. Have you guessed or is the suspense killing you? It's Emmet Otter's Jug Band Christmas!!! Russell and Lillian Hoban are probably best known for the adorable Frances Series, but in my opinion, Emmet Otter is their greatest collaboration. Believe it or not (and no doubt you will if you know me because I then you know how weird I am) I still have my Weekly Reader edition of this book. Yes, I got Weekly Reader books as a kid!
The book was first published in 1971 and Jim Henson (one of my idols) directed the television special in 1977. Words cannot express how much I love Emmet Otter's Jug-Band Christmas, both the book and the muppet version. I used to have Emmet Otter's Jug-Band Christmas on VHS, but (HOORAY) now I have it on DVD! The last few years my daughter (who is now 13) has given me the eye roll and snotty "Do we have to watch this again?" I still make all three of my kids watch Emmet Otter with me, though. It's a Christmas tradition (whether they want it to be or not-Mwaahhaaahaaa!).
Another childhood favorite is The Best Christmas Pageant Ever by Barbara Robinson. Who could ever forget the Herdmans who terrorize the neighborhood, but ultimately teach the community the true meaning of Christmas after they take over the annual church Christmas Pageant. I have read this a couple of times to my kids and we have also watched the made for television movie starring Loretta Swift (from MASH). A couple of years ago Harper Collins came out with a picture book version of The Best Christmas Pageant Ever, but the original 1971 chapter book is still the best.
I am not even sure if it qualifies as a Christmas book, but The Velveteen Rabbit always puts me in a Christmasy state of mind. After all, when we are first introduced to the toy rabbit he is in a little boy's Christmas stocking.
I would describe William's beautiful, heartstrings-tugging book as the original Toy Story.
If you visit the Steam Railroading Institute in Owosso, Michigan you can ride the real Polar Express, the Pere Marquette 1225. The 1225 provided the sound effects and was used as the model for the film The Polar Express. You can purchase tickets to ride the 1225 year round, but every winter the Polar Express travels to the North Pole where kids can meet Santa, and enjoy rides, games, and other Christmas activities.
Once your kids are older it is time to introduce them to classic holiday films. Personally, I only watch the original movies and certain ones have to be in black and white. For some reason Holiday Inn, Miracle on 34th Street, and It's a Wonderful Life are just not as good in color. Now, White Christmas was filmed in color so that one is okay.