These films aren't in any particular order, but they are all films I watch around Christmas time to help me get into the Christmas mood.
Rudolph, the Red-Nosed Reindeer (1964)- A reindeer born with a red nose is bullied as he grows up. He and an elf who wants to be a dentist decide to leave and find other misfits like them and they find the island of misfit toys. When Rudolf finds out that his girlfriend and his family are in trouble, they go back to save them.
http://www.youtube.com/watch?v=W6IAY9bSP7s
Rudolph the Red-Nosed Reindeer (1948)- A Fleischer cartoon. Rudolph is made fun of by the other reindeer until one Christmas night when the fog is too thick and Santa can't fly out to deliver presents and only Rudolph's nose can provide enough light for Santa to see.
http://www.youtube.com/watch?v=22ZYhvOK0bI
Santa Claus is Coming to Town (1970)- This is the story of how Santa Claus came to be. He was actually an orphan who was dropped off on the doorstep of some toy making little people called the Kringles who name him Kris. As he grew up he learned various things from the animals, like how to laugh from the seals. And when he grew up he took on the family uniform consisting of a red suit trimmed with white. He goes down to a small village and discovers that the evil town mayor burgermeister miesterburger is outlawing toys because he tripped on one. Kris of course finds this to be abominable and finds various ways to deliver toys to the children, which explain the Santa we know such as stockings and the chimney bit. He also befriends the evil wizard in the woods, who loses his powers after he becomes good, and this wizard gives some reindeer magic corn to help them get out of a tight spot. Eventually toys become accepted and Santa is no longer an outlaw and can deliver toys in peace.
http://www.youtube.com/watch?v=mknYnLo8Tb4
The Year Without a Santa Claus (1974)- One year santa decides that no one in the world cares about Christmas anymore, that there's no real Christmas spirit alive in the world anymore. So he decided that no one would miss him come Christmas eve and planned to take a holiday instead of deliver presents to people who didn't care anymore. So Mrs. Claus sends two elves down to find some Christmas spirit. The elves also run into the heat miser and the snow miser, two beings that control the elements of fire and ice, and they get into some trouble with them. Eventually they do find some Christmas spirit and show it to Santa just in time for him to suit up and go about his duties. Classic.
http://www.youtube.com/watch?v=dPrbccEdI5o
Frosty the Snowman (1969)- The story of a snowman that comes to life one Christmas due to the help of some children and a magic hat. The snowman and one of the young girls run away to the north pole to escape the magician who owns the magic hat and wants to take it back now that he knows it's worth something. There are sequels but in my personal opinion this is the only one worth watching.
http://www.youtube.com/watch?v=pmuJDmjq-xQ
Christmas Comes But Once A Year (1936)- This short film features Grampy from Betty Boop. He passes by an orphanage on Christmas and hears very loud crying. This is because all of their toys broke because they we cheap. So typical Grampy sneaks into their house and makes them toys out of random kitchen objects and they are all happy in the end.
http://www.youtube.com/watch?v=d4y8wj01MmU
Santa's Surprise (1947)- This is a Little Audrey episode where Audrey and kids from all around the world decide to give Santa a present one Christmas and clean his house for him. It is extremely racist but cute otherwise.
http://www.youtube.com/watch?v=dOSZOhpuhfM
The Snowman (1982)- A beautifully touching short about a boy who makes a snowman that comes to life one night. The boy and the snowman have fun around the boy's house and after that fly up to the north pole where they join the snowman ball and even meet Santa. The snowman then takes the boy home and the boy goes to bed, and when he wakes up the next morning he finds that the snowman has melted. It's very sad, when my younger brother was a toddler he actually cried watching this. The entire film is wordless, the soundtrack compliments the action and the song as they fly to the north pole is one of the best parts, it's Walking in the Air by Blake.
http://www.youtube.com/watch?v=ubeVUnGQOIk
Toy Tinkers (1949)- Chip and Dale spot Donald Duck cutting down a christmas tree and follow him home. When they look into his window they see all of the Christmas goodies he has and end up having a war with him for the nuts and sweets
http://www.youtube.com/watch?v=miEi3F8s8H8
Pluto's Christmas Tree (1952)- Another episode with Chip and Dale, only this time they see Mickey and Pluto out looking for a good tree to chop down and after taunting Pluto, hide in the tree Mickey chooses. They take a short nap and when they wake up the tree is almost completely decorated and they find themselves in a colourful magical place. Pluto spots them after they have some fun with the ornaments and eventually Mickey finds them and welcomes them.
http://www.youtube.com/watch?v=jKVuL6xi8Rk&feature=related
Donald's Snow Fight (1942)- Donald bundles up to go sledding on a cold winter day and harasses the triplets and causes a huge snow fight.
http://www.youtube.com/watch?v=ZCjokrhNXCE&feature=related
Hector's Hectic Life (1948)- A dog's owners go out for a bit leaving his strict instructions not to mess up the house. He finds some puppies they make a mess of the house. The owners come home and are ready to thrown out the dog into the cold but the puppies come out and defend him. The owners are so happy to find puppies that they forgive the old dog.
http://www.youtube.com/watch?v=IfIkjQkm79c
A Christmas Carol (1999)- The one with Patrick Stewart.
http://www.youtube.com/watch?v=upAYkFugbco&feature=related
A Christmas Carol (1984)- Another one that's good.
http://www.youtube.com/watch?v=Kcq6y496nrI&feature=related
A Christmas Carol (1951)- And yet another one. Also very good.
http://www.youtube.com/watch?v=SpbthuKFuFA&feature=related
Tenth Avenue Angel (1948)- Flavia has been told that her aunt's fiance has been travelling the world, but in reality he's been in prison. When she finds this out she loses faith in everything she's ever believed including her family and god and only a miracle will change her mind. She finds a model cow on its knees in the nativity scene and asks why and her mother tells her that all cows kneel at 12 o'clock on Christmas morning. She of course doesn't believe this, but goes on a wild quest to find out whether or not it's true. She does find a cow kneeling when the time comes, but this is an interesting story about telling children things we don't believe, or even things we do, and why, even though they tell her some whoppers (though it doesn't go into the why of course. That's more for you to think about).
http://www.youtube.com/watch?v=w5qZRlfJBR0
Mickey's Christmas Carol (1983)- Mickey takes on the Dickens classic and does a pretty good job of staying retelling the story.
http://www.youtube.com/watch?v=eCO4D7KTRtE
The Nutcracker Prince (1990)- A great version of the story. One of my favourite.
http://www.youtube.com/watch?v=D0tmsTJywAI
Barbie in the Nutcracker (2001)- After her nutcracker's battle with the rats in her house, Barbie goes on a journey in a sugary wonderland to save the prince and defeat the rat king. Great adaptation.
http://www.youtube.com/watch?v=FslsVu2Z8d0
Barbie's Christmas Carol (2008)- The story is a little bit altered, but it's still good and gets the message across. Eden is a successful opera singer who is very selfish. She gets angry at her stage group and says that f they don't cancel their Christmas plans the practice their next performance they'll be fired. So her dead aunt visits her and sends her three ghosts, etc.
http://www.youtube.com/watch?v=-YSCuKARLi8
Elf (2003)- The story of a human who was raised by elves decides to go to New York to find his father and inspire Christmas cheer in all that he meets
http://www.youtube.com/watch?v=pvtmsqyOkhc
It's A Wonderful Life (1946)- The story of a man at the end of his rope who is about to commit suicide. An angel intervenes shows him what the world would be like if he wasn't in it and what he has to be grateful for.
http://www.youtube.com/watch?v=LJfZaT8ncYk
The Polar Express (2004)- The story of a boy who is almost at the age where he is about to stop believing in Santa. He's invited to go on a magical train ride to the north pole and see Santa and Santa gives him a bell that can only be heard by people who believe.
http://www.youtube.com/watch?v=jVfB6GhlwIM
Mole's Christmas (1994)- Mole and Rat from Wind in the Willows are on their way back to Rat's house when Mole smells his old home. The pair find the home and end up spending Christmas there.
http://www.youtube.com/watch?v=2DxgtFoo_zk
How The Grinch Stole Christmas (1966)- The story of the Grinch, who hates Christmas and tries one year to stop it from happening. In the process he finds that Christmas is more than the stuff.
http://www.youtube.com/watch?v=XYRnwWmteac
How the Grinch Stole Christmas (2000) - The live action version.
http://www.youtube.com/watch?v=Pl12cnQxAaU
Miracle On 34th Street (1947)- An old man claiming to be Santa Claus tries to convince a young girl and her mother that he exists. In the process he assaults someone and ends up going to court. Interesting trailer to say the least.
http://www.youtube.com/watch?v=0IZr_SvCcXc
Miracle On 34th Street (1994)- Pretty much the same but they change up the climax of the courtroom scene.
http://www.youtube.com/watch?v=yiypbCFV7Ao&feature=related
White Christmas (1954)- Two ex-GIs and two sisters go to an inn and sing and dance. Basically. It's not the most exciting Christmas movie, but I end up watching it every year.
http://www.youtube.com/watch?v=AB1ZD6JKxes
Merry Christmas, Mr. Bean (1992)- The funniest Christmas show ever. Ever.
http://www.youtube.com/watch?v=AB1ZD6JKxes
Christmas in Connecticut (1945)- A woman who write the most successful column in a magazine about her life as a mother and cook on a farm in Connecticut, but in reality she's a single woman living in the city. This becomes a problem when a nurse asks the magazine if a wounded solider can spend christmas with her so that he'll marry the nurse, and the owner says that that should be fine and he ends up going too. The woman is in some trouble here because she cant cook and only has an apartment, so she promises to marry a wealthy man who has been trying to persuade her to marry him for many years. She also brings along a chef friend who cooks. The whole weekend is a series of close calls and romance.
http://www.youtube.com/watch?v=YVTF5XIpqL0
Home Alone (1990)- A boy gets left behind when his family goes on vacation and he has to booby trap his house to get to better of a couple of bandits.
http://www.youtube.com/watch?v=CK2Btk6Ybm0
Home Alone 2 (1992)- This time the boy goes on vacation with his family, but get separated at the airport and ends up going to New York instead of Miami. He runs into the bandits again. Home alone movies end here.
http://www.youtube.com/watch?v=z_An3W-oO2k&feature=related
Mickey's Once Upon A Christmas (1999)- A collection of three short stories. In the first Hugie, Dewie and Lewie learn that it's better to have one Christmas with the people you love than a million Christmases with only your toys. In the second Max and Goofy work out whether or not they believe in Santa Claus and whether or not it matters, and the third is Mickey and Minnie in the story of the gift of the magi.
http://www.youtube.com/watch?v=1-mJwHb8kQc
The Little Match Girl (2006)- A poor girl tries to sell matches on the street and sees visions or a happier life before she dies.
http://www.youtube.com/watch?v=yUSzQBaWq0Q&feature=related
The Santa Clause (1994)- A man kills Santa and subsequently becomes him.
http://www.youtube.com/watch?v=cOsE81woec4
Santa Claus (1985)- There is a prophecy of a master toy make who will come to the North Pole but an elf goes to a consumeristic man for help and he tries to commercialize the north pole.
http://www.youtube.com/watch?v=6hbX_fRgzqk
The Nutcracker (1993)- This is basically the ballet on film, but it's still great to watch.
http://www.youtube.com/watch?v=Bgbw_zfPB-Y&feature=related
The Secret of the Nutcracker (2007)- This is a contemporary adaptation of the Nutcracker set in the 40's. The girl deals more with her father's absence due to the war than she does some magical quest to help out her wooden doll.
http://www.youtube.com/watch?v=7bTrKmSDlPQ
A Charlie Brown Christmas (1965)- Charlie Brown gets fed up with the commercialism of Christmas and tries to celebrate Christmas how he thinks it should be celebrated, which fails until his friends come to help.
http://www.youtube.com/watch?v=L8N6d0oIEzw&feature=related
Nightmare Before Christmas (1993)- The king of Hallowe'en town discovers Christmas and tries to bring it home with him.
http://www.youtube.com/watch?v=8qrB9I3DM80
The Small One (1978)- A boy has to sell his donkey because he's getting old but the only one in town who needs a donkey is the tanner. Just when all seems hopeless a man comes up to the boy and asks to buy the donkey to carry his wife to Bethlehem.
http://www.youtube.com/watch?v=JGTjbSS8hSc
The Holiday (2006)- Two women switch houses to escape their lives for a while and meet men while they're away.
http://www.youtube.com/watch?v=G0p8Su3bdHc
The Family Man (2000)- A man is given a glimpse of what his life would have been like if he'd chosen having a family over a career.
http://www.youtube.com/watch?v=My7Fb0cI1Gc