Pretty Paper- Roy Orbison
A Christmas Song about a Christmas Paper Salesman who no one pays any attention to, and he feels lonely in the midst of the Holiday Season. This song was written by Willie Nelson. For Roy Orbison's #1 fan @llorando
If We Make it Through December- Merle Haggard
This song is about a laid-off factory worker who can't afford Christmas and His daughter cannot understand why.
The Christmas Shoes-Newsong
Quite possibly the saddest Christmas song and most despised because of the sadness.
Happy Christmas (War is over)- John Lennon
It Could Happen Again (Christmas 1914)-Johnny Cash and Collin Raye
This song tells the story of the World War 1 Christmas Truce that lasted for 2 days amongst British Empire, French, and German Soldiers.
Christmas is meant to be happy, but sometimes there are Christmas songs which are rather sad and have a good message to them.