One of the first albums I listen to every Christmas season is Elvis Presley's "If Every Day Was Like Christmas," an album that captures what my mother-in-law calls Elvis' "warbling" stage. It is melodramatic and overcooked, and I love it. It is at once dour and delightful, which is how I like my Christmas music.
I love straight-up joyful Christmas carols, too, and ridiculous songs like Bing Crosby's "Snow." But sad Christmas songs capture the lower register of feelings that usually accompany the season, from nostalgia and longing to frustration and winter flu.
Below you'll find my (Elvis-heavy) list of Top Ten Delightfully Depressing Christmas Songs. This list avoids the many, many intentionally creepy Christmas songs. Well, mostly--the last entry requires some explanation, which you'll find at the bottom of the post.
Be sure to tell me what I missed!
2. Do They Know It's Christmas? - Original Band Aid version
3. The River - Sarah McLachlan version
4. Last Christmas - WHAM!
5. Happy Christmas (War Is Over) - John Lennon version
6. Holly Leaves and Christmas Trees - Elvis Presley
7. Christmas (Baby Please Come Home) - U2 version
8. It Won't Seem Like Christmas Without You - Elvis Presley version
9. I'll Be Home on Christmas Day - Elvis Presley version
10. Baby It's Cold Outside - Leon Redbone and Zooey Deschanel*
*This is a recent entry to my list, because the other day a friend sorta ruined it by pointing out that this version with Zooey Deschanel and the legendary Leon Redbone has a whiff of Lolita about it. His aging voice combined with the young chanteuse gives a nasty edge to lines like "My mother will start to worry / My father will be pacing the floor." It also sounds like he's trying to get her stoned: "Say, what's in this drink?" Also, Wikipedia notes that Sayyid Qutb, the Islamic intellectual who attended college at the University of Northern Colorado and whose writings helped shape modern-day Islamist terrorism, cited the song as part of his critiques of the moral failings of Americans.

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A delightful list, I am listening to one of your picks right now! I hope you have heard Elvis Presley Christmas Duets. You can read all about it at a page that I have written http://www.squidoo.com/elvispresleychristmasduets and you can actually record your own voice singing with the King to Blue Christmas! It was a lot of fun (even though I cannot sing) and you can read all about recording with Elvis at http://www.squidoo.com/singwithelvispresley .
Brenda
Blue Christmas is the one song that will cause me to change radio stations faster than any song ever made. I despise it. Ick.
Patton - how about "Please Daddy (Don't Get Drunk This Christmas)" - I heard the Alan Jackson version though I gather John Denver started this mess.
What!? No one mentioned Jill Sobule's _Christmas is the Saddest Day of the Year_!?
Not sure how I feel about these computer made duets with dead artists ?
I love the King and I'm all for bringing his music to new fans, but cant help but feel these duets would make him turn over
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