If Santa listened to all of these songs consecutively, he’d probably just stay home, cry, and eat cookie dough on Christmas Eve night. Here’s my admittedly incomplete list of the saddest Christmas songs ever (along with the artist/band who popularized each song):
1) “The Least of These”—John Primm
Why you’ll weep: Despite never being released on a record, this song’s played fairly often in the Nashville area (you can hear it here). The message is good, although I’m not sure about Jesus being homeless (didn’t the Magi visit the house where He was staying?). Hope against hope that you don’t hear these lines while you’re raiding your fridge for leftover turkey: “From the shelter of a boarded door, a boy comes cross the street / Hey Santa, seeing how it’s Christmas Eve, can you spare a bite to eat?”
2) “Pretty Paper”—Roy Orbison and/or Willie Nelson
Why you’ll weep: Penned by Willie Nelson, originally recorded by Roy Orbison, re-recorded by Willie, and tear-jerking SAD when you hear, “Downtown shoppers, Christmas is nigh / There he sits all alone on the sidewalk, hoping that you won’t pass him by” and “In the distance the ringing of laughter / And in the midst of the laughter he cries.” Why is he crying? I don’t know. But I’m pretty sure it’s my fault.
3) “I’ll Be Home For Christmas”—Bing Crosby
Why you’ll weep: It’s sad enough when you’re assuming that the protagonist in the song is too busy at work to get home for Christmas…or that he’s making one last phone call to Mom after suffering a grave injury in an ill-timed car accident. It gets worse, however, when you hear “Christmas Eve will find me where the lovelight gleams / I’ll be home for Christmas, if only in my dreams” and know that it was written from the viewpoint of overseas American soldiers in World War II. Wow.
4) “I Believe in Father Christmas”—Emerson, Lake & Palmer
Why you’ll weep: If you want to feel cynical about a lot of the things you cherish about Christmas, this is a good place to start: “They sold me a silent night / And they told me a fairy story / ‘Til I believed in the Israelite / And I believed in Father Christmas / And I looked at the sky with excited eyes / ‘Til I woke with a yawn in the first light of dawn / And I saw him and through his disguise.” If you’re going to gather the family around the fireplace for a warm-fuzzy Christmas sing-along, consider skipping this one.
5) “Happy Xmas (War is Over)”—John Lennon
Why you’ll weep: This cautiously hopeful song gets to the point early. “So this is Christmas, and what have you done? / Another year over and a new one just begun…” Life just keeps marching on, people. Yeah, you’re excited and thankful for the promotion you got this year, and for Jesus being born, and for your family’s health…but exactly WHAT have you done this year to bring world peace? What’s that? Nothing? Well…do better next year.
6) One-third of Kenny & Dolly’s entire “Once Upon a Christmas” album
Why you’ll weep: It’s cheating to lump these songs together, I know, but that seems more fair than letting this power couple dominate the rankings. One of my favorite guilty-pleasure albums serves up a trifecta of sad songs, and no one sells them better than Kenny and Dolly. Two are obvious choices due to a shared “lost love” theme. The other is an upbeat ditty that’s depressing when you consider the lyrics: two strangers honor Christ’s birth by hooking up at a ski resort for a weekend of white-hot, lusty passion.
–Christmas Without You: “Christmas without you / White Christmas and I’m blue / I love you, I miss you / So sad but so true…”
–A Christmas to Remember: “And I had fantasized about Christmas in this way / Curled up by a fireplace in a Tahoe ski chalet /With a fast-talking lover with some slow-burning wood / But even in my wildest dreams it never got this good!”
–Hard Candy Christmas: “I’ll be just fine and dandy / Lord it’s like a hard candy Christmas / I’m barely getting through tomorrow / But still I won’t let sorrow bring me way down.”
7) “Do They Know It’s Christmas?”—Band Aid
Why you’ll weep: This song is the perfect example of the positive power of music…and the sadness it brings is part of why it’s so effective. “There’s a world outside your window / And it’s a world of dread and fear / Where the only water flowing is the bitter sting of tears / And the Christmas bells that ring there / Are the clanging chimes of doom / Well tonight thank God it’s them instead of you!” When Bono belts out that last line, almost anything you’re doing at the moment seems trivial.
Okay…there’s my list. Which songs did I carelessly omit? Feel free to sound off in the comments below.