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Updated: Dec. 6, 2008:

Updated: Dec. 16, 2008:

Click here for “Ten more depressing Christmas songs.”

This list of sad Christmas songs first ran as a feature in Creative Loafing, back when it was the Weekly Planet, in 2002. I then re-posted it here at TampaCalling last December.

Unfortunately, the list is again proving appropriate, even more this year than during any holiday season in my lifetime. So, I decided to revive the entire article that ran in the old Weekly Planet under the title “Blue Christmas: Songs to avoid (or wallow in) for the season.” Cheers.

Originally published 12.18.02:

As anybody living on this side of a Rockwell canvas already knows, the holidays aren’t always the happiest time of the year. If you’re strapped for cash, feeling lonely or disenfranchised, Christmas usually ushers in as much grief as joy. So, to help deal with the potential doldrums of this week of all Madison Avenue weeks, here’s a list of 12/25 songs from the past three decades that wittily reflect — in no uncertain terms — the occasionally grim realities of the season. (Such pre-rock classics as “White Christmas” harbor nearly as much melancholy as merriment, as well, but Jewish composers like Irving Berlin buried the sentiment a bit deeper in the subtext than today’s songwriters.)

The alphabetically listed tunes posted below range from poignant (”Pretty Paper”) and irreverent (”Fairy Tale of New York”) to humorous (”The Christians and the Pagans”) and morbid (”Brick”) — the overriding criteria for the selections being reality-based storytelling traditionally missing from the standard holiday fare. And although John Lennon’s “Happy Xmas (War is Over)” made the cut, political songs with less universal emotional gravity — Steve Earle’s “Christmas in Washington,” Randy Newman’s “Christmas in Capetown” — were deemed unworthy. As was Elvis’ generic “Blue Christmas” and the well-intentioned but nauseating 1980s sap-fest “Do they Know It’s Christmas.”

Included after the artists’ name is the best budget album on which to find each title. This little perk is just in case you’re looking for that special depressing something to send your ex. You know, just to remind him or her of just how much misery they’ve caused you during this season of supposed Yuletide spirit.

“Brick” Ben Folds Five, Whatever and Ever Amen The economically challenged protagonist rises at “6 a.m. the day after Christmas” to drive his young girlfriend to the abortion clinic. Now how’s that for holiday cheer? Killer Line: “They call her name at 7:30/ I pace around the parking lot/ Then I walk down to buy her flowers/ And sell some gifts that I got.”

“The Christians and the Pagans,” Dar Williams, Mortal City How about a little humor before blowing our brains out? In this astute comedic sketch from Williams, two related families polarized by religious differences come together for a holiday meal and try to agree that “Christmas is like solstice.” Killer Line: “The food was great, the tree plugged in, the meal had gone without a hitch/ Till Timmy turned to Amber and said, “Is it true that you’re a witch?”

“Christmas in Prison,” John Prine, Sweet Revenge John Prine is one of few songwriters who could take such clichéd country-music terrain as prison, heartache and Christmas, and come up with something that smacked of true sincerity — no big surprises, but genuinely moving. Killer Line: “It’s Christmas in prison/ There’ll be music tonight/ I’ll probably get homesick/ I love you/ Goodnight.”

“Fairytale of New York,” The Pogues, If I Should Fall From Grace With God A homeless couple’s dialogue begins cheerily but by the end of this four-minute exchange, vile nastiness prevails. Killer Line: “You’re a punk/ You’re an old slut on junk … You scum bag/ You maggot/ You cheap lousy faggot/ Happy Christmas your arse/ I pray God/ It’s our last.”

“Happy Xmas (War Is Over),” John Lennon, John Lennon Anthology The man who said his band was bigger than Jesus Christ, and then got a nice little ribbing from the American right, gets his revenge by using the ol’ Christian-taunting “Xmas” in the title of a hit song reminding everyone how shitty life is. Killer Line: “And so this is Xmas/ For weak and for strong/ For rich and the poor ones/ The world is so wrong.”

“If We Make It Through December,” Merle Haggard, If We Make It Through December This is Haggard’s holiday twist on his patented “Workingman Blues” theme — a real beauty marked by strong source material, smart production and sensitive vocals. Killer Line: “I don’t mean to hate December/ It’s meant to be the happy time of year/ But my little girl don’t understand/ Why daddy can’t afford no Christmas here.”

“Merry Christmas From the Family” Robert Earl Keen, Gringo Honeymoon Easily viewed as xenophobic and perhaps borderline racist in today’s hypersensitive climate — “Little sister brought her new boyfriend/ He was a Mexican/ We didn’t know what to think of him/ Till he sang ‘Feliz Navidad’” — the song is also a humorous tale of the Christmas Vacation variety, emphasizing the importance of tolerance. At least among kin and their significant others. Killer Line: “Send somebody to the Quik-Pak store/ We need … a can of bean dip and some Diet Rite/ A box of tampons and some Marlboro Lights.”

“Pretty Paper,” Roy Orbison, The All-Time Greatest Hits of Roy Orbison Paired with Orbison’s tortured warble, this Willie Nelson-penned bad-love ballad expresses bitterness with a subdued maturity foreign to the country and pop/rock music of the era (it was a hit for Orbison in 1963). Killer Line: “In the distance the ringing of laughter/ And in the midst of the laughter he cries.”

“The River” (a.k.a. “It’s Coming on Christmas”), Joni Mitchell, Blue The slow, off-key “Jingle Bells” intro is the perfect prelude to one of the saddest Christmas songs ever. Killer Line: “I made my baby cry.”

“The Last Thing I Needed First Thing This Morning,” Willie Nelson, Legendary Country Singers, Time-Life Music The cuckolded singer knowingly tolerates his woman’s infidelities because her love makes him “feel complete” and he doesn’t want to spend Christmas alone. Of course, she walks anyway. Nelson didn’t write this one but he emotes as if the incident happened to him shortly before committing the song to tape. Killer Line: “Last night you came home and I knew you’d been drinking/ By that old mellow look on your face/ But I thought it don’t matter because it’s the holiday season/ And you fill such a big, empty space.”

Joni Mitchell — “The River”

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