1. The Residents, “Santa Dog” (1972)
No song can trigger an obsession with strange holiday music better than the very first single issued by the mysterious, deeply weird masked musicians known as The Residents. From its snarling opening to its irresistible sing-along falsetto chorus (“in the FUTURE!”), this bizarre tale of the “Jesus fetus” is a classic just waiting for sanction. Special bonus lunacy: The Residents sent a copy of the song to Richard Nixon for Christmas 1972. His reaction, sadly, is unrecorded by history.
Availability: The Residents have released many versions of “Santa Dog” over the years. This is the original, also known as “Fire,” but other versions can be had on disc or download.
2. Frosty & The Fun Street Gang, “Santa Claus Is Discoin’ To Town Tonight” (1982)
This thrift-store find features everyone’s favorite living snowman traveling the country with the Fun Street Gang, presumably a group of reformed Crips he’s saved from a life of crime and transformed into what he describes, with wonderful blitheness, as “a funky little five-piece band.” Together, they belt out this catchy little holiday number, which is either three years too late for the original disco craze or six years too early for its revival, depending how charitable you are toward Mr. The Snowman.
Availability: Way, way, way out of print. Thrift stores & eBay are the only places you’re likely to dig this one up.
3. Heather Noel, “Santa Came On A Nuclear Missile” (1974)
In its 1960s and 1970s heyday, the American Song-Poem Corporation catered to the millions of Americans whose hobby was writing terrible poetry. For a small fee, the company would set such terrible poems to music, ground out at a rate of dozens per day by embittered studio rats like the pseudonymous “Heather Noel.” And for some reason, nothing inspired terrible poets like Christmas—hence the prevalence of songs like this one, alternately sweet and incredibly disturbing.
Availability: Available on disc or download as part of Daddy, Is Santa Really Six Foot Four?: The American Song-Poem Christmas (Bar/None).
4. Frank Sidebottom, “Christmas Is Really Fantastic” (1986)
Uniquely British and inexplicably charming, Frank Sidebottom—created by ex-punk rocker Chris Sievey—is a hulking, childlike Timperley football supporter with a gigantic papier-mâché head. He enjoys toy robots, Queen songs, and bickering with his sidekick, a mannequin named Little Frank. One of his earliest efforts was an EP of holiday tunes, anchored by this ridiculously catchy song about all the ways the holiday season is, well, fantastic.
Availability: The original is long out of print, but downloads can be had from Amazon, iTunes, or eMusic on the compilation A, B, C & D: The Best Of Frank Sidebottom (Cherry Red).
5. Randy Newman, “Christmas In Capetown” (1983)
In spite of the cuddly image he’s developed as a result of his work on Disney films, Randy Newman built his reputation with deeply dark, cynical character studies of human grotesques. For “Christmas In Capetown,” one of the grimmest holiday songs ever, he gives voice to an aging white racist from South Africa who can’t understand that history is very quickly passing him by. Smart, savage, and still a lot more relevant than it should be, this one is ideal for when the season starts to curdle.
Availability: From Newman’s album Trouble In Paradise (Warner/Reprise), which is out of print, but still available for download from the usual suspects.
6. The cast of Futurama, “The Elves’ Xmas Song” (2001)
The writers of Futurama claim that they never battled with network censors more than they did for Christmas episodes, and it isn’t hard to see why. Their vision of the holiday as an occasion for fear and terror, lorded over by a homicidally insane Santa Claus robot, isn’t typical late-December TV fare. But the fight was worth it; “Xmas” episodes have produced some of Futurama’s biggest laughs, including this work song by Santa’s toy-making elves. Who wouldn’t love singing along with the line “You selfish little bastards”?
Availability: Fat chance getting hold of this one, unless someone invents a magical device that would allow the recording of audio tracks from a television show!
7. Loretta Lynn, “To Heck With Ole Santa Claus” (1966)
Loretta Lynn’s sweet country songs have always had a bit of a nasty edge, from the brutal kiss-off of “Fist City” to the no-means-no anthem “Don’t Come Home A-Drinkin’.” This deceptively sweet-sounding holiday number, penned by Lynn herself, contains the fury of a woman scorned at Christmas: After getting stiffed for a present, she threatens jolly ol’ St. Nick with a panoply of revenge scenarios, including falling in the snow, receiving a beating, and getting burned to death after he comes down the chimney. Hopefully her husband got the message.
Availability: Even the re-release of the album this was on is out of print, but inexplicably, Amazon has it available for download.
8. Stompin’ Tom Connors, “The Snowmobile Song” (1974)
Though not technically a Christmas song, “The Snowmobile Song”—by Canadian folk hero/ultra-patriot/country singer Stompin’ Tom Connors—is a perfect way to get in the mood for winter. With its rollicking tune, cheery conjuration of a frosty wonderland, and conception of Canada as a place where lovely ladies have a special place in their hearts for any fella who knows his way around a motorized sled, it’s a perfect way to kick-start dreams of a white Christmas, even if it’s 70 degrees outside.
Availability: This wasn’t one of Stompin’ Tom’s big hits, so it’s hard to track down even if you don’t live in Canada. If you live in the U.S., well, good luck.
9. Akim & The Teddy Vann Production Company, “Santa Claus Is A Black Man” (1973)
At the height of the black-is-beautiful trend, songwriter-producer Teddy Vann (a Grammy winner who wrote hit songs for Luther Vandross and others) teamed up with his ridiculously adorable daughter Kimmy for the loopy, charming “Santa Claus Is A Black Man,” described perfectly by blogger/critic Gordon Winslow as “sort of an Afrocentric take on ‘I Saw Mommy Kissing Santa Claus’.”
Availability: Out of print for ages, but John Waters included it on his disc-or-download anthology, A John Waters Christmas.
10. Steve Martin, Paul Simon, and Billy Joel, “Silver Bells” (1980)
The origin of this semi-legendary bootleg is a bit of a mystery. Most sources claim that it’s an outtake from an episode of Saturday Night Live, but Martin and Simon were never on the same show at the same time. Further complicating things, Billy Joel—in a magazine interview from 2001—claims that it’s him playing the piano, and that it wasn’t for television at all, but merely the three of them, lubricated on wine, goofing around in a recording studio. Whatever the case, it’s hands-down the funniest version ever made of this classic carol.
Availability: Never officially released, but bootlegs abound on the Internet.
11. Eilert Pilarm, “Silent Night” (1998)
What’s better than a Swedish Elvis impersonator? Okay, what’s better than a Swedish Elvis impersonator who neither looks nor sounds anything like Elvis? What if he also records his tributes to the King over cheap karaoke tracks, and he can’t sing in any sense of the word? Now how much would you pay? Okay, what if he threw in this endearingly awful version of a beloved Christmas song, and put it on an album with one of the worst covers in the history of graphic design? Ladies and gentlemen: Eilert Pilarm.
Availability: Available on the Eilert Is Back! and Eilerts Jul albums, both out of print in the U.S.
12. Joseph Spence, “Santa Claus Is Comin’ To Town” (1972)
The legendary Joseph Spence, a Bahamian minister and folksinger, is a genuinely great talent, known for his masterful guitar work. In addition to his folk, soul, and spiritual songs, though, he also enjoyed recording deeply weird versions of popular rock songs, pop standards, and Christmas carols—hence this loony version of another holiday classic. Over his characteristic drop-tuned acoustic guitar, Spence rumbles out a song whose lyrics he clearly doesn’t know—and just as clearly doesn’t care about. Playing this on the P.A. system in shopping malls would make the whole season more enjoyable.
Availability: Available on disc or download as part of the just-reissued collection of live Spence songs, Living On The Hallelujah Side (Rounder).
13. John Prine, “Christmas In Prison” (1973)
Always slightly askew for a country singer of his generation, John Prine was capable of writing songs that were alternately hilarious and incredibly touching. He proved that with his first attempt at a holiday song; its narrative about a convict longing for his sweetheart on Christmas Eve veers between comical details of prison life (“We had turkey, and pistols made out of wood”) and throat-catching, lovely expressions of love (“her heart is as big as this whole goddamn jail”). To be played with loved ones nearby.
Availability: From Prine’s album Sweet Revenge (Atlantic/WEA), re-released in 1990 and widely available on disc or download.
14. Paddy Roberts, “Merry Christmas You Suckers” (1962)
Now largely out of fashion, Paddy Roberts once enjoyed a fair amount of success in the UK as something of a poor man’s Noel Coward. His stuff maintained the form of Coward’s urbane, sparkling musical-comedy, but his material was generally more ribald and earthy, in spite of his genteel piano-playing and toffy accent. This is an enjoyably cynical little holiday number he recorded in the early ’60s, when it briefly became so popular, it was his only release to be made widely available in America.
Availability: Pretty much impossible to find in the U.S., where it was released as “And A Happy New Year.” A bit easier to get across the pond, but it’s still a rarity.
15. Fishbone, “Slick Nick, You Devil You” (1987)
Punk and indie bands have made a tradition of recording holiday songs, but Fishbone got there first with a swell EP of original Christmas music called It’s A Wonderful Life. Putting on an aggrieved soul-man voice, Angelo Moore bitterly croons (over minimalist organ and handclaps) about his disappointing encounter with a foul-mouthed, chain-smoking, drunken Santa Claus, “cussin’ and carpin’ and playin’ punk rock.” Rarely has such extreme disillusionment sounded so delightful.
Availability: Out of print, but it can be downloaded on eMusic, Amazon, or iTunes as part of the Fishbone 101: Nuttasaurusmeg Fossil Fuelin’ The Fonkay anthology.