Illustration by Jillian Tamaki.

This story originally appeared in December 2005.

It’s not Christmas I despise, it’s the soundtrack. As intrinsic to the holiday season as rock-hard fruitcakes, spiteful crowds and overpriced photo ops with mall Santas, Christmas singles creep onto radio playlists in mid-November and don’t stop chiming until the New Year. (There are even stations that devote the entire month of December to holiday music, but the less said about them, the better.)

There’s no shortage of pop singers willing to take a crack at an old chestnut or — heaven forfend! — compose a new one. Here are some of the worst holiday offerings.

Jingle Bells, Frank Sinatra (1957)

Frank Sinatra was known for his smooth phrasing and relaxed delivery. On this hoary carol, Ol’ Blue Eyes sounds like Ol’ Shut-Eye; his performance is utterly soporific, and not in a charming, Perry Como sort of way. Sinatra’s backup singers take liberties with the chorus (“J-I-N-G-L-E bells!”), which has the adverse effect of turning the song into a spelling tutorial.

(Sony Music Canada)

All I Want for Christmas Is You, Mariah Carey (1994)

The feeling is not mutual, Mimi. Carey’s contribution to the Christmas canon (she co-wrote the song) is full of syrupy string flourishes and Carey’s usual vocal palpitations. In other words, not unlike the Jingle Cats (see below).

I Saw Mommy Kissing Santa Claus, John Cougar Mellencamp (1989)

John Mellencamp does not have what one would call a “delicate” voice; in fact, his gruff delivery should preclude him from getting within 20 feet of a Christmas carol. The song’s Cajun-flavoured accompaniment (accordions, slide guitar, cowbell) has a certain zip, but Mellencamp robs this carol of all melody. The tuneless children’s chorus in the coda adds insult to an injurious outing.

Feliz Navidad, Jose Feliciano (1970)

This one’s a special kind of annoying. The buoyant Neil Diamond vibe is actually quite endearing, but that voice! Perhaps it’s residual contempt for Feliciano’s defiling of the Doors’ Light My Fire or the fact that he always sounds like he’s on the verge of sneezing, but I can’t hear this song without wanting to cancel Christmas altogether.

Happy Xmas (War Is Over), John Lennon and the Plastic Ono Band (1971)

Sleigh bells, tympanis, sighing strings — if the orchestration offers any clues, Lennon seemed intent on writing the most cloying Christmas song ever. Advocating for peace is commendable, but why not just write a poem?

(Sony Music Canada)

O Holy Night, Celine Dion (1998)

The problem with this entry isn’t the source material, but the fact that Dion thinks she’s still recording the soundtrack to Titanic. Throwing all notions of subtlety overboard, Dion belts out this hallowed carol like she was stumping for another Oscar.

Fairytale of New York, Shane MacGowan and Kristy MacColl (1987)

“It was Christmas Eve, babe / in the drunk tank.” So begins this modern-day carol, one of the slushiest holiday tunes of all time. Shane MacGowan is perfectly cast as a tippler seeking yuletide salvation, but the only thing more distasteful than looking at the Pogues frontman is hearing him warble.

Santa Claus Is Coming to Town, Bruce Springsteen (1984)

This one has always sounded more like a dare than a legitimate cover. The Boss burbles like he’s three sheets to the wind; the mincing piano vamp, on the other hand, feels almost satirical. Proof positive that during the holiday season, otherwise reasonable musicians develop a tin ear. More eggnog, Bruce?

Mary’s Boy Child, Boney M (1978)

Boney M score points for spicing this Christmas classic with Caribbean flavour, but there’s something so sterile about the vocal harmonies, steel drums and unforgiving disco beat that it never fails to make me shudder.

(Jingle Cats Music)

White Christmas, Jingle Cats (1994)

In the early ’90s, some savvy producer decided to sample his cats to sound like they were singing Christmas carols. I don’t know what irks me most: the horrific sound of digitally manipulated catsong, the cynicism of doing so or the fact that this nonsense was followed by Jingle Dogs.

Santa, Come Up to See Me Sometime, Mae West (1968)

Recorded in the late '60s, when erstwhile screen siren Mae West was in her 70s, this misguided single is characterized by creepy come-ons (“What you could give me for Christmas / is nothing to what I could give you”) and an inexplicable falsetto section. The fact that this song was intended as parody cannot disguise its fundamental awfulness.

We Wish You a Merry Christmas, Kenny G. (2005)

Kenny G.’s saxophone has done incalculable damage to jazz, to pop, to makeout music. This suffocating version of a holiday fave is his attempt to bring down Christmas. He very nearly succeeds.

Andre Mayer writes about the arts for CBCNews.ca.