4. The Handsome Family: “So Much Wine”
I have Phoebe Bridgers to thank for this one: It was her pick last year in her annual Christmas covers series. I’d never heard the original, and when I went back to check it out, I found that I actually preferred it to Bridgers’s more mournful rendition. Her version of this ballad of seasonal alcoholism is an out-and-out tear-jerker, but the Handsome Family manage to tell the same story with some dark comic relief. (Listen on YouTube)
5. Taylor Swift: “’Tis the Damn Season”
I believe it was my colleague Joe Coscarelli who, on an episode of Popcast, came up with one of my favorite Taylor Swift conspiracy theories: That “Evermore,” her second and decidedly more wintry 2020 album, was originally supposed to be a Christmas-themed release. This finely wrought ode to hometown what-ifs and temporarily rekindled romance is probably the strongest argument for that case. (Listen on YouTube)
6. The 1975: “Wintering”
Here’s another song about regressing at one’s parents’ house for a long weekend, a curiously season-specific track on the 1975’s excellent 2022 album “Being Funny in a Foreign Language.” I often appreciate the details in Matty Healy’s writing, and there are some particularly vivid ones here: a precocious, vegan sister; a fleece that doesn’t warm as well as advertised; a mother with a sore back who objects to being mentioned in the song. “I just came for the stuffing, not to argue about nothing,” Healy sings. “But mark my words, I’ll be home on the 23rd.” (Listen on YouTube)
7. Barbra Streisand: “My Favorite Things”
Written by Richard Rodgers and Oscar Hammerstein for the 1959 Broadway production “The Sound of Music,” “My Favorite Things” didn’t begin life as a holiday song. Julie Andrews performed it on a 1961 Christmas special, though, and since then its mentions of mittens, snowflakes and brown paper packages tied up with strings have made it sound at home on many a Christmas album — including Barbra Streisand’s. (Listen on YouTube)
8. Leonard Cohen: “Hallelujah”
Speaking of famous Jews singing are-they-really-Christmas songs, the endlessly over-covered, richly poetic, mordantly hilarious “Hallelujah” is in so many ways one of the most misunderstood songs in popular culture — so of course some people have turned it into a holiday standard. But as Stereogum’s Chris DeVille wrote in a 2019 essay, vehemently and correctly, “Whatever context it belongs in, Christmas ain’t it.” (Listen on YouTube)
9. The Pogues featuring Kirsty MacColl: “Fairytale of New York”
This is probably the only true Christmas song on the list, but it’s certainly an unconventional one — and of course I had to include it in honor of the Pogues’ Shane MacGowan, who died last week. Over the weekend, Rob Tannenbaum (a journalist with a very appropriate name for this purpose) published a fascinating piece about the making of the song, and the push to send it to the top of the charts in the United Kingdom. Might “Fairytale” be the next Christmas song to belatedly hit No. 1? (Listen on YouTube)
