Few things in contemporary society are as divisive as holiday music. For some, it is a warm reminder of happy times with family, while for others it is the soundtrack to a season filled with massive amounts of stress and expense. If you’re in the latter category, you probably want to run as far away from anything that remotely resembles holiday music, but would you be open to the possibility that there are some holiday (and holiday-adjacent) songs that deviate from your typical radio Christmas standards? The songs below, while perhaps not as overwhelmingly cheerful as “Santa Claus is Coming to Town” or “All I Want for Christmas is You,” are some of the strongest arguments that there are cool songs to go with whatever end-of-the-year festivities you observe.

It should be noted that for the purposes of this list, all the songs below are originals, not covers (that would be a separate list). Also, while the beautifully cynical “Fairytale of New York” by The Pogues is still a classic to many, it has been excluded from this list for some problematic lyrics and the fact that it’s sort of the cliché go-to for cool anti-Christmas-song Christmas songs.

For more great music, make sure to check out the offerings of your local Library branch and Freegal.

“Christmas Rappin’” by Kurtis Blow (from the album, Kurtis Blow)

Maybe you know Kurtis Blow from the trailblazing hip hop classic, “The Breaks,” but before that, he released this delightful holiday jam (which predated Run-DMC’s “Christmas in Hollis” by almost a decade). It definitely sounds like an old-school hip-hop song, but there’s beauty in its simplicity. Perhaps most importantly, it set a precedent that no occasion was off limits to rap—just as Santa intended.  

Best Lyrics: Bout a red-suited dude with a friendly attitude/ And a sleigh full of goodies for the people on the block/ Got a long white beard, maybe looks kind a weird/ And if you ever see him, he could give you quite a shock 

“Christmas Vacation” by The Descendents (from the album, I Don’t Want to Grow Up)

Between the speed of hardcore punk, a commitment to both melody and humor, and singer Milo Aukerman’s nerdy, self-deprecating persona, The Descendents’ influence cannot be overstated. In many ways, they codified many of the elements of ‘90s skate punk and turn-of-the-century pop punk. While The Descendents are often remembered for snotty, ironic anthems like “Suburban Home,” it’s worth remembering that they also have a snotty, ironic Christmas song. With “Christmas Vacation,” Milo and the gang take us on a wild ride that’s one part Christmas, fifteen parts misery.  

Best Lyrics: You took a vacation into oblivion/ You were so low and I felt like I didn’t know you/ Christmas vacation, you took a vacation from me, oh-oh-oh/ From me, oh-oh-oh