Holiday Music’s Naughty List: The Worst Songs of All Time

Holiday Cheer Meets Holiday Cringe

The Christmas season brings twinkling lights, cozy traditions — and, inevitably, a handful of songs that test even the most festive spirit. While holiday classics can feel timeless, the tracks that land on the wrong side of the “nice list” tend to spark debate, frustration, or outright groans. USA TODAY’s Melissa Ruggieri tackled that challenge head-on, assembling a definitive ranking of the 10 worst Christmas songs of all time.

Some choices are obvious targets, while others are controversial picks that fans defend passionately. Even well-known tunes with nostalgic pull aren’t immune to scrutiny, including Paul McCartney’s “Wonderful Christmas Time,” which some listeners adore and others consider relentlessly sappy.

Debates Around Holiday Staples

Songs like “Baby, It’s Cold Outside” continue to stir disagreement, though Ruggieri notes that the song’s origins — written by Frank Loesser to perform with his wife — offer important context. Still, many holiday favorites suffer from overexposure, questionable lyrics, or creative misfires that land them firmly in the “please skip” category.

From novelty acts to forgotten boy-band experiments, the list ranges from the strange to the saccharine. Tracks from The Killers, Lou Monte, Jessica and Ashlee Simpson, and NewSong all earn recognition as seasonal offenders, each for their own unique reasons — whether it’s odd storytelling, clashing arrangements, or emotional manipulation.

And the “Worst” Crown Goes To…

Alvin and the Chipmunks top the ranking with “The Chipmunk Song (Christmas Don’t Be Late),” a track Ruggieri jokingly describes as pure sonic chaos. With its shrill, high-pitched delivery, the song is cited as the ultimate example of a holiday tune capable of sending even devoted Christmas lovers racing for the volume knob.

Love them or hate them, these songs prove one thing: holiday music has range — from magical to maddening.