The 10 Most Cringe-Worthy Christmas Songs

The Christmas season brings both joy and occasional discomfort, especially when it comes to holiday music. While some tunes fill us with cheer, others leave us cringing with every note. Here are 10 of the most cringe-worthy Christmas songs that are hard to stomach.

*10. NSYNC – “I Never Knew the Meaning of Christmas”
This song from *NSYNC misses the mark by focusing not on the Christmas spirit but on finding a girlfriend. Christmas isn’t just about romantic relationships, and this track feels out of place.

9. Neil Diamond – “Cherry Cherry Christmas”
While Neil Diamond is a legendary artist, “Cherry Cherry Christmas” feels like a marketing gimmick, with recycled lyrics from his popular hits, making it sound forced rather than festive.

8. The Killers – “Don’t Shoot Me Santa”
This strange and unsettling track features an odd conversation between Brandon Flowers and Santa. The dark, almost sinister tone makes this song a bizarre choice for a holiday anthem.

7. The Pussycat Dolls – “Santa Baby”
This version of “Santa Baby” tries to bring a seductive flair, but instead falls flat with awkward delivery and a lack of charm, especially compared to the original by Eartha Kitt.

6. Lou Monte – “Dominick the Donkey”
A quirky song about an Italian donkey helping Santa deliver presents, but it’s hard to take seriously. The repetitive lyrics and strange melody leave much to be desired.

5. New Kids on the Block – “Funky Funky Xmas”
The “funky” vibe of this song is anything but, as the boy band attempts a rap-style track that comes across as awkward and out of place for a holiday tune.

4. Jessica and Ashlee Simpson – “The Little Drummer Boy”
The Simpson sisters’ breathy vocals and over-the-top string arrangements make their version of this classic carol feel more melodramatic than heartfelt.

3. NewSong – “The Christmas Shoes”
This overly sentimental song tells the story of a boy trying to buy shoes for his dying mother. While it tries to tug at the heartstrings, it often feels manipulative rather than moving.

2. Elmo and Patsy – “Grandma Got Run Over by a Reindeer”
A darkly comedic Christmas song about an elderly woman’s untimely death might have been funny to some, but it often crosses the line into uncomfortable territory.

1. Alvin and the Chipmunks – “The Chipmunk Song (Christmas Don’t Be Late)”
The ultimate ear-splitting Christmas song, the high-pitched voices of Alvin, Simon, and Theodore make this track grating rather than joyful, leaving listeners wishing for silence.

These Christmas songs are certainly memorable, but not for the right reasons. You might find yourself reaching for the classic holiday hits instead!