A Tale Of Two Playlists, 9 Christmas Songs To Skip And 9 To Play On Repeat
December rolls around and suddenly every store, radio station, and coffee shop is blasting holiday tunes like there’s no tomorrow.
Some Christmas songs fill your heart with joy and make you want to sing along at the top of your lungs.
Others?
Well, they make you want to dive for the skip button faster than Rudolph on Christmas Eve.
Disclaimer: This article reflects subjective editorial opinions about Christmas songs and should not be interpreted as definitive fact or universal consensus.
1. Grandma Got Run Over by a Reindeer by Elmo and Patsy
Picture this: a family tragedy turned into a comedic country tune that somehow became a holiday staple.
Elmo and Patsy created this bizarre ballad back in 1979, and honestly, it’s been making people cringe ever since.
The song tells the story of a grandmother meeting her unfortunate end via reindeer collision on Christmas Eve, which is about as festive as a snowball to the face.
Sure, it’s supposed to be funny, but after hearing it for the millionth time, the joke wears thinner than cheap wrapping paper.
2. I Want a Hippopotamus for Christmas by Gayla Peevey
A ten-year-old girl’s voice demanding an actual hippopotamus for Christmas might sound adorable for about thirty seconds.
After that? It becomes the musical equivalent of nails on a chalkboard.
Gayla Peevey recorded this novelty number in 1953, and it’s been haunting holiday playlists ever since like a persistent ghost of Christmas annoying.
3. Dominick the Donkey by Lou Monte
Lou Monte brought us this Italian-American Christmas ditty in 1960, celebrating a donkey helping Santa reach children in Italy.
While the cultural nod is sweet, the “hee-haw” sound effects repeated throughout the song are anything but.
It’s like someone took a perfectly nice story and decided to add the most irritating animal noises possible every few seconds.
4. Wonderful Christmastime by Paul McCartney
Even Beatles legends can miss the mark sometimes, and this 1979 synth-heavy track proves it.
Paul McCartney created something that sounds more like a keyboard demo than an actual finished song.
The repetitive lyrics basically say “we’re having a wonderful Christmastime” about eight thousand times without adding much substance.
That electronic choir sound?
It hasn’t aged well, sounding more dated than your grandpa’s disco moves, and the whole thing feels like McCartney phoned it in between more important projects.
5. My Only Wish by Britney Spears
Britney Spears ventured into Christmas territory in 2000 with this forgettable pop tune that sounds like every other early-2000s bubblegum track.
The song lacks any distinctive holiday flavor beyond some sleigh bells thrown in the background as an afterthought.
It’s basically a generic love song that happens to mention Christmas once or twice, feeling more like a B-side than a genuine holiday classic.
While Britney’s vocals are fine, the song fails to capture any real Christmas magic, leaving listeners wondering why they’re not just playing her actual hits instead.
6. Christmas Shoes by NewSong
If you want to ugly-cry into your eggnog, this 2000 tear-jerker is your jam, but most people prefer joy during the holidays.
The song tries so hard to tug at your heartstrings that it ends up feeling manipulative rather than moving.
Instead of spreading Christmas cheer, it spreads Christmas depression faster than fruitcake spreads through office gift exchanges, making everyone uncomfortable and sad.
7. Little Drummer Boy by The Jackson 5
The Jackson 5’s take on this classic carol sounds like someone hit the fast-forward button and forgot to stop.
While their harmonies are undeniably talented, the frantic pace turns a gentle lullaby into an anxiety-inducing race to the finish line.
Pa-rum-pum-pum-pum gets old real quick when it’s delivered at warp speed with over-the-top vocal acrobatics.
Sometimes less is more, and this hyperactive version proves that even incredible singers can overcomplicate a simple, beautiful song into something that gives you holiday stress instead of peace.
8. Do They Know It’s Christmas by Band Aid
Band Aid gathered dozens of British and Irish musicians in 1984 to raise money for Ethiopian famine relief, which was genuinely noble.
However, the lyrics come across as pretty condescending and culturally tone-deaf by today’s standards.
Lines suggesting Africa has no snow or rain completely ignore the continent’s diverse climates and geography.
Plus, the overall vibe feels more like pity than solidarity, making listeners uncomfortable rather than inspired to help, and the song’s dated production screams 1980s in all the wrong ways.
9. Baby, It’s Cold Outside by Dean Martin
Dean Martin’s smooth vocals can’t save this 1949 duet from its seriously problematic lyrics that haven’t aged well at all.
What was once considered a playful back-and-forth now sounds more like someone ignoring repeated requests to leave.
Lines about “what’s in this drink” and persistent pressure despite clear refusals make modern listeners cringe.
Though the melody is catchy, the uncomfortable subtext overshadows everything else, making it a holiday skip for anyone who values consent and respecting boundaries in their Christmas music.
1. Christmas (Baby Please Come Home) by Darlene Love
Darlene Love’s powerhouse vocals turn longing into pure holiday gold on this 1963 Phil Spector production.
Her voice soars over the Wall of Sound arrangement like a shooting star across a winter sky, delivering genuine emotion without feeling manipulative.
The song captures that bittersweet feeling of missing someone special during the holidays, which honestly hits different than generic cheerful carols.
Every year when this plays, you can’t help but feel the raw passion in Love’s delivery, making it a timeless classic that deserves endless repeats throughout the season.
2. Have Yourself a Merry Little Christmas by Frank Sinatra
Ol’ Blue Eyes delivers this tender classic with such smoothness that it feels like wrapping yourself in a warm blanket by the fireplace.
Frank Sinatra’s 1957 version strikes the perfect balance between melancholy and hope, acknowledging that holidays can be complicated while still encouraging joy.
His impeccable phrasing and emotional control make every word feel personal, like he’s singing directly to you and only you.
3. Christmas Time Is Here by Vince Guaraldi Trio
If Christmas had an official soundtrack, this dreamy jazz piano piece from the 1965 Charlie Brown special would be it.
Vince Guaraldi created something magical that captures winter’s quiet beauty without needing flashy production or loud vocals.
The gentle piano melody combined with children’s choir voices creates an atmosphere so peaceful you can practically see snowflakes falling outside your window.
4. The Christmas Song (Chestnuts Roasting on an Open Fire) by Nat King Cole
Timeless Christmas elegance pours out of a 1946 recording shaped by a velvet-smooth vocal performance, with a level of sophistication that only Nat King Cole could deliver so effortlessly.
Every line paints a vivid picture of an idealized holiday scene, from roasting chestnuts to mistletoe and presents under the tree.
Cole’s warm delivery feels like receiving a hug from someone who genuinely cares about your happiness and wellbeing.
Decades later, this remains the gold standard for Christmas music.
5. White Christmas by Bing Crosby
Bing Crosby’s 1942 masterpiece became the best-selling single of all time for excellent reasons that still hold up today.
His rich baritone voice captures nostalgia and longing so perfectly that even people who’ve never seen snow feel homesick hearing it.
The song’s gentle simplicity allows listeners to project their own holiday memories and dreams onto it without forcing specific emotions.
6. Rockin’ Around the Christmas Tree by Brenda Lee
Recorded in 1958 by a thirteen-year-old performer, this rockabilly Christmas bop crackles with unstoppable energy that makes every moment feel joyful and alive, powered by Brenda Lee.
The upbeat tempo and catchy melody make it impossible to sit still, turning any gathering into an instant dance party.
Decades of holiday parties have proven this track’s staying power, making it perfect for anyone who wants their Christmas playlist to actually get people moving and grooving together.
7. A Holly Jolly Christmas by Burl Ives
A warm, storytelling voice evokes the feeling of a favorite uncle who always has time for a tale and a piece of candy, a comforting charm long associated with Burl Ives.
His cheerful 1964 recording radiates pure wholesome joy without a single trace of irony or manufactured emotion.
The song encourages friendly greetings, mistletoe kisses, and general merriment in the most genuine way imaginable.
8. It’s Beginning to Look a Lot Like Christmas by Perry Como
A laid-back 1951 recording captures that magical moment when holiday decorations begin appearing everywhere and anticipation quietly builds, a seasonal feeling perfectly embodied by Perry Como.
His relaxed vocal style makes the song feel effortless, like he’s casually observing the season’s arrival while sipping something warm.
The lyrics detail specific Christmas preparations from toys in stores to candy canes and silver lanes, creating vivid mental images.
9. All I Want for Christmas Is You by Mariah Carey
Mariah Carey didn’t just record a Christmas song in 1994, she created THE modern Christmas anthem that rules the season.
Her incredible vocal range and the song’s Phil Spector-inspired production combine to create pure holiday perfection in under four minutes.
The lyrics focus on love over material gifts, which feels refreshingly genuine in our consumer-obsessed culture.
Every December, this song dominates charts worldwide, proving that Carey’s masterpiece has achieved the rare status of becoming a legitimate instant classic that transcends generations and musical tastes completely.
