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1.

“Underneath the Tree” — Kelly Clarkson

Kelly Clarkson singing in a formal red dress as snow falls around her


Sony / Via youtube.com

Honestly one of the most underrated holiday songs. Even if you rate it, it’s still underrated.

2.

“Christmas (Baby Please Come Home)” by Darlene Love

Darlene Love sings in front of a microphone wearing a red and white patterned top


ABC / Via youtube.com

Love’s “All Alone On Christmas” deserves a shout out, but it’s just edged out by this absolute icon.

3.

“Ribbons and Bows” by Kacey Musgraves

Kacey Musgraves dances in front of a cheering crowd in a room decorated for Christmas


Amazon Prime

Kacey Musgraves has some great holiday music, but this up-tempo bop is the best. There’s nothing super revelatory about it; it’s just pure FUN, and who doesn’t need that at the holidays?

4.

“A Christmas Duel” by The Hives and Cyndi Lauper

Cover of the single for "A Christmas Duel" by The Hives and Cydni Lauper


The Orchard / Via youtube.com

What’s more festive than people being hurling insults at each other and begrudgingly spending time together? *Cough*

5.

“Christmas in Hollis” by Run DMC

Run DMC perform in a room decorated for Christmas


Sony / Via youtube.com

It is impossible to listen to this song and not be in a good mood.

6.

“Don’t Shoot Me Santa” by The Killers

Brandon Flowers sings in the backseat of a convertible with tinsel wrapped around his body


UMG / Via youtube.com

A frankly ridiculous song, and I mean that in the best possible way.

7.

“Fairytale of New York” by The Pogues

Black and White still from the "Fairytale of New York" music video; Shane MacGowan  sings at at a piano, wearing sunglasses and a suit


Warner Music UK / Via youtube.com

This song is not without controversy, with a lot of pushback over offensive words used in the lyrics. But there’s no denying the huge impact the song has had on the holidays. In the UK, it even beats out Mariah Carey for the most-played modern Christmas tune.

8.

“White Wine in the Sun” by Tim Minchin

Time Minchin smiles while singing into a microphone


CBS / Via youtube.com

This song speaks directly to the skeptical, secular millennial holiday spirit, while also delivering one hell of a love song to his own baby girl. He also evokes distinctly Australian imagery that is a stark contrast to traditional white Christmas vibes.

9.

“Let It Snow” by Boyz II Men

Boyz II Men wear matching Christmas cardigans and sing while sitting around a table in front of a bookshelf


Universal Music / Via youtube.com

So much ’90s nostalgia. Remember Boyz II Men performing it on The Fresh Prince of Bel-Air? Incredible

10.

“Someday at Christmas” by Stevie Wonder

Stevie Wonder sits in a room decorated for Christmas


Sony / Via youtube.com

Released in response to the Vietnam War, “Someday at Christmas” is a wistful song about wanting peace, happiness and equality on Earth.

11.

“That’s Christmas To Me” by Pentatonix

Pentatonix sit in a room decorated for Christmas, with a tree and presents off to the side


Sony / Via youtube.com

Pentatonix have so many excellent covers of classic holiday songs, but this original is lovely too.

12.

“Christmas Time (Don’t Let The Bells End)” by The Darkness

Justin Hawks sings in front of a fire


WMG / Via youtube.com

No offence to “All I Want For Christmas Is You”, but this is the holiday song that is actually the most fun to sing along to.

13.

“California Christmastime” by the Crazy Ex-Girlfriend cast

Darryl and Carol from Crazy Ex-Girlfriend wear Christmas sweaters and look into the camera while a woman with curly hair and a henna tattoo on her chest looks down


The CW / Via youtu.be

Like every Crazy Ex-Girlfriend song, “California Christmastime” is both hilarious and catchy as hell.

14.

“Santa Tell Me” by Ariana Grande

Ariana Grande dances in a dark room while wearing a Christmas sweater and sparkly reindeer antlers


Republic / Via youtu.be

Ariana brings her own flavor to the classic Christmas genre: asking Santa to solve all your romantic troubles.

15.

“Christmas in Harlem” by Kanye West featuring Cyhi Da Prynce and Teyana Taylor

Single cover of "Christmas in Harlem" featuring the text: "Christmas in Harlem" Kanye West, Cyhi Da Prynce, Teyana Taylor


Universal / Via youtube.com

Kanye West might not be the first artist you think of in association with Christmas, but this is an underrated addition to the non-traditional canon.

16.

“Santa Baby” by Eartha Kitt

Earth Kitt stands in front of a red striped wall wrapped in fur with her shoulders exposed


VCI / Via youtube.com

The holidays deserve some sexy songs too. And this is the sexiest.

17.

“Blue Christmas” by Elvis Presley

A sweaty Elvis Presley wears a black leather jacket and sings into a microphone


Sony / Via youtube.com

Another sexy Christmas song, but this one is also kinda mopey. Because sad and horny is the vibe of the season.

18.

“Please Come Home For Christmas” by Eagles

Single cover for "Please Come Home For Christmas" by Eagles featuring a group of people sitting around a pool in swimsuits


Mercury / Via youtube.com

There are a few significant covers of this song, but this is the most iconic of them all.

19.

“Have Yourself A Merry Little Christmas” by Judy Garland

Close up of Judy Garland in Meet Me In St Louis


Warner Bros / Via youtube.com

Written for Meet Me In St Louis (a fantastic movie), this song has transcended its origins to become a Christmas classic. But Judy Garland’s wistful take on it is still the definitive one.

20.

“2000 Miles” by The Pretenders

Chriss Hynde wearing a dark bonnet with fake snow on her head and shoulders


youtube.com

With themes of yearning and loss, it captures the way the holiday season makes you miss people in a very particular way.

21.

“How To Make Gravy” by Paul Kelly

Paul Kelly playing a guitar and singing into a microphone while standing on a rooftop, with a guitarist standing behind him


UMG

“How To Make Gravy” tells a cathartic story that captures the feeling of being separated from your family and missing Christmas altogether.

22.

“River” by Joni Mitchell

Black and white image of Joni Mitchell ice skating


Warner / Via youtube.com

There have been many amazing covers of this heartwrenching song, but nothing beats Joni.

23.

“Mistletoe” by Justin Bieber

Justin Bieber wearing a jacket and standing in front of a lantern in the snow


UMG / Via youtube.com

It’s a bop and if you deny it you’re just deluding yourself.

24.

“Last Christmas” by Wham!

George Michael stares intently at someone over a wine glass; in front of him a man and a woman carry on a conversation


Sony / Via youtube.com

Not quite the greatest holiday song of all time (that title is reserved for another, which I’ll get to, don’t worry), but it’s up there.

25.

“Merry Christmas Baby” by Otis Redding

Record cover of "Merry Christmas Baby" by Otis Redding, featuring an image of Otis Redding in the middle of a star


Rhino

Many have tried, but no one has ever done this song as well as Otis Redding.

26.

“Snowman” by Sia

Claymation image of a girl with two snowmen


WMG / Via youtube.com

A sweet little ditty that’s elevated by Sia’s soulful voice. Sia’s entire holiday album is wonderful.

27.

“Baby, It’s Cold Outside” by the Glee cast

Kurt and Blaine from Glee wearing school uniforms and singing together


Fox / Via youtube.com

There’s a lot of discourse around this song, but it’s damn catchy, and this performance by Kurt and Blaine on Glee is an utter delight.

28.

“What Christmas Means To Me” by John Legend and Stevie Wonder

Cover of "A Legendary Christmas" album by John Legend featuring John Legend wearing a Santa hat


Columbia / Via youtube.com

John Legend’s holiday album is a wonderful mix of classics and original songs, but it’s this cover/duet with Stevie Wonder that is the ultimate gift.

29.

“All I Want For Christmas Is You” by Mariah Carey

Mariah Carey wears a red outfit with fluffy white trim and bends down next to a reindeer


Sony / Via youtube.com

THE QUEEN, UNDEFEATED, CAN NEVER BE TOPPED.

Like this list? Here’s a Spotify playlist for your listening pleasure:


embed.spotify.com



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