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Writer's pictureBOOBEES Magazine

The Official Ranking of the Top Ten Holiday Songs of All Time, Ever

Updated: Oct 23

By: Emma Sikes





As an avid Christmas hater, I look down upon anyone humming, tapping or jingling their bells to Christmas music on or before Thanksgiving. Thirty-one days is plenty of time to enjoy all the season has to offer. That goes for decorations too, specifically the battery operated felt covered characters that sing at the press of a button. Keep those, wrapped in bubble wrap, in your red storage containers until Black Friday PLEASE. As a self-declared grinch, know that I will be harsh, but fair, in my ranking of the Top 10 Holiday Songs of all time.


I’ll start with my honorable mentions, Pentatonix, these harmonizing rascals don’t even need ‘stramnets to elicit tears! They do a gorgeous arrangement of “Silent Night” that I believe I’d be remiss if not to mention it (honorably). The acapella group has fantastic reimagined versions of gospel and classic Holiday favorites sure to make you weep/bang on your steering wheel along with the drums (oh wait, that's just the sounds they’re making with their mouths! #what?!) Next up, is “Mistletoe” by Justin Bieber, released in peak Belieber era (2011). This holiday pop song was the most requested song from my Instagram poll, as ultimately I am a people pleaser, here it stands. Lastly, a personal favorite, “Put One Foot In Front of The Other”, by Keenan Wynn and Mickey Rooney. The title may seem unrecognizable, but if you watched the 1970’s claymation classic “Santa Claus is Coming To Town'' every year like I did, you’ll love this joyful throwback. Get into horrible 70’s claymation, it's frightening in such a familiar way, you’ll love! 


Alright, now for the real list. Starting at the tenth spot, we have “Christmas Wrapping” by The Waitresses, released in 1981. An alternative, indie Christmas tune, ending with a last minute grocery run that reunites her and “the guy she's been chasing all year”. 


In the ninth spot is 1960’s classic, “What Are You Doing New Year's Eve”, sung by Ella Fitzgerald. A realistic question posed by a woman post cuffing season, “Are we still together, or am I looking for someone new to kiss on New Years Eve?” Relevant message, gorgeous orchestration, skipping right over the sappy Christmas cliches, what more could you want? 


Onto the eighth slot, “Happy Holidays/The Holiday Season” by Andy Williams. This classic upbeat tune is led by a crooner and backed with a meaty chorus. It has fun, and funky 60’s phrases like, “hoop-de-do” and “dickery dock”, making this a must listen this… “Holiday Season”. 


In the seventh spot is “Cool Yule” by the one and only Bette Midler. This song, originally sang by Louis Armstrong, satisfies your big band and innuendo cravings, alike. The album cover is a definite draw as well, It features Midler in a huge red feather wig for absolutely no reason. 


The sixth spot is “I Saw Mommy Kissing Santa Claus” by the Jackson 5. I don’t know about you, but I can forgive a lot (an off-putting premise of a child watching his mom have a makeout sesh with Santa) if it’s sung in five part harmony. This upbeat comedy song is beautiful and also dispels Santa's existence all together, good luck explaining this one to your kids! 


Number five, Kelly Clarkson’s “Underneath The Tree”, a pop-love song, with essential K. Clarkson belting, it’s fun, and it’s flirty, nuff said. 


In the fourth spot is “Hanukkah, Oh, Hanukkah” by Barenaked Ladies, a bluegrass take on a Hanukkah classic.


 In the third spot, is Easy E’s “Merry Muthaf***in X-mas”, it’s exactly what you think it would be, a good palate cleanser from the regular grocery store friendly Holiday tunes. 


The second best Holiday song according to me, is “Christmas (Baby Please Come Home)” by Darlene Love, this song makes me feel warm and cozy on the  inside, the perfect ending to any Christmas movie. 


And now, the moment you’ve all been waiting for, the absolute best Holiday song of all time, so far, is “This Christmas” by Donny Hathaway. Along with being a soulful, and catchy big band extravaganza, it also brought us a top tier Patti Labelle meme. Featuring her, singing at the National Christmas Tree Lighting, not knowing the words, yelling at a cue card girl, and screaming “Where are my background singers?!” It’s iconic people, look it up!

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