Top 5 Holiday Songs to Deck the Halls To

It’s the holiday season! The season of giving! The festival of lights! Spreading joy to people young and old! (Can you tell I’m excited?)

I flat out love the holidays. Picking out the perfect gifts for the people I love, putting lights up around my room, decking the halls with boughs of holly… it puts me in such a good mood! This year is no different, and I’m even more excited than usual.


Well, this is the first Christmas that we’re celebrating with my sister-in-law! (Technically this is also first Christmas that I have a sister-in-law, but that’s beside the point.) She and my brother opted to stay local for the holidays this year, and I’m stoked to have them around. Also, the boyfriend is coming! He’s dreamt about spending Christmas in New York for years, and I’m beyond happy that I get to be part of his dream come true.

This is gonna be good.

Christmas has always been a big deal for my family. It’s the one holiday where we have pretty tried and true traditions that essentially span the entire month of December. We put our 49-year-old synthetic tree up really early— usually over Thanksgiving weekend— while listening to Christmas classics on vinyl, with Bing Crosby, Rosemary Clooney, and The Carpenters being staples. My mom and I have cookie baking days, keeping some for ourselves, eating all the “broken" ones, and gifting the rest to friends and family. I pull out the cinnamon scented candles and my Santa hat sits perched on the corner of my closet door all month.

And then, there’s the food. Christmas Eve is everything Italian, and we get as close as possible to keep up the tradition of the Italian feast of the seven fishes (it’s not the same since my grandma passed, but still delish.) More recently, we’ve been getting invited to my best friend’s house to have Christmas Eve dinner with her and her extended family, and I love being part of their tradition, too.

Christmas morning includes opening gifts in our pajamas and eating angel food cake for breakfast. We switch to Polish food for Christmas Day, like kielbasa and potato salad, and lots of other yummy dishes that my Polish family would eat during the holidays.

Now, do I get excited seeing beautifully lit streets as I’m driving home? Yes. Does the kid in me love watching the old stop-motion Christmas specials like “The Year Without A Santa Claus” and “Rudolph’s Shiny New Year?” Of course. Do I love seeing piles of gifts under the tree on Christmas morning? No doubt. Will I jam out to Christmas carols on the radio for four weeks straight? You’re dang right I will.

But what I’ve really started to learn and appreciate as I’ve gotten a little older is how special it is to get to celebrate with the people you love year after year. I have a relatively small family, and for years our holiday get-togethers have been really small. I’ve complained, felt upset by how quiet the days were, and wished that I had cousins and extended family nearby to celebrate with. But, appreciating togetherness doesn’t only happen when your guest list is in the double digits.

Six months ago, I was prepared to accept a simple, quiet Christmas Day with just me, my parents and my grandpa. Now, I’m thrilled by the unexpected twist of having my brother, sister-in-law, boyfriend, and of course my puppy nephew at our house to spend Christmas together. I’m excited to share our family traditions, and even more excited to have another year to keep those traditions alive.

Having a family and friends to celebrate with— no matter how many or how few people it may be— is a huge blessing, one that I think many of us take for granted. It actually makes me a little choked up thinking about how wonderful this Christmas is going to be in spending it with all of the people I love the most. That’s my kind of Christmas.

My nod to Bing Crosby is not to go unnoticed, and I’m sure it’s no shock that a huge part of what gets me in the holiday spirit is music. This week I'm doing a combo "Top 5" and "Songs To… Deck the Halls To," because I think the season of giving calls for an extra sprinkling of holiday cheer. I came up with an extensive list of my faves in the blink of an eye, and you guys had so many songs that you play on loop during the holidays, too many to include in one article! But fear not, and instead check out our YouTube channel for the full playlist! 

Your Picks:

℗ 1998 Trans Continental Records, Inc.

“Merry Christmas, Happy Holidays”

Please enjoy the ridiculous and adorable video for this quintessential 90’s Christmas jam.


℗ 1996 Warner Bros. Records Inc. for the U.S. and WEA International Inc. for the world outside the U.S.

"The Hannukah Song"
Adam Sandler

Christmas isn't the only winter holiday!


℗ 1996 The Verve Music Group, a Division of UMG Recordings, Inc.

“Baby It’s Cold Outside”
Ella Fitzgerald and Louis Jordan

Cute, cheeky, charming; perfect for the cold winter weather.


℗ 2016 Atlantic Recording Corporation for the United States and WEA International Inc. for the world outside of the United States. A Warner Music Group Company

Mary Did You Know?”
Straight No Chaser

A beautiful, haunting melody sung in perfect harmony.


℗ Compilation 2012 Capitol Records, LLC. All rights reserved.

“The Chipmunk Song (Christmas Don’t Be Late)”
Alvin and the Chipmunks

So silly, but something about it makes me smile.


My Top 5:

℗ Originally Released 1963 Sony Music Entertainment Inc.

“Most Wonderful Time Of The Year”
Andy Williams

(My secret crush on Andy Williams revealed here.)


℗ 2009 Phil Spector Records, Inc. Under exclusive license to EMI Blackwood Music Inc./Sony Music Entertainment

“Sleigh Ride”
The Ronettes

The jing-a-lings are infectious, what can I say?


℗ This compilation (P) 2014 Sony Music Entertainment

“It’s Beginning To Look A Lot Like Christmas”
Perry Como


Makes me want to casually stroll down the street, swinging around lamp posts and sipping cocoa.


℗ Originally released 1966. All rights reserved by The Dean Martin Family Trust

“Let It Snow! Let It Snow! Let It Snow!”
Dean Martin

See above fantasy, add a beautiful, delicate snowfall.


℗ 2004 Reprise Records for the U.S. and WEA International Inc. for the world outside the U.S.

Josh Groban

Polar Express makes me feel all the holiday feels.


Share more of your favorite holiday music in The Whatismyhealth Community group, or in the comments at the bottom of the page.

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