Our top holiday videos from the past and present!

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The most wonderful time of the year is back again, and it’s just around the corner. The lead-up to the holidays always seems to be filled with stress, but once it’s here, we all go back to being little kids as we enjoy the cheer that comes this time of year! With the holiday season comes the festive sing-along songs to get us in the spirit. Some songs are as old as the celebrations themselves, and some are brand new but have become modern classics. To help get you into the holiday spirit, we will be sharing some of our favorite past and present holiday videos.

This year’s top holiday videos:


“O Holy Night” by Grey DeLisle

No Holiday playlist is complete without some beautiful classics, and we’re starting ours with voice-over actress Grey DeLisle and her beautiful rendition of “O Holy Night.” Much like the song, the video is classic but elegant and full of holiday cheer. The video clips transform from color to black and white as she takes us into the studio for her recording session. This sophisticated but straightforward and beautiful video is exactly what we need to start getting into the holiday spirit.



“Christmas Day In America” by Tealand Smith

Next up on our list is Tealand Smith with his “Christmas Day In America” video. This video is all things merry and bright, which is exactly what you want for a holiday video. The video starts with the classic image of kids waking up mom and dad on Christmas morning. Then, they’re sitting around a beautiful Christmas tree as presents are ripped open with excitement. It comes to an end with a big family feast of good food and even better company. This year, everyone has been trying to find their way back to normalcy -and this video definitely helps us feel that way.



“The Covid 19 Christmas Song” by David King Jones

This next video also comes from 2020 in more ways than one. David King Jones’ “The Covid 19 Christmas Song” gets a little more realistic about the world right now and what it means for this holiday season. For this video, David is center stage in his own green screen world. Nostalgic clips of kids sleigh riding and the cramped malls flash by just to be interrupted by Santa disinfecting carts and not using cash in stores. As much as we would like things to go back to normal, we’re just not there yet, and Christmas, like everything else, will be looking different this year. This video is an important reminder to wear your masks, stay socially distanced, and limit the festive gatherings this year.



Some of our favorite holiday videos from the past:

“Santa Bring My Baby Back to Me” by Brynn Stanley

Brynn Stanley’s cover of “Santa Bring My Baby Back to Me” is a blast from the (recent) past. Brynn’s 2019 version of the Elvis original has just as much sparkle and soul as the King’s. The video looks like something straight out of a 1950s suburb with polka dots galore and a retro-inspired house. While waiting impatiently for her man to arrive, Brynn tries to keep herself busy by baking cookies and decorating the Christmas tree. Her holiday spirit is just about diminished until he comes home. After that, it’s celebrations galore. This is the perfect song to have playing while baking some cookies and getting some holiday chores done.


“She’s A Ho Ho Ho Merry Christmas” by Patent Pending

With this next video, we’re going back to November 2008 with Patent Pending and their “She’s A Ho Ho Ho Merry Christmas” video. This video is just as festive as it is sarcastic, and that’s just how the band wanted it. One thing for sure, you do not have to guess what this song is about, as it’s right in the title. The song is about a woman who sleeps around and uses the holiday season as a cover. The video takes place at a holiday party where a beautiful woman is flirting with none other than Santa Claus. All while the band performs in a snow globe with raining confetti. Eventually, the walls got torn down, and the festivities commence. It’s everything we love about pop-punk music and Christmas all mashed into one.


“We’re Going Caroling” by Dick Van Dyke & Jane Lynch

The next video on our list is a mix of old, classic Christmas and new, modern Christmas in the most amazing way. The “We’re Going Caroling” video from Jane Lynch and the legendary Dick Van Dyke, released in 2017, is a masterpiece of classic old-sounding Christmas music with a fresh new spin on it. The clip shows the two singing legends dancing and prancing around an old microphone. While they share with us their plan for caroling, the plain white backdrop suddenly starts to morph into snowflakes. The powdery snow swirls around them while they dance, sing, and even play some horns. There’s so much holiday joy and cheer in this video, so beware: it’s extremely contagious.



“Christmas Cookie Blues” by Broke Royals

This video is dedicated to everyone with a sweet tooth. Broke Royals released their “Christmas Cookie Blues” video in 2018. For this video, the boys are dressed in their best holiday suits as they sing around the decorated Christmas tree. As they’re baking cookies upon cookies, they dedicate the song to an ex-lover, reminiscing about the good times they’ve had during past holiday seasons. The cookies are baked and decorated just to be devoured by the end of the video. Not only will the video help you reminisce, but it will also make you want to bake as many cookies as possible.



“Merry Christmas Baby” & “First Thing on My Christmas List” by The Imaginaries

The last two videos on our holiday list come from our favorite couple, The Imaginaries. Every year Maggie McClure and Shane Henry release holiday music, and they can be heard just about everywhere Christmas music is played. The “Merry Christmas, Baby” video is a fun behind-the-scenes clip of the recording process and all the fun they have in the studio. The love has never been stronger between these two, and you can see it from a mile away. The video wouldn’t be complete without their furry four-legged friend. This bonus clip for “First Thing on My Christmas List” will definitely get you ready for the holidays. Looking for the perfect tree, decorating the house, and sitting by the fireplace with a mug of hot chocolate. These are two holiday originals that are sure to be holiday classics in no time.




Written by HIP Intern Rebecca Karaman.