OnTheFlipsideMusic's 25 Days of Christmas Playlist
By Jessica Klausing
Merry Christmas!
It’s time to deck the halls again, and what better way to get into the holiday spirit than with music! Whether you prefer the good old fashioned classics or the modern hits, we’ve curated a holiday playlist that offers a little something for everyone.
In no particular order here are our 25 Days of Christmas playlist:
“A Marshmallow World” - Dean Martin
Even though the song about the winter landscape, it’s still considered one of the Christmas classics. The lyrics compare the snowfall to marshmallows covering the ground along with other dessert-like metaphors making this a holiday comfort song.
2. “All I Want for Christmas is You” - Mariah Carey
Holiday retail workers either love this song or loathe it with a passion! It’s a cheerful melody, but Mariah’s pitch perfect high notes are the real stand out on this track.
3. “Merry Christmas, Happy Holidays” - *NSYNC
This is the quintessential feel-good modern day Christmas song. With catchy bubblegum pop lyrics like “It’s a wonderful feeling/feel the love in the room/from the floor to the ceiling,” it’s guaranteed to put any Scrooge in the Christmas spirit.
4. “Rockin’ Around the Christmas Tree” - Brenda Lee
This classic is a must for any Christmas party playlist! The lyrics and melody are catchy, but the best part is when the beat stops on “Voices singing, let’s be jolly/Deck the halls with boughs of holly.”
5. “A Holly Jolly Christmas” - Alan Jackson
This is another popular Christmas classic. Alan Jackson’s honky tonk rendition gives it a small town country feel.
6. “This Christmas” - Joe
Grammy-nominated singer-songwriter Joe delivers with this sultry, R&B melodic Christmas hit. It’s another highly recommended one to liven up the holiday party.
7. “Sleigh Ride” - TLC
TLC took a classic and re-worked it into a fun-filled festive R&B ditty with new lyrical hooks, playful banter, and of course, an epic rap from Lisa “Left Eye” Lopes.
8. “Have Yourself a Merry Little Christmas” - Michael Bublé
Michael Bublé’s warm vocals give all the cozy vibes. This is one to listen to snuggled up by the fireplace with a cup of hot cocoa.
9. “It’s Beginning to Look a Lot Like Christmas” - Bing Crosby
It’s not a true Christmas playlist without Bing Crosby. While this is another popular classic covered by many artists, there’s just something special and nostalgic about listening to Bing regale about a town getting ready for Christmas.
10. “O Holy Night” - Carrie Underwood
A beautiful Christmas hymn performed by one of the most iconic voices in Country music.
11. “Santa Claus is Comin’ to Town” - Bruce Springsteen
The Boss captures the rock ‘n roll spirit with this energetic rollicking rendition.
12. “Blue Christmas” - Elvis Presley
Christmas music and The King of Rock ‘N Roll go together like peanut butter and bananas. Elvis will tug on your heartstrings with this sentimental ballad. However, if you’re looking for a good laugh, the Porky Pig version is definitely worth a listen!
13. “My Only Wish (This Year)” - Britney Spears
Britney charms her way into our hearts with this sweet song that’s filled with catchy wholesome lyrics and a bouncy pop melody.
14. “Christmas Time” - Backstreet Boys
Perhaps the most gorgeous harmonies featured on a modern pop Christmas song.
15. “Wonderful Christmastime” - Paul McCartney
Paul’s cheery spirit is quite infectious on this one! It’s hard to resist singing and bouncing along to the beat.
16. “Happy Xmas (War is Over)” - John Lennon, Yoko Ono, and The Plastic Ono Band
Recorded as a protest against the Vietnam War, “Happy Xmas (War is Over)” has become a Christmas song standard.
17. “Winter Wonderland” - Alexander O’Neal
Reaching #54 on the Top R&B/Hip Hop Albums, Alexander O’ Neal dazzles with his soulful rendition of this timeless classic.
18. “Christmas Time is Here” - Vince Guaraldi Trio
Famously known as the opening theme in A Charlie Brown Christmas, this comforting classic brings a smile to all ages.
19. “Zat You, Santa Claus?” - Louis Armstrong
An underrated swingin’ holiday tune with all the Creole Jazz goodness.
20. “Mary, Did You Know?” - CeeLo Green
This one is a real tearjerker! CeeLo delivers a beautiful, heartfelt performance that embodies the true meaning of Christmas.
21. “Run Rudolph Run” - Chuck Berry
A fun, high energy performance by the Father of Rock ‘N Roll.
22. “Please Come Home for Christmas” - The Eagles
Only The Eagles can take a bittersweet song about spending Christmas alone and turn it into a beautiful rockin’ masterpiece with a wailing guitar.
23. “Christmas in Dixie” - Alabama
This country song is a celebration of Christmas in the southern American states.
24. “Step Into Christmas” - Elton John
Elton brings the Christmas spirit with ringing bells, angelic choirs, and lots of high energy!
25. “Christmas Vacation” - Mavis Staples
As featured on National Lampoon’s Christmas Vacation, it’s a holiday banger that will easily get stuck in your head.
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