Even though some radio stations have been playing Christmas music since the end of Halloween, the first Saturday of December is a safe time to become entirely consumed by Christmas music. Christmas music can be surprisingly divisive; you either love it or hate it. As an exuberant member of the former, there’s no person on this site more qualified to rank the best music to listen to during the holiday season.
Christmas music is difficult to compose because it’s impossible to live up to the legends — Bing Crosby, Johnny Mathis and the like — but some modern musicians have mastered the craft better than others. I’ll grant you, some on this list aren’t exactly “modern,” but you should bear with me because you will not need to look any farther to find better Christmas music this holiday season.
15. ‘N Sync – Merry Christmas, Happy Holidays
You may be anti-boy band, but you cannot deny the late 90’s melody is a wonderful way to get in the spirit. If you can’t appreciate the piano, you can certainly appreciate a Gary Coleman cameo.
14. Ludacris — Ludachrismas
Even though Fred Claus was a terrible movie, at least it produced a high quality Christmas rap.
13. Chris Brown — This Christmas
Before he dabbled in domestic violence, Chris Brown brought soulful Christmas cheer. Don’t get this song confused with the movie he was in titled “This Christmas” that was garbage (I don’t know this with 100% certainty because I haven’t seen it, but if Chris Brown was acting one can only assume).
12. George Strait — Christmas Cookies
George Strait’s Christmas Collection is a holiday must, and this is the crown jewel. Strait keeps it simple, but comes with original material. It’s an honest song, because who other than George Strait would call sprinkles, “sprinkly things?” It’s also inspiring; if you never thought about 15 minutes of a kissin’ and a huggin’ in between cookie batches, you can thank Mr. Strait.
11. Trans-Siberian Orchestra — Carol of the Bells
Music without lyrics is rarely appreciated anymore, but this is one song everyone can enjoy.
10. Celine Dion — O Holy Night
This is a song where you want to hear somebody amazing belt out the chriscendo, making the peak of the song perfect. Celine does that and more with ‘O Holy Night.’
9. Alvin and the Chipmunks — Chritsmas Don’t Be Late
Alvin and the Chipmunks have returned in 3D, but nothing can beat the original. I didn’t realize the original was released in 1958, but since the Chipmunks cartoons didn’t hit the air waves until the 80’s, they can still fall under the “modern” umbrella.
8. Whitney Houston — Do You Hear What I Hear?
One of the best voices to ever grace this green Earth, Whitney Houston has to make the list at some point, and this song just isn’t the same sung by anyone else.
7. Run DMC — Christmas in Hollis
An innovative tune that is will forever be fun to “bump” to, Christmas in Hollis is the quintessential Christmas song because it combines the classics with modern mood. If “first Christmas rap song” didn’t eternally cement the song into American pop culture, it’s appearance in Die Hard certainly ensured that people will hear this song for years and years to come.
6. Faith Hill — Where are you Christmas?
The cartoon version of The Grinch That Stole Christmas was a already a must-see classic, yet Jim Carrey found a way to top it 15 years ago. Faith Hill’s song defined the movie’s theme against materialism during the holiday season.
5. Stevie Wonder — What Christmas Means to Me
The young Stevie Wonder can do nothing but make you happy, much like Buddy the Elf when he first entered Gimbel’s department store.
4. The Drifters — White Christmas
An oldie but a goodie, this one makes the “modern” list because it appeared in Home Alone 2, one of the best Christmas movies in the last 25 years. It’s also the foundation of one of my favorite stories from college. After a raucous night of celebrating the end of a semester, my friends and I broke out in song at the pavilion after closing time. We may or may not have attracted an audience, but regardless, it’s a memory I’ll never forget (even though I probably should have, if you catch my drift).
3. John Lennon — Happy Xmas
John Lennon’s writing is better than his singing, but the children in the background ensure a wholesome sound that will live on for generations.
2. Mariah Carey — All I want for Christmas is You
A perfect blend of beautiful voice, mixed with a Christmas classic to form a modern masterpiece. I know, it’s tough putting the young and beautiful Mariah second, but you’ll see my reasoning is sound.
1. Bruce Springsteen — Santa Claus is Coming to Town
Do I have a Bruce bias? No, my bias comes from Clarence’s saxophone. With Bruce’s energy and a Saxy Santa Claus, nothing in the world can get me more excited from Christmas.