The Best And Worst Holiday Songs Of All Time

What would the holiday season be without so-called “Christmas music”? (A lot quieter, definitely, but the holiday season would lose a bit of the warmth.)

Christmas is nearly upon us, so it’s the perfect time crank up the holiday tunes. From old classics like Bing Crosby’s “White Christmas” to The Beach Boys’ “Little Saint Nick”, we’ve got you covered with our lists of best and worst festive tunes.

READ MORE: How to re-gift thoughtfully this holiday season

Here are 10 of our favourite worst holiday songs. (Check out our Spotify playlists below each list.)

Top 10 Worst Holiday Songs

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

Alvin just wants a hula hoop, and many people never want to hear this song again. What can be worse than singing in chipmunk voices? Oh right, an entire recording of singing in chipmunk voices. Sometimes multiple chipmunks.

2. Paul McCartney and Wings – “Wonderful Christmas Time”

Every December, shockingly, this song is overplayed so we can all have the “simply having” part stuck in our heads all day. “Wonderful Christmas Time” is full of sounds from a creative keyboard that will be sure to drive you crazy.

3. David Hasselhoff – “The Christmas Song”

This Christmas medley starts off with “Jingle Bells” before moving into “Chestnuts”. The kids in this music video don’t seem to match the same enthusiasm that Hasselhoff brings to the screen in this holiday video. Can’t say we blame them.

4. Elmo & Patsy – “Grandma Got Run Over By A Reindeer”

Arguably one of the most annoying holiday songs out there, and we’ve still yet to hear of anyone’s grandmother getting run over by a reindeer.

5. Destiny’s Child – “8 Days of Christmas”

Instead of 12 days of Christmas, Destiny’s Child only had time for 8.

6. *NSYNC – “Merry Christmas, Happy Holidays”

This boy band’s use of the green screen for the “action” shots of the group travelling the world on their sleigh really puts a timestamp on this gem. You’re not really riding in that sleigh, guys. We know.

7. Bob Dylan – “It Must Be Santa”

This upbeat, accordion-driven Christmas melody is just one of many holiday songs on Dylan’s 2009 holiday album, “Christmas in the Heart”. Correction: Nobel Prize-winning Dylan.

8. Justin Bieber – “Mistletoe”

Bieber is pledging to be under the mistletoe with his “shawty.” Nothing more to hear here.

9. New Kids on the Block – “Funky, Funky Xmas”

This song includes the phrase “Yo, MC Santa, you didn’t know my boy Donnie could play percussion, did you?” Former NKOTBer Donnie Wahlberg penned this holiday tune.

10. DMX – “Rudolph The Red-Nosed Reindeer”

Rapper DMX puts his own a capella twist on this classic holiday melody. We’re not sure why.

READ MORE: 13 holiday movies that will put you in a festive mood

Holiday music gets a bad reputation, maybe because it takes over our radio and commercial spaces during December; but not all festive tracks are considered “the worst.”

Here are some of the best Christmas anthems, in no particular order.

Top 10 Best Holiday Songs

1. Mariah Carey – “All I Want For Christmas Is You”

This 1994 Christmas classic is catchier than a cold in the winter. With everything from the sleigh bells to the pop hooks, you’ll surely be singing along.

2. Bruce Springsteen — “Santa Claus Is Comin’ to Town”

Springsteen will perform this holiday classic live if he has concerts around the holiday season. He just performed it in May of this year (strangely), when he brought a fan dressed as Santa Claus on stage on his UK tour’s opening night.

3. Bing Crosby – “White Christmas”

Crosby’s version of “White Christmas”, written by Irving Berlin, remains the best-selling recording of all time with The Guinness Book of World Records reporting worldwide sales of over 50 million singles. And yes, that’s best-selling recording of all time, not best-selling Christmas recording.

4. Stevie Wonder – “Someday At Christmas”

In 2015, Apple’s annual holiday TV commercial featured musical legend Wonder singing a duet of his classic Christmas hit from 1967, “Someday At Christmas”, with singer Andra Day. It doesn’t matter if Wonder is just shilling for Apple, the song is beautiful.

5. The Jackson 5 — “I Saw Mommy Kissing Santa Claus”

Many of the tracks from “The Jackson 5 Christmas Album” are played in heavy rotation on radio stations during the Christmas season and are frequently requested by its listeners. Who can blame them?

6. Darlene Love – “Christmas (Baby Please Come Home)”

Love sang the original version of this Christmas classic, but many others have created covers of the track including Mariah Carey, Hanson and U2. The original song was used in the movies “Gremlins” (1984), “Goodfellas” (1990), “Bad Santa” (2003), “Christmas with the Kranks” (2004), and “The Perks of Being a Wallflower” (2012). Wow.

7. Wham! — “Last Christmas”

Many say this four-and-a-half minute holiday ballad isn’t about Christmas at all. But the song lyrics talk about “giving” away a heart, which isn’t just a declaration of affection. Sadly, going by the lyrics, it sounds like the gift heart has been re-gifted.

8. The Beach Boys – “Little Saint Nick”

This peppy jingle offers a humourous, hip take on Kris Kringle, as it uses a candy-apple red hot rod as Santa’s sled whipping through the snow.

9. Michael Bublé – “It’s Beginning To Look A Lot Like Christmas”

Bublé covered this song and released it on his holiday album, “Christmas”Crosby also recorded a version of this song on October 1, 1951, which was also widely played. Regardless of the singer, this tune is widely beloved.

10. Run DMC – “Christmas in Hollis”

This is one of rap’s first Christmas songs, a tribute to the group’s hometown in Queens. It originally appeared alongside Christmas songs by U2, Bon Jovi and Sting on a 1987 charity CD, “A Very Special Christmas“, which benefited The Special Olympics.

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