The Top 20 Holiday Songs Of All Time

(The following is an unedited and extended version of an article that ran in the papers I work for. If you’d like to read that abridged version, go here. Otherwise, enjoy the following kilo of uncut Colombian holiday cheer.

Need a holiday party playlist in a pinch? Good news: After literally thousands of hours of research, yours truly determined the top 20 holiday songs of all time then ranked them using a groundbreaking harmonic algorithm…Okay, these are based solely on my opinion, but I think you’ll like them.

20. “The Christmas Shoes” by NewSong – Just kidding. This is tied with “Mad World” by Gary Jules as the most depressing song of all time and it belongs nowhere near a party unless you are subtlety trying to get people to leave, or cry. What the hell were the sociopaths of NewSong thinking when they put together the lyrics to this song?

-“Hey I think I just wrote this really beautiful Christmas song!”
-“Awesome, what’s it about?”
-“This little kid whose mom’s about to die on Christmas Eve.”
-“Wait, what?”
-“Yeah yeah, and he’s at a store buying her shoes.”
“Why wouldn’t he be at home? If anything, she needs shoes less than just about anyone on the planet.”
-“No, they’re for Jesus.”
“Oh”
-“But he can’t afford them.”
“Jesus?”
-“Her son.”
“That’s the most depressing thing I’ve ever heard.”
-“Yeah but then I come in and buy them for him, and then I realize that he had REALLY been sent by God the whole time.”
“Jesus?
-“No, the son.”
-So the Mom was never actually sick?”
-“What? No she’s dead.”
-“
Wow. Well at least she got new shoes.”
-“It was never about the shoes.
-“Oh. What’s the name of the song?
-“Christmas Shoes”

20. “We Need a Little Christmas” by The Muppets– From the underrated classic, A Muppet Family Christmas. Listen to this song and try not to smile. Seriously, try it. You can’t.

19. “Holly Jolly Christmas” by Burl Ives– Did you know Burl Ives is white? I have no idea why I thought he was black all these years but I seem to preemptively assume people’s race all the time. I thought Robert Griffin was white until like eight weeks into his last season at Baylor when I finally saw him and realized that he was, in fact, decidely nonwhite. In my defense, Rob Parker still hasn’t made that revelation just yet. This has absolutely nothing to do with Christmas, does it?

18. “God Rest Ye Merry Gentlemen” by Mannheim Steamroller– Listening to this song, you may think to yourself, “What is a mannheim steamroller and what does construction equipment have to do with Christmas?”, “What instruments am I listening to?”, “Are you sure this isn’t Trans-Siberian Orchestra?” All valid questions, still a great song.

17. “Jingle Bell Rock” by Bobby Helms– Nothing about bells screams “rock,” and yet Bobby Helms convinced America that jingle bell rock was something that could exist in nature, so credit Helms with paving the way for future generations to make literally anything rock- jail houses, planets, even crocodiles. Bobby Helms was a pioneer and Jingle Bells was his Plymouth Rock.

16. “Santa Claus is Coming to Town” by Bruce Springsteen– Even Springsteen recognizes that come Christmas Time, Santa Claus is The Boss. Bruce provides an excellent rock n’ roll tune-up on the tale of Santa and his E-Street Reindeer.

15. “Oh Holy Night” by Luciano Pavarotti– It’s basically everything that “Christmas Shoes” was going for, only successful.

14. “Sleigh Ride” by Johnny Mathis– Like Burl Ives, Mathis has a voice that instantly evokes the Christmas spirit. Whether you’re hanging ornaments on the tree or storming Toys R’ Us at 5 a.m. to viciously battle for the last Furby, this cheerful tune brightens any holiday tradition.

13. “Up on the House Top” by Jackson 5 Written in 1864, by Benjamin Hanby, it is believed that this song was the first to put forth the idea that Santa and his reindeer landed on the roof of homes. It thankfully supplanted the 1863 holiday hits, “In through the Crawlspace” and “Santa’s on the Dumbwaiter Again.”

12. “I Saw Mommy Kissing Santa Claus” by The Ronettes– The lyrics tell the rather dark tale of a child seeing Mom ostensibly cheating on Dad with a magical, obese man who snuck into the house. This song is proof that Motown can make absolutely anything sound good.

11. “Let It Snow!” by Dean Martin– Only the Rat Pack could turn an ominous weather forecast into a legendary love song. The solution to global warming is employing more meteorologists who can croon.

10. “Rockin’ Around the Christmas Tree” by Brenda Lee– What exactly is the “new old-fashioned way” to dance, besides a paradox? Is it a new interpretation of an old dance, like adding a hip new flair to the Charleston? Or is it whatever dance has most recently stopped being popular? If people start doing the Dougie around your Christmas tree, you’ll know it’s the latter.

9. “White Christmas” by The Drifters– The original Bing Crosby version may be a classic, but The Drifters’ cover featured prominently in the Home Alone scene when Kevin McCallister lip-syncs  in the mirror before dousing his face with aftershave. Advantage: Drifters.

8. “The Christmas Song (Chestnuts Roasting on an Open Fire)” by Nat King Cole– Perhaps the most iconic holiday song ever written, it was ironically penned by Mel Tormé and Bob Wells in the middle of a mid-summer heat wave in 1944 as a way to try and stay cool. Huh.

7.  “You’re a Mean One, Mr. Grinch” by Thurl Ravenscroft– Name another Christmas song that can get away with containing lyrics like, “Your soul is an appalling dump heap overflowing with the most disgraceful assortment of rubbish imaginable.” “You’re a Mean One, Mr. Grinch” was the original diss track; “Hit Em Up” has nothing on that fire.

6. “All I Want for Christmas Is You” by Mariah Carey Far and away the most recent addition to the catalog of holiday mainstays, “All I Want for Christmas  Is You” was an instant classic and has provided the soundtrack to every drunken ugly sweater party ever since.

5. “Have Yourself a Merry Little Christmas” by Frank Sinatra– Like watching “Miracle on 34th Street” or hearing the phrase, “Every time a bell rings, an angel gets his wings,” this song captures the holiday zeitgeist of the mid-20th century, the golden age of Christmas in pop culture. It’s funny, ’cause there’s a 90 percent chance that Sinatra was doing blow off a cocktail waitress’s tits while recording this song.

4. “Little Drummer Boy” by Bing Crosby and David Bowie– This song and video are amazing and if you disagree I hope your house burns down on Christmas Eve.

3. Baby, It’s Cold Outside” by Margaret Whiting and Johnny Mercer– The chemistry throughout the duet is so pitch-perfect that it completely overshadows the fact that this is a song about a man’s relentless attempt to date rape court a partner.

2. Christmas Eve in Sarajevo” by Trans-Siberian Orchestra– This list could have easily been comprised of nothing but Trans-Siberian Orchestra songs. Their hits, especially “C.E.i.S.” sound as if John Williams, Axl Rose and Dracula were locked in a recording studio together with an oil drum full of Four Loko and a told to compose the perfect Christmas song. There’s few places I’d rather been on Christmas Eve less than Sarajevo, so I don’t understand the title for this song, but I can only imagine this is the kind of music the Bosnians blast as they prepare for civil war, so really this song should be called “Every Day in Sarajevo.”

1. It’s the Most Wonderful Time of the Year” by Andy Williams– No Christmas song encapsulates the joy and enthusiasm of the holiday season like Williams’ version of “It’s the Most Wonderful Time of the Year.” Andy Williams sounds likes the lounge singer at the world’s happiest casino. If Santa has an iPod, which is probable seeing as he has a sweatshop full of elf slaves and apparently limitless resources, this is the only thing on it. Well, that and the video Slutty Claus made for him.

Honorable Mention: “Little Saint Nick” by the Beach Boys, “Santa Baby” by Eartha Kitt, “Christmas Wrapping” by The Waitresses and “Simply Having A Wonderful Christmas Time” by Paul McCartney.

Merry Christmas everyone.

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