Christmas and Holiday songs: A massive tourney of Yuletide favorites

 

It's the most of wonderful time of the year. And by that, it's time for another tourney of favorites, this time involving some of the best holiday songs of all-time.

There's a strong possibility that every single musician, band and so many more have had their attempt at a Christmas or holiday album. 

Imagine narrowing the many songs produced down, to fit in a tidy little tournament.

It's nearly impossible to do, but it's not impossible to try. And so I did, landing on a supersized bracket to determine which is the favorite out of 128 Christmas and holiday songs. 

In setting out to create a tournament similar to the "Favorite Christmas Film" tournament from a few years back, I arrived at the conclusion that 64 songs was just not going to cut it. At one point, I even toyed with the idea of expanding it all the way to 256 songs but deemed that an undertaking that not even I had the free time for.

The number 128 seemed perfect until I started really digging in.

It might have been easier to simply create a tournament with only the songs and carry no regard for musician or band. Except we end up with a top song that leads into an argument of "yeah, but which artist or which version?"

In the end, a variety of resources (see bottom of this post to see a few) were used in determining which songs to use for this tournament. and roughly where they'd be seeded. Many favorites will likely have been left off and I didn't use anything released in 2020 (sorry Leslie Odom Jr. I do enjoy your Christmas album, though). I did my best to not use too many versions of certain songs and in most cases, artists, but with over 100 years of song versions to sort through, sometimes it's simply unavoidable.

So, without further adieu, the first-round matchups:

Santa Claus region

In the Santa Claus region, we have versions of songs dedicated to the jolly old elf himself, plus songs related to his cohorts and the North Pole. Mixed in are songs about sleigh rides, Frosty, and a couple of wildcards. The top-seed belongs to Gene Autry singing a little ditty about our favorite red-nosed reindeer.

The bracket:

  • 1) Rudolph the Red-Nosed Reindeer - Gene Autry
  • 32) Santa Baby - Macy Gray
  • 16) Jingle Bells - Frank Sinatra
  • 17) Santa Tell Me - Ariana Grande
  • 8) Sleigh Ride - Leroy Anderson
  • 25) Ain't no Chimneys in the Projects - Sharon Jones & the Dap-Kings
  • 9) Little Saint Nick - The Beach Boys
  • 24) Santa Baby - Ariana Grande
  • 4) Santa Claus is Coming to Town - The Jackson 5
  • 29) Jingle Bells - Barking Dogs
  • 13) Santa Claus is Coming to Town - Lou Rawls
  • 20) Frosty the Snowman - The Ronettes
  • 5) Santa Baby - Eartha Kitt
  • 28) Sleigh Ride - Sufjan Stevens
  • 12) Jingle Bell Rock - Bobby Helms
  • 21) Santa Claus is Coming to Town - Michael Bublé
  • 3) Run Rudolph Run - Chuck Berry
  • 30) Santa Claus is Coming to Town - The Four Seasons
  • 14) Frosty the Snowman - Gene Autry
  • 19) Holly Jolly Christmas - Burl Ives
  • 6) Jingle Bell Rock - Brenda Lee
  • 27) Rudolph the Red-Nosed Reindeer - Ella Fitzgerald
  • 11) Rudolph the Red-Nosed Reindeer - The Temptations
  • 22) I Saw Mommy Kissing Santa Claus - The Jackson 5
  • 7) Sleigh Ride - The Ronettes
  • 26) Santa Claus is Back in Town - Elvis Presley
  • 10) Father Christmas - The Kinks
  • 23) Up on the House Top - Alvin and the Chipmunks
  • 15) Little Saint Nick - She & Him
  • 18) Up on the House Top - Gene Autry
  • 2) Santa Claus is Comin' to Town - Bruce Springsteen
  • 31) Santa's Beard - The Beach Boys

White Christmas region

The majority of these songs in this region have – you guessed it – the word ‘Christmas’ in the title. Songs sung by Bing Crosby, John Legend, Judy Garland, and NSYNC are but a few of the musicians and singers you'll find in this region.

The bracket: 

  • 1) White Christmas - Bing Crosby
  • 32) I'll Be Home for Christmas - Joy Williams
  • 16) 12 Days of Christmas - Straight No Chaser
  • 17) We Need a Little Christmas - Johnny Mathis
  • 8) Happy Xmas (War is Over) - John Lennon
  • 25) Let it Snow - Dean Martin
  • 9) White Christmas - The Drifters
  • 24) Christmas Time is Here - Ingrid Michaelson
  • 4) Have Yourself a Merry Little Christmas - Rosemary Clooney
  • 29) I'll Be Home for Christmas - Kacey Musgraves
  • 13) Merry Christmas Baby - Chuck Berry
  • 20) It's Beginning to Look a Lot Like Christmas - Bing Crosby
  • 5) The Christmas Song - Nat King Cole
  • 28) Christmas Mem'ries - Rosemary Clooney
  • 12) White Christmas - Otis Redding
  • 21) It's Beginning to Look a Lot Like Christmas - Michael Bublé
  • 3) Have Yourself a Merry Little Christmas - Judy Garland
  • 30) Silver Bells - Bing Crosby
  • 14) Christmas Eve/Sarajevo 12/24 - Trans-Siberian Orchestra
  • 19) Have Yourself a Merry Little Christmas - The Carpenters
  • 6) The Chipmunk Song (Christmas Don't be Late) - Alvin & the Chipmunks
  • 27) Let it Snow - Boyz II Men/Brian McKnight
  • 11) Ill Be Home for Christmas - Bing Crosby
  • 22) Have Yourself a Merry Little Christmas - John Legend
  • 7) Wonderful Christmastime - Paul McCartney and Wings
  • 26) Merry Christmas, Happy Holidays - NSYNC
  • 10) Christmas (Baby Please Come Home) - Darlene Love
  • 23) I'll Be Home for Christmas - Frank Sinatra
  • 15) Winter Wonderland - Leona Lewis
  • 18) Christmastime is Here - Vince Guaraldi
  • 2) Blue Christmas - Elvis Presley
  • 31) Snow in Sun - Tracey Thorn

Silent Night region

Did Bing Crosby just grab another number one seed? You bet he did. It was actually tough to not include his entire catalog of holiday songs in this tournament, though he sure does show up a lot. He'll have plenty of "Silent Nights" to contend with in this region, however.

The bracket: 

  • 1) Silent Night - Bing Crosby
  • 32) First Noel - John Fahey 
  • 16) First Noel - Vienna Boys Choir
  • 17) Adeste, Fideles - Enya
  • 8) O Little Town of Bethlehem - Jim Reeves
  • 25) Hark! The Herald Angels Sing - Frank Sinatra
  • 9) Silent Night - John Denver and The Muppets
  • 24) First Noel - Andy Williams
  • 4) Do They Know It's Christmas - Band Aid
  • 29) What Child is This? - Burl Ives
  • 13) O Come All Ye Faithful - Nat King Cole
  • 20) Here We Come A-Caroling - Perry Como
  • 5) Peace on Earth/Little Drummer Boy - Bing Crosby & David Bowie
  • 28) What God Wants for Christmas - Darius Rucker
  • 12) Christmas Canon - Trans-Siberian Orchestra
  • 21) Go Tell it on the Mountain - Mahalia Jackson
  • 3) O Holy Night - Christina Aguilera
  • 30) Angels We Have Heard on High - David Archuleta
  • 14) I Have a Little Dreidel - Barenaked Ladies
  • 19) Silent Night - Sarah McLachlan
  • 6) O Holy Night - Neil Diamond
  • 27) Let There Be Peace - Carrie Underwood
  • 11) Believe - Josh Groban
  • 22) Dreidel, Dreidel, Dreidel - South Park
  • 7) O Tannenbaum - Vince Guaraldi Trio
  • 26) O Little Town of Bethlehem - BeBe Winans
  • 10) Mary Did You Know - Pentatonix
  • 23) Little Drummer Boy - Anne Murray
  • 15) Silent Night - Taylor Swift
  • 18) Little Drummer Boy - Perry Como
  • 2) Silent Night - Frank Sinatra
  • 31) Good King Wenceslas - Mel Torme

Candy Cane region

This region is really a hodgepodge of songs, many that could have fit within any of the three other brackets and some with no discernible theme at all, outside of being about Christmas or the holidays.

And this region is represented by Mariah Carey and the top-overall seed.

The bracket:

  • 1) All I Want For Christmas Is You - Mariah Carey
  • 32) Dominick the Donkey - Lou Monte
  • 16) Grandma Got Run Over by a Reindeer - Elmo & Patsy
  • 17) I Want a Hippopotamus for Christmas - Gayla Peevey
  • 8) It's the Most Wonderful Time of the Year - Andy Williams
  • 25) Underneath the Tree - Kelly Clarkson
  • 9) Rockin' Around the Christmas Tree - Brenda Lee
  • 24) A Marshmallow World - Dean Martin
  • 4) Feliz Navidad - José Feliciano
  • 29) Same Old Lange Syne - Dan Fogelberg
  • 13) Please Come Home for Christmas - The Eagles
  • 20) Hard Candy Christmas - Dolly Parton
  • 5) Christmas in Hollis - Run DMC
  • 28) Happy, Happy Christmas - Ingrid Michaelson
  • 12) Chanukah Song - Adam Sandler
  • 21) Mele Kalikimaka - Bing Crosby/The Andrews Sisters
  • 3) Mistletoe - Justin Bieber
  • 30) Lonesome Christmas - B.B. King
  • 14) Christmas Wrapping - The Waitresses
  • 19) Wintersong - Sarah McLachlan
  • 6) Last Christmas - Wham!
  • 27) Baby It's Cold Outside - Louie Armstrong and Velma Middleton
  • 11) What Christmas Means to Me - Stevie Wonder
  • 22) Please Come Home for Christmas - Bon Jovi
  • 7) Where Are You Christmas? - Faith Hill
  • 26) Deck the Halls - Mannheim Steamroller
  • 10) Fairytale of New York - the pogues
  • 23) Grown up Christmas List - Amy Grant
  • 15) Somewhere in My Memory - John Williams
  • 18) Snoopy's Christmas - The Royal Guardsmen
  • 2) You're a Mean One, Mr. Grinch - Thurl Ravenscroft
  • 31) All I Want for Christmas (is My Two Front Teeth) - Spike Jones & His City Slickers
Voting will begin on Twitter (@jasonrh_78) December 1 and continue throughout the month until there is only one song remaining. Check back here for more posts as the tournament continues.

Feel free to comment with some of your favorite versions that did not make this list. Perhaps a second batch will need to be voted on in 2021.

picture credit: Commons.wikimedia

The following were used in helping decide rankings and used for reference:











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