The Greatest Holiday Song of All Time: A Tournament of Music (Preview)

November 18, 2016

This holiday season, many of you will go home and encounter family and friends who, in this recent election, voted…differently from you. For some of you, your minds will be actively scanning for moments of awkward and how to avoid them. Others will be looking to pick a fight.


Here’s my suggested alternative: An innocuous (but lively!) conversation about a subject that people have strong feelings for but, you know, doesn’t really matter at all in the grand scheme of things. Let’s talk about holiday music.

And before you say “Already?? We haven’t even had Thanksgiving yet!”, well, chill out. You should be thankful that we still live in a country that allows holiday music.


So far.




Last year (remember how rad 2015 was?!?), I spent the entire holiday season listening to and analyzing the best of holiday music. I started on the day after Thanksgiving and listened to nothing else until December 26th when I abruptly stopped (because listening to Christmas music the day after Christmas feels like waking up disoriented on Nov. 1st still wearing your “Sexy Bernie Sanders” costume).


And because the season leaves us so quickly, snatching away its merriness, I encourage all of you to start listening now. AND because there is a bottomless catalogue of music from which you can pull (even I am guilty of having added to it at one point), I’ve narrowed it down to the best of the best. But which one actually is the best?


For the next few weeks, I’ll be pitting my favorite songs o’ the season against one another in a knock-down, drag-out brawl of melodic cheer to determine which song is the greatest holiday song of all time. Tournament Style. That means brackets, baby!


And now comes the part where you really freak out: My initial ranking of the Top 64 Songs. This will be the only time I hear any suggestions, acknowledge any omissions or consider any declarations of love for the schmaltz you adore. I’ll formally address all questions and explain the methods behind my Merry Madness of song selection next week. In the meantime, I’m open to your thoughts. So spit ‘em out. The Tournament starts next week…the day after Thanksgiving. On November 25th, Festive Friday, I will release the final bracket.


And now, here we go:


1. The Christmas Song — Nat King Cole (last year’s champ and early frontrunner)

2. White Christmas — Bing Crosby (looking to reclaim the title)

3. All I Want For Christmas Is You — Mariah Carey (strong vertical game)

4. Jingle Bell Rock — Bobby Helms (gritty, perennial favorite)

5. A Holly Jolly Christmas — Burl Ives (oft overlooked despite the high ranking)

6. Have Yourself A Merry Little Christmas — Judy Garland (if this song stays healthy, it can run the table)

7. Santa Baby — Eartha Kitt (a sexy pick with little substance, but anything goes in the top 10)

8. The First Noel — Josh Groban (might get subbed out with the Crash Test Dummies version— not sure yet)

9. Baby It’s Cold Outside — Ella Fitzgerald & Louis Jordan (yes, this version)

10. Silent Night — Susan Boyle (sure, why not)

11. Silver Bells — Bing Crosby (two Bing squads in the top 12 — four in the top 25. That’s a dynasty)

12. Jingle Bells — Frank Sinatra (those J-I-N-G-L-E Bells are actually a distraction — and this unit’s biggest weakness)

13. It’s The Most Wonderful Time Of The Year — Andy Williams (hell yeah it is)

14. The 12 Days of Christmas — The Muppets (the only tolerable version of this song — and even then…)

15. Carol Of The Bells — Pentatonix (these heart attack kids just keep coming back)

16. Joy To The World — Mannheim Steamroller (not pretty, but it wins games)

17. Someday At Christmas — Stevie Wonder (has a legit outside shot at the Final Four)

18. Little Drummer Boy — David Bowie and Bing Crosby (damn, writing this list last December was a happier time)

19. Santa Claus is Coming to Town — Bruce Springsteen (yes, this and not the Jackson 5 version — get over it)

20. Rockin’ Around The Christmas Tree — Brenda Lee (played well all year at Home…Alone)

21. Let It Snow, Let It Snow, Let It Snow — Dean Martin (not intimidated by anything)

23. I’ll Be Home For Christmas — Bing Crosby (you see how this will be a tough fight, right? This is 23?)

24. We Wish You a Merry Christmas — Kenny G (what this team lacks in diversity, it makes up for in stamina)

25. Oh Tannenbaum — Tony Bennett (with Tony, all things are possible)

26. What Child Is This? — Johnny Mathis (Johnny Cash is a close second, but let’s face it — this song wouldn’t stand a chance if Beyonce sang it)

27. I Saw Mommy Kissing Santa Claus — The Ronettes (from possibly the best Christmas album of all time — strong league)

28. Where Are You Christmas? — Faith Hill (this scrappy underdog has its fans. Fans I will never know.)

29. Grandma Got Run Over by a Reindeer — Elmo and Patsy (dark horse, but look out!)

30. There’s No Place Like Home for the Holidays — Perry Como (traffic, Pennsylvania, Pumpkin pie — for some, the nightmare is real)

31. It’s Beginning to Look a Lot Like Christmas — Johnny Mathis (always comes out strong, but can it last well into the postseason?)

32. Happy Xmas (War Is Over) — John Lennon & Yoko Ono (might lack the killer instinct to survive the Christmas carnage we’re about to witness)

33. Here Comes Santa Claus — Elvis (some teams will find it hard to keep up with this uptempo outfit)

34. Christmas (Baby Please Come Home) — Darlene Love (unstoppable from 20 feet out — see if she can penetrate the paint though)

35. Come All Ye Faithful — Bing Crosby (I know! He’s like SEC Football)

36. Oh, Little Town of Bethlehem — Sarah MacLachlan (a pet favorite)

37. Wonderful Christmastime — Paul McCartney (another B squad long shot that echoes previous victors)

38. Up On The Housetop — Jimmy Buffett (relaxed, super high upside)

39. Mary, Did You Know? — Jordan Smith (the newest entry to the field — no one knows what to expect)

40. Away In A Manger — Reba McEntire (I must have been feeling generous on this one)

41. Merry Christmas, Baby — Otis Redding (sitting in prime position for a first round upset)

42. It Came Upon A Midnight Clear — Anne Murray (as her fans like to say, “don’t f*** with Anne Murray, eh”)

43. I’ve Got My Love To Keep Me Warm — Ella Fitzgerald (classic throwback to an era long gone)

44. Sleigh Ride — The Ronettes (I don’t even know who they’d be facing in the first round and I’m already calling an upset. Lock it in!)

45. Happy Holiday — Andy Williams or Brenda Lee (These two artists will have to play in to see who makes the bracket)

46. Winter Wonderland — Eurythmics (sweet 16 dreams are made of this)

47. I Want A Hippopotamus For Christmas — Gayla Peevey (watch out for the lurking mid-majors)

48. All I Want For Christmas is my Two Front Teeth — Spike Jones (see 47)

49. Hark! The Herald Angels Sing — Amy Grant (these fans travel, so every game feels like home)

50. God Rest Ye Merry Gentlemen — Perry Como (when he says it, you believe it)

51. Little Saint Nick — The Beach Boys (I can’t wait to see what happens here)

52. Rudolph The Red-Nosed Reindeer — Gene Autry (was almost disqualified for rhyming “Santa” with “panty” in “Here Comes Santa Claus”)

53. Feliz Navidad — Jose Feliciano (Una historia de Cinderella)

54. Merry Xmas Everybody — Slade (a glam dunk) (you’re welcome)

55. Do You Hear What I Hear? — Carrie Underwood (oh, the boo birds?)

56. Christmas Time Is Here — Vince Guaraldi Trio (we’ll see if this sleepy unit can keep up)

57. Holy Night — Celine Dion (has a tendency to blow opponents out in the first quarter — we’ll see if they can hold on)

58. Deck The Halls — Mannheim Steamroller or Trans-Siberian Orchestra (either way it stinks)

59. Frosty The Snowman — Jackson 5 (there, you happy?)

60. Please Come Home for Christmas — The Eagles (they may not escape the first round, but they’ll definitely cover the spread)

61. Last Christmas — Wham! (this might have to move up to a higher ranking)

62. We Need a Little Christmas — Mitzi Gaynor or Angela Lansbury (Oh I love them both so much, this will be a tough play-in)

63. Blue Christmas — Elvis (the people’s favorite long shot)

64. Christmas Wrapping — The Waitresses (my favorite long shot)

Bubble Songs

65. Mele Kalikimaka — Bing Crosby (listen, the whole division can’t make it into the tournament!)

66. Zat You, Santa Claus? — Louis Armstrong (Zat iz not a word)

67. Run Run Rudolph — Chuck Berry (I know, right? Better luck next year)

68. The Chipmunk Song (Christmas Don’t Be Late) — Dave and The Chipmunks (I just can’t. I put it here so you’d know I was aware of it)

69. I Believe in Father Christmas — Greg Lake (a long fall from whatever glory it once enjoyed)

70. We Three Kings — (Who even sings this crap?)

71. Believe — Groban (no, man)

72. Do They Know It’s Christmas Time — Band Aid (the worst Christmas song of all time. THE ABSOLUTE WORST)


All right, there it is! I look forward to your amazing comments and seeing if any of them sway me. Check back next week for the start of the show!


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