Playwright and composer – creator of the musical Group

The 50 Greatest Christmas Songs

This list contains no synths, drum machines or auto-tuned vocals (my apologies to Taylor Swift and Justin Bieber). These are my favorite versions of the best 50 Christmas songs. Feel free to comment below regarding the songs I egregiously missed, as I’m sure there are many.

If you want to listen to the first 30 songs of this playlist, here they are on Spotify:

  1. The Christmas Song – Nat King Cole: If God doesn’t sound like Nat, I’m going to be sorely disappointed. His buttery, soulful voice rests gently on a bed of strings and jazz guitar. It’s perfection. (Alternative version: Mel Torme wrote this classic and his live version on the Traditional Christmas Classics album is a tour de force of loveliness)
  2. White Christmas – Bing Crosby: I prefer the slightly less racist version from the White Christmas movie than the one from Holiday Inn. The strings and choir take turns backing up Bing’s deep, deep, deep tone. Besides, there is a brief whistle solo. How great is that?
  3. Merry Christmas Darling – Carpenters: This song has AMAZING harmonies, a gorgeous performance by Karen and the word Christmasing used as a verb. Sidebar: Every time I hear this song while in Los Angeles it makes me wish I was with my family in Michigan. Sidebar2: It has an 11 second saxophone solo. Any longer and it would be that song with a lame saxophone solo.
  4. This Christmas – Donny Hathaway: Donny co-wrote this classic. Do not accept alternative versions. Chris Brown’s version is the version that pops up first when you search for this song. Fix this, America.
  5. Skating – Vince Guaraldi Trio: No one made jazz music as accessible as Vince. The change that happens in this song at the one minute mark is extraordinary. How can you hear this and NOT think of skating?
  6. Let It Snow, Let It Snow, Let It Snow – Frank Sinatra: 1:38, Frank says, “but that fire is mmmmmmmmm delightful.” (Alternative version: If it wasn’t for the “mmmmmmm delightful,” I was going to choose Harry Connick Jr’s version)
  7. Baby It’s Cold Outside – Johnny Mercer, Margaret Whiting: It’s difficult to get the right chemistry for this song. It has to be sexy, but subtle. James Taylor is too sweet and Dean Martin is trying too hard to liquor her up. This classic version is tonally perfect.
  8. Sugar Rum Cherry (Dance of the Sugar Plum Fairy) – Duke Ellington: If you saw the Nutcracker a million times but haven’t heard Duke Ellington’s versions, do yourself a favor and do it, like now. You will instantly feel cooler. They are all great.
  9. Christmas Scat – Muppet Christmas Carol: It’s only 23 seconds long, but it is perfect. Try to picture Robin on Kermit’s shoulder and NOT smile.
  10. Carol of the Bells – George Winston: I LOVE this song and George’s piano version is freakin’ gorgeous. For some reason I imagine myself eating waffles while listening to it. You’ll have to ask my mom why that is. (Alternative versions: Pentatonix has a really cool acapella version and the Piano Guys has a great string version.
  11. Happy Christmas (War Is Over) – John & Yoko: Imagine a world where this song will no longer be relevant. (This would be higher if it weren’t for Yoko’s backup vocals – I don’t think she broke up the Beatles or anything, she just can’t sing)
  12. Dona Nobis Pacem – Richard Stolzman: If you don’t know this GORGEOUS song, check it out. It is beautiful and peaceful and has a 100% chance of calming you down at all times. (The translation means “Give Us Peace”)
  13. (It Must’ve Been Ol’) Santa Claus – Harry Connick Jr: This may be the most fun song on this list. You just want to hang out with this band.
  14. Christmas Time Is Here – Vince Guaraldi Trio: I prefer the instrumental version, but it’s great with vocal too. Vince is simply integral to all of my holidays.
  15. All I Want For Christmas Is You – Mariah Carey: This is probably the best modern Christmas song. This song explodes with energy and Mariah is at her best. (Alternative Version: Michael Buble’ has a nice version, but it doesn’t match Mariah’s energy)
  16. That Was the Worst Christmas Ever! – Sufjan Stevens: This is the only song on the list that I listen to year round. It’s so beautiful and sad.
  17. All That I Want – The Weepies: I lied in #16, I listen to this song year-round too. This is right up my alley.
  18. God Rest Ye Merry Gentlemen / We Three Kings – Barenaked Ladies & Sarah McLachlan: Both of these songs can be slow. Combining them and picking up the tempo was a brilliant choice. This song is fun and the harmonies are kind of brilliant. (Alternative versions: For an instrumental We Three Kings, look upSteven Sharp Nelson. I also recommend Harry Connick Jr’s ragtime version of We Three Kings)
  19.  Sleigh Ride – Ella Fitzgerald: I love the instrumental version of this song (particularly the Boston Pops classic), but if you are looking for vocals, go with Ella. Always. As a rule. (Alternative version: The She & Him version is pretty fun, but it is a little too rockabilly for my taste)
  20. Jingle Bells – Michael Buble’ featuring The Puppini Sisters: He was born in the wrong time period. Such a classic voice. This is an upbeat, big band version that has the Puppini Sisters sounding like they are from a 1920’s radio show. (Alternative version: I really like Barbara Steisand’s double time Jingle Bells too)
  21. Christmas Waltz – Carpenters: Again, Karen Carpenter’s voice is all sorts of Christmas and the arrangement is amazing. Plus, not many songs talk about the meter: “And this song of mine, in ¾ time…” I think I’m going to start all of my songs this way in the future. “Coming to you in 4/4, as I march you out the door.” (Alternative version: Nancy Wilson has a lovely take on it)
  22. It’s Beginning To Look A Lot Like Christmas – Johnny Mathis: This would be higher but I hate his A Marshmallow World so much it taints all of his music for me.
  23. Winter Wonderland – Peggy Lee: This is a great version of the only song I know of that asks you to conspire by the fire.
  24. Twelve Days of Christmas – John Denver w/ the Muppets: This repetitive song is almost unlistenable unless you are singing along, UNLESS you have the Muppets singing it. This version still makes me laugh and I’ve heard it more than you. Trust me.
  25. I Saw Three Ships – Sting: This version is a bit of a song cycle with great percussion and flutes. It sounds nothing like any other Sting songs I can think of. The bass that kicks in at 1:20 is perfection.
  26. Santa Baby – Eartha Kitt: Yes, Madonna does a great job covering this song, but she is just doing an impression of the AMAZING Eartha Kitt.
  27. The Holly and the Ivy – Mannheim Steamroller: I’m hesitant to include work by Steamroller because they often relied on synthesizers that date their music terribly. This, however, is really pretty.
  28. I Pray on Christmas – Harry Connick Jr: Try to not sing along. Just try.
  29. Rudolph the Red Nose Reindeer – Billy May w/ Alvin Stoller: A mambo version of Rudolph with a crazy screaming guy? Yes, please.
  30. Santa Claus Is Comin’ To Town – Bruce Springsteen: This would be pretty rough as a studio track, but LIVE, it truly lives. Hearing the band crack each other up is a real joy. (Alternative version: Jackson 5: because it’s great)
  31. Holly Jolly Christmas – Burl Ives: I really struggled between this classic version and Michael Buble’s updated version. They are both great.
  32. The Christmas Blues – Dean Martin: A lovely melody that fits Martin’s vibrato perfectly. Listen to how he sings “Jan-u-a-ry”
  33. Auld Lang Syne – James Taylor: This is an amazingly beautiful version of this song. The piano and guitar work perfectly together with James, who sounds as brilliant as ever.
  34. It Came Upon A Midnight Clear – Josh Groban: Look, you aren’t going to find a better voice than Josh Groban. His musical choices, however, are often a little too “soft music” station for me. This version, however, is pretty unique. The simple chord changes he has made makes the song feel free.
  35. Christmas Time All Over the World – Sammy Davis Jr: A lovely message that works because of Sammy’s amazing vocals.
  36. I Was Thinking I Could Clean Up For Christmas – Aimee Mann: This isn’t a very traditional Christmas song, but it is a traditional sounding Aimee Mann song, which is all right with me. Sidebar: This song contains the only swear word on this entire list.
  37. Angels We Have Heard On High – Sufjan Stevens: In the hands of most artists, this song is kind of boring. Sufjan’s version is a lovely surprise. (Alternative version: Sixpence None the Richer have a pretty great take on the song as well)
  38. Christmas Is Coming – Vince Guaraldi Trio: Sorry, he had to be on here three times. I love this song. If you don’t clap twice along with the snare rim shot (at 0:47 and :50), you aren’t living.
  39. Joy To The World – Nat King Cole: Tried to find a better version for the sake  of variety. Could not.
  40. Have Yourself a Merry Little Christmas – Mel Torme: It starts with just his voice and then the strings emerge ascending and descending following his lead. It’s stunning. (Alternative version: James Taylor’s is perfect as well)
  41. I’ll Be Home For Christmas – Bing Crosby: Listen to the Spanish guitar gently plucking over the strings. It’s impossible to sing this song without copying Bing’s way of singing “If only in my-Y-y dreams” (Alternative version: Nickel Creek has a truly unique version of it that is great).
  42. Silver Bells – Stevie Wonder: He makes this song kind of cool. He makes everything cooler.
  43. Riu Riu Chiu – The Monkees: It’s kind of wrong to have a Spanish song on this list as sung by The Monkees, but the harmony is really good.
  44. The First Noel – Trans-Siberian Orchestra: I don’t find the electric guitar that the Trans-Siberian Orchestra typically uses as being very timeless. This song, however, is just a perfect acoustic guitar.
  45. Some Children See Him – James Taylor: This rarely covered song is really pretty. I simply love the melody and it fits Taylor’s voice so, so well.
  46. Christmas Lights – Coldplay: This kind of sounds like every Coldplay song, but that’s okay. It’s still good. All their stuff is pretty good. Admit it.
  47. O Holy Night – Pentatonix: This song is pretty but it can be kind of boring. I particularly like the harmonies in this version and I love hearing Kirstie Maldonado take the lead on this one. The four men in the group tend to dominate.
  48. I Saw Mommy Kissing Santa Claus – Jackson 5: He watched long enough to see him go from kissing to tickling? Stop peeping Michael.
  49. Christmas Card From a Hooker in Minneapolis – Tom Waits: I love this song but I only feel comfortable putting it on a Christmas list near the bottom. You know… because Hooker is in the title and it’s not everyone’s cup of tea. (Alternative version: Neko Case does an AWESOME version of this song)
  50. Little Drummer Boy / Peace On Earth – Bing Crosby & David Bowie: I kind of hate Little Drummer Boy, which is why it’s so low on my list, but the Peace On Earth counter part really works for me. Sidebar: if you haven’t seen Will Ferrell and John C. Reilly sing this, click here. (Alternative version: I’m shocked how much I like Josh Groban’s version. He tries something new with it that certainly makes Little Drummer Boy more interesting than it deserves.)

Good Songs Omitted:

Blue Christmas – Elvis: I think his vocals are great, but the repetitive backup vocals just kill me.

Feliz Navidad – Jose Feliciano: I have no excuse for this not being on the list. It’s a classic.

Fairytale of New York (particularly the version by Gianni and Sarah): I couldn’t get over one particular word in the middle.

Frosty the Snowman – Mike Jones: This is a really great piano version. It should have been on here.

The Chipmunk Song – Alvin And The Chipmunks: I actually like this song, but the chipmunk voices make it not quite worthy of the top 50 list.

Terrible Songs Omitted:

Do They Know It’s Christmas – Band Aid:  If this song wasn’t for charity, I would tell you how I really feel about it..

Marshmallow World – Johnny Mathis: This song angers me.

Wonderful Christmastime – Paul McCartney: As catchy as the melody is, those synths are devastating

Mistletoe – Justin Bieber: Has he ever sounded as white as he does in this song?

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