Who Sang It Best? (Holiday Edition)

“Have Yourself a Merry Little Christmas”

  1. Frank Sinatra Have Yourself A Merry Little Christmas * Frank Sinatra * (HD) - YouTube
  2. Kacey Musgraves (from her Xmas special)
  3. Jeremy Messersmith
  4. Pretenders
  5. Jewel (from the Sing-Off soundtrack)
  6. Ella Fitzgerald
  7. Sarah McLachlan
  8. Michael Bublé
  9. She & Him
  10. Francesca Battistelli (Live)
    Honorable mention: Dina Shore
    Steer clear of versions by: Christina Aguilera, Josh Groban, Perry Como, Carpenters
    “The Christmas Song (Chestnuts Roasting on an Open Fire)”
  11. Mel Tormé - YouTube
  12. Natalie Cole
  13. Perry Como
  14. Rhonda Vincent
  15. Carmen McRae
  16. James Taylor
  17. Seth MacFarlane
  18. Catherine Feeny
  19. The Monkees
  20. Aimee Mann
    Honorable mention: Ella Fitzgerald
    Fails: Tony Bennett, She & Him, Sheryl Crow
    I tried doing a ranking for “O Holy Night”, but just could not find anyone who could hold a candle to Mariah Carey’s roof-raising gospel rendition. Bing Crosby’s is fine for what it is, and if you prefer an ethereal, reverent version you could go with Celine Dion’s. But Mariah’s performance is so electric, it has ruined me for all the others. Mariah Carey - O Holy Night (Official HD Video) - YouTube

For “Have Yourself…”, I’m quite partial to this John Denver/Jim Henson rendition.

I know I’m a heretic for this, but Madonna’s version of Santa Baby is far and away the best version.

Ditto U2 and “It’s Christmas (Baby Please Come Home)”

And, to round out my Gen X triumvirate, John Mellencamp owns I Saw Mommy Kissing Santa Claus

Is there a reason why Judy Garland’s original of “Have yourself a merry little Christmas” and Nat King Cole’s iconic version of The Christmas Song (Chestnuts) were not on the list? Because for me, those two versions are the best.

I don’t have time right now to listen to all the listings (it’s always so much easier when a YouTube link is included), and I haven’t heard them all. I’m familiar with Sinatra’s “Have yourself…” and it’s fine, but I really prefer the original, more poignant lyrics that Garland sings instead of “hang a shining star upon the highest bough” (she sings “until then we’ll have to muddle through somehow”).

Hands down the best "Have Yourself … " is David Seville from “Christmas With the Chipmunks volume 2.” Especially in context with the whole album. An island of sincerity in the midst of chaos.

I like those lyrics fine (and BTW, my highly-ranked Jeremy Messersmith version uses them or something pretty close: https://www.youtube.com/watch?v=qf4RJ-Cbr_I), but I don’t like the Judy Garland version because of the tone of her vocals: too “warbly”, you might say.
I hadn’t heard Nat King Cole’s version of “The Christmas Song”, but although I still don’t think it beats Mel Tormé (and I’d call his original the truly iconic one, given that he wrote the song and I’d never even heard of NKC’s version), now that I’ve heard it I’d rank it a solid second, ahead of his daughter Natalie.

I like the Madonna version of “Santa Baby”, but I don’t think it beats Eartha. I don’t know any other version of"It’s Christmas (Baby Please Come Home)" than U2’s, but I do like that song.I can’t go with you on John Mellencamp though. My heretical take on that song is that there’s nothing in the lyrics to indicate an unreliable narrator, so I suspect the songwriter wrote a risque song about adultery with Santa Claus and then retconned a story about it being the kid’s dad to get out of the doghouse with the Catholic archdiocese.

The John Denver part is very nice indeed, but for me the Jim Henson aspect ruins it (it was probably perfectly cromulent on the Muppet TV special). I wish Denver had done it on his own.

I don’t agree that it’s “hands down the best”, but it’s definitely a very good version. I had not heard it, but it would make my top five.