Ray Charles — Rudolph the Red Nosed Reindeer
Dean Martin's version is also good ("Rudy the red-beaked reindeer"), but nothing can beat Ray Charles's delivery. His entire Christmas album is great, including a version of Baby, It's Cold Outside with Betty Carter.
The Pogues and Kirsty MacColl — Fairytale of New York
An amazing song from an amazing band.
"Happy Christmas your arse, I pray God it's our last."
Judy Garland — Have Yourself a Merry Little Christmas
The very best rendition of this song, from a great movie that is sentimental in the best way. A classic.
Thurl Ravenscroft — You're a Mean One Mr. Grinch
Ravenscroft had such a wonderful voice and his delivery of Dr. Seuss's lyrics have let people indulge in their inner Grinch for decades.
The three words that best describe you,
Are as follows, and I quote,
"Stink! Stank! Stunk!"
Bruce Springsteen — Santa Claus Is Comin' to Town
You can't beat Bruce for pure exuberance, and his version of this "kiddie" song manages to rock out, be fun, and let people know why he and the E Street Band have been such a hot ticket all these years.
Barenaked Ladies (with Sarah McLachlan) — God Rest Ye Merry Gentlemen / We Three Kings
This version is not afraid to play with a more traditional Christmas carol. Its casual vibe captures the mood of caroling and eggnog and Christmas cheer.
John Denver and the Muppets — We Wish You A Merry Christmas
This is just too much fun, from a television special Kermit and the gang did with John Denver in 1979.
There is a ton of holiday music out there. Some other favorites include:
Feliz Navidad — Jose Feliciano
Little Drummer Boy — Bing Crosby and David Bowie
Holiday Christmas: War is Over — John Lennon
The Christmas Song — Nat King Cole
I'll be Home for Christmas — the Carpenters
Santa Baby — Eartha Kitt
The Most Wonderful Time of the Year — Johnny Mathis
And of course,
White Christmas — Bing Crosby
But I'm not done. I'll soon be compiling my list of some of the worst holiday songs ever made ...