Top 25 Holiday Songs of All Time – Craig’s List

OK, so I know there might be a few songs missing that are considered classics, but these are my favorites:

1. The Christmas Song (Nat King Cole)
Plain & Simple – The Gold Standard of Holiday songs by the Gold Standard of vocalists.
2. White Christmas (Bing Crosby)
Bing’s Merry Christmas album with the Andrews Sisters is the best.
3. Merry Christmas Darling (The Carpenters)
A contemporary standard, of which there are few.
4. Christmastime is Here (Vince Guaraldi)
The music from Charlie Brown’s Christmas is classic and not just for kids. Scores of jazz musicians were influenced by Guaraldi, and this tune captures the mood and spirit perfectly.
5. Do You Hear What I Hear (Whitney Houston)
Despite the turmoil in her personal life, Whitney has perhaps the most incredible pipes of any pop singer of her era. Her version of the Star Spangled Banner at the Super Bowl with the Marine Band backing her brings chills down the spine (and like these other pop start wannabees, she did it live).
6. It’s the Most Wonderful Time of the Year (Andy Williams)
Not a huge fan of Williams in general, but I love his Holiday music. This is the most quintessential of his many Yuletide tunes.
7. You’re a Mean One Mr. Grinch (Thurl Ravenscroft)
I learned something researching this one. I thought it was sung by Boris Karloff who narrated the cartoon. Turns out he was given credit by mistake.
8. Peace on Earth/Little Drummer Boy (Bing Crosby & David Bowie)
I remember watching this live on Bing’s Christmas special back in the 70’s as I recall. Seemed like an odd pairing at the time, but it turned out to be a wonderful collaboration.
9. Silent Night (Barbara Streisand)
Many versions to choose from, but I like this one. Barbara’s A Christmas Album ranks among the best.
10. Let it Snow! Let it Snow! Let it Snow! (Steve Lawrence & Edie Gorme)
OK, so Saturday Night Live and others have taken their shots at Steve & Edie, but I’m telling you this version really swings.
11. O Tannenbaum (Oh Christmas Tree) (Vince Guaraldi)
Charlie Brown part 2.
12. William the Angel (Rob Mathes)
Better known in the music business as a producer and songwriter, Rob Mathes performed this song in his PBS concert Christmas is Coming: Rob Mathes & Friends with Vanessa Williams and Michael McDonald. An instant classic.
13. Some Children See Him (Sixpense None the Richer)
I remembered George Winston’s instrumental version from his December album, but the lyrics are so beautiful and I found this version that’s mostly acoustic guitar and vocals. Singer Leigh Nash has a childlike quality to her voice (You may remember the group’s hit single Kiss Me) that seems appropriate.
14. Winter Wonderland (Dean Martin)
Dean does the fun holiday with that twinkle in his eye and playful vocal quality that we love. There are two arrangements of this one, but there’s one I listened to as a kid that’s really great. Believe it or not, it came from a compilation album that Texaco gas stations used to give away will a fill-up back in the dark ages, as I tell my son.
15. Away in a Manger (Mahalia Jackson)
Really brings you back to the spirit of Christmas.
16. Mele Kelikimaka (Bing Crosby & the Andrews Sisters)
Fun tune and a nice departure from snow and fireplaces.
17. Feliz Navidad (Jose Feliciano)
Adds a nice international flavor to the list. This one also has stood the test of time.
18. Frosty the Snowman (Jimmy Durante)
From the television special – with Durante, like Louis Armstrong, Louis Prima, and Dean Martin, there’s an audible smile in every note he sings.
19. Sleigh Ride (Johnny Mathis)
Again, many versions, but I like the way Mathis interpreted this one.
20. Oh Holy Night (Nat King Cole)
Another one that just sounds better by Nat.
21. Silver Bells (Bing Crosby & Carol Richards)
From the Bing Crosby album previously referenced.
22. I’ve Got My Love to Keep Me Warm (Dean Martin)
Great tune not as widely known or recognized as a holiday tune until Rod Stewart butchered it on his standards album.
23. Baby It’s Cold Outside (Blossom Dearie & Bob Dorough)
This song is a classic that has been recorded by hundreds of artists. This version is somewhat obscure – by two eclectic pianists/songwriters and jazz club performers also known for their work in the Schoolhouse Rock series.
24. The 12 Yats of Christmas (Benny Grunch & the Bunch)
This one is essentially for New Orleanians by the king of colloquial musical references, Benny Grunch.
25. Santa Bring My Baby Back (To Me) (Elvis Presley)
This one rocks and it just makes me chuckle. It almost sounds like someone doing a bad Presley impersonation.