Ranking The 30 Best Christmas Recordings Of The 20th Century

Ready your playlists!

30. The Royal Guardsmen, “Snoopy’s Christmas (Christmas Bells)”

Released: 1967

The Royal Guardsmen co-opt the success of the Peanuts to bring you a story of love and peace when the fabled German aviator The Red Baron and Snoopy participated in a truce for Christmas during World War I. Despite its seemingly preposterous origins, this song has somehow manage to survive the test of time.

29. Elton John, “Step Into Christmas”

Released: 1973

Obviously you need a Christmas song from Elton John, and, instead of another cover of “White Christmas,” Sir Elton brings us “Step Into Christmas,” which is among the most upbeat Christmas songs ever recorded.

28. Alvin and the Chipmunks, “The Christmas Song (Don’t Be Late)”

Released: 1958

The Christmas song that always seems to resurface on your local 24/7 Christmas Music radio station about two weeks into the non-stop Christmas music calendar, Alvin, Simon and Theodore (also known as a sped-up tape) sing to you about the glories of the hula hoop because, well, Chipmunks.

27. José Feliciano, “Feliz Navidad”

Released: 1970

The official Christmas song of suburban schools looking to add some multicultural flair to their Christmas pageants, José Feliciano’s Feliz Navidad could have some of the most repetitive and simple lyrics in the history of music.

26. Carnie and Wendy Wilson, “Hey Santa!”

Released: 1993

One of the great Christmas pop ballads of the 1990s, the Wilson sisters’ “Hey Santa!” is probably more influential than we give it credit for being.

25. Gene Autry, “Rudolph The Red-Nosed Reindeer”

Released: 1949

Rudolph began as a gimmick for a department store, but he has evolved into everyone’s favorite flying magic reindeer thanks to this classic Gene Autry recording. It seems that now no Christmas album is complete without a cover of “Rudolph.”

24. Andy Williams, “The Most Wonderful Time Of The Year”

Released: 1963

When Staples used this song for Back to School season advertisements, it catapulted this crooner classic back into the world’s consciousness. Want to know more about Andy Williams? Ask your grandparents.

23. John Denver and The Muppets, “The Twelve Days of Christmas”

Released: 1979

John Denver and The Muppets teamed up for an album and a television special in 1979 because they were among the biggest things in entertainment that year. I wonder if the puppets were actually present in the recording studio. I hope so.

22. Charles Brown, “Merry Christmas, Baby/Please Come Home For Christmas”

Released: 1960

Leave it to a blues musician to get a hit with a Christmas song. Despite more famous covers from Bon Jovi and The Eagles, the original is the best.

21. Wham!, “Last Christmas”

Released: 1984

Wham!’s “Last Christmas” represented a serious paradigm shift in the world of Christmas music, bringing the sub-genre back into pop relevance.

20. George S. Irving and Dick Shawn, “Snow Miser and Heat Miser”

Released: 1974

You didn’t think we were going to get through this list without at least one Rankin/Bass stop motion song, so here it is from 1974’s The Year Without a Santa Claus. Who do you prefer? Heat Miser? Snow Miser?

19. Perry Como, “(There’s No Place Like) Home For The Holidays”

Released: 1959

Perry Como sings about an idealized version of the holidays that never really existed. Nevertheless, listening to this song makes you want to put on a cardigan.

18. The Beach Boys, “Little Saint Nick”

Released: 1963

“Little Saint Nick” is exactly what you would expect a Beach Boys Christmas single to be, which is probably because it’s practically identical to “Little Deuce Coupe” (released by the band about 5 months earlier).

17. Frank Sinatra, “Jingle Bells”

Released: 1948

Frank Sinatra’s Christmas recordings are a staple of just about every Italian-American home this time of year. He’s one of the most important Christmas musicians of all time and best appreciated on cassette in your elementary school bus’ audio system.

16. ‘N Sync, “Merry Christmas, Happy Holidays”

Released: 1998

The 1990s saw a revival of the pop-Christmas scene. Nearly every major pop act since has produced a Christmas album usually featuring no more than a couple original songs and recordings of more traditional standards. ‘N Sync’s 1998 album, Home For Christmas, was one of the last Christmas albums of the 20th Century. Its single, “Merry Christmas, Happy Holidays,” is a classic of the 1990s Christmas music genre.

15. Harry Belafonte, “Mary’s Boy Child”

Released: 1956

Harry Belafonte is probably the only person that could make a calypso-inspired, overtly religious tune popular for more than half a century.

14. Dean Martin, “Baby, It’s Cold Outside”

Released: 1959

“Baby, It’s Cold Outside” is one of our strangest holiday songs. Its two parts (male and female) are labeled in the score as “Wolf” and “Mouse” respectively, and the song itself is about trying to convince a girl that doesn’t want to stay the night to do just that. It’s basically Robin Thicke’s “Blurred Lines” for a different period of time. Dean Martin has the right balance of swagger and desperation to make the song work without seeming (too) rapey.

13. Thurl Ravenscroft, “You’re A Mean One, Mr. Grinch”

Released: 1966

The often attributed to someone else “You’re A Mean One, Mr. Grinch” is one of those songs that’s so different from the rest of the standard Christmas fare. Also, you know you’ve wondered what a “three-decker sauerkraut and toadstool sandwich with arsenic sauce” might be like.

12. Elvis Presley, “Blue Christmas”

Released: 1957

Elvis had a voice that really lent itself to holiday music, and “Blue Christmas,” which was originally recorded by Doye O’Dell in 1948, is a standard of the country Christmas repertoire. Elvis’ version is the most famous and best version of this slightly more depressing Christmas ballad.

11. Vince Guaraldi Trio, “O Tannenbaum”

Released: 1965

Charlie Brown and the rest of the Peanuts gang are an important Christmas television tradition in many American homes. Vince Guaraldi’s soundtrack to the CBS Christmas special, A Charlie Brown Christmas, is loaded with instrumental jazz versions of many Christmas standards including “O Tannenbaum.”

10. Bobby Helms, “Jingle Bell Rock”

Released: 1957

Bobby Helms’ greatest success in his career was “Jingle Bell Rock.” While the song has been covered by acts ranging from Hall and Oates to Dr. Teeth and the Electric Mayhem (Yes, the Muppet band), the original rockabilly version is still the best.

9. John & Yoko/Plastic Ono Band, “Happy Xmas (War Is Over)”

Released: 1971

John Lennon and Yoko Ono originally intended this song as a protest to the Vietnam War, but, over time, the song has become a popular target for covers and a standard on Christmas radio and at Christmas parties.

8. Stevie Wonder, “Someday At Christmas”

Released: 1967

Probably one of the best all-around Christmas albums is Stevie Wonder’s Someday At Christmas. Its title track is just the kind of sappy Christmas ballad that makes you want to sit inside, drink some cocoa, and watch the snow fall.

7. Jackson 5, “Frosty The Snowman”

Released: 1970

Starting from the first vocal line, Michael Jackson’s high-pitched “Oh, Frosty,” this version of the song about a magical hat that animates a snowman is the best of its many recordings.

6. Bruce Springsteen and the E Street Band, “Santa Claus Is Coming To Town”

Released: 1985

Nobody brings “Santa Claus Is Coming To Town” to life quite like the Boss. Joined by the E Street Band, Springsteen’s version of the song isn’t the only version ever released, but it’s the only one you need to care about.

5. The Drifters, “White Christmas”

Released: 1954

“White Christmas” may be one of the most-recorded Christmas songs of all time. A lesser-known version is this one by The Drifters from 1954. For my money, it’s the best recording of the song (with apologies to Bing Crosby).

4. Brenda Lee, “Rockin’ Around The Christmas Tree”

Released: 1958

Brenda Lee was one of the top-selling artists of the 1950s and 1960s, but her best-known song remains to be 1958’s “Rockin’ Around The Christmas Tree,” which took on a new life after featuring prominently in the 1990 film Home Alone.

3. Bing Crosby & David Bowie, “The Little Drummer Boy / Peace On Earth”

Released: 1977

You cannot make a post about Christmas music without including Bing Crosby, who is a titan of the Christmas genre. Joined here by David Bowie, in one of television’s greatest juxtapositions of personalities, the two sing a duet of “The Little Drummer Boy” mashed up with “Peace On Earth,” a song that was written for the TV special that featured this scene. Crosby died a few weeks after the scene was recorded, but his catalog of Christmas classics lives on.

2. Nat King Cole, “The Christmas Song”

Released: 1946

Nat King Cole is the King of Christmas music, and his recording of “The Christmas Song,” acutely demonstrates his ability to transport you, through music, to a fabled winter village.

1. Mariah Carey, “All I Want For Christmas Is You”

Released: 1994

There is no song more popular on today’s playlists of Christmas music than Mariah Carey’s “All I Want For Christmas Is You.” It is, despite all the formidable competition, the greatest Christmas recording of the 20th Century.

Is your favorite Christmas song not ranked? Add it below!


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