The 25 Best Christmas Oldies That’ll Take You Back

Few things nurture the festive spirit around the holidays like a playlist brimming with Christmas oldies.

From jovial pop-style tunes to ballads sung by some of the world’s most famous crooners, there are tunes to suit virtually every taste.

While countless new Christmas songs are recorded almost every year, festive oldies capture the season’s spirit better than most. There’s a reason why many of the most famous hits from decades past have been recreated by many newer artists.

Whether planning a nostalgic playlist to transport you back to your childhood Christmases or hoping to appeal to all generations at this year’s holiday party, you’re in the right place.

Here are some of the best Christmas Oldies worth listening to this year.

1. “Jingle Bell Rock” – Bobby Helms

First released by Bobby Helms in 1957, “Jingle Bell Rock” is one of the most popular festive tunes ever. It receives frequent airplay on US radio stations around the holidays and inspires a host of cover tributes from other artists.

The song is steeped with elements of rockabilly and country with a catchy set of lyrics you just can’t help but sing along.

2. “Rockin’ Around the Christmas Tree” – Brenda Lee

Written by Johnny Marks and recorded by the incredible Brenda Lee in 1958, “Rockin’ Around the Christmas Tree” is a true festive classic. With plenty of unique sounds delivered by saxophone, piano, and bass players, this song is brimming with life.

Interestingly, Lee recorded this song when she was only 13, though her voice sounds wonderfully mature and rich.

3. “Feliz Navidad” – Jose Feliciano

Though it was initially recorded in 1970, “Feliz Navidad” slowly gained popularity among Christmas music lovers in the years that followed. Well-known singers, including Michael Buble and Garth Brooks, covered the tune. However, we still recommend listening to the original.

The single was recorded when Feliciano was feeling particularly homesick at Christmas, so it’s packed with heartfelt emotion.

4. “Silent Night” – Bing Crosby

Based on the beloved Christmas carol first written in 1818, “Silent Night” by Bing Crosby is a popular tune on the airwaves during the holidays. It’s a relaxing, magical song ideal for soothing the kids on Christmas Eve or just winding down on Christmas night.

The carol was even declared an “intangible cultural heritage” by UNESCO in 2011.

5. “Run Rudolph Run” – Chuck Berry

If you’re looking for classic rock and roll in your Christmas playlist, you can’t go wrong with Chuck Berry. Though Berry recorded this song in 1958, the title is credited to Johnny Marks and M. Brodie due to their ownership of the Rudolph character.

The song is a 12-bar blues tune, musically similar to well-known releases like “Johnny B. Goode.”

6. “Santa Claus is Coming to Town” – Jackson 5

If you want to go back a few years with your Christmas playlist, you can always consider listening to the original version of this song, produced in 1934. However, the Jackson 5 version is a lot more fun.

Created as part of the group’s Christmas album in the 1970s, you just can’t help but sing along to this song. If you want to check out a different artist, more than 200 have recorded this song over the years, so you’ll have plenty of options.

7. “Blue Christmas” – Elvis Presley

Though sadder than some of the tunes on this list, Elvis Presley’s “Blue Christmas” is a tune you can’t miss from a real festive oldies list.

The song was initially written by Billy Hayes and Jay W Johnson, then famously recorded by Elvis in 1957. If you’re feeling a little homesick around the Christmas season, this rhythm and blues song is ideal for you.

8. “It’s the Most Wonderful Time of the Year” – Andy Williams

Though it was originally released in 1963, this song remains extremely popular. It even hit number 21 on the UK Singles chart in 2007 and constantly appeared in the top 10 during the 2000s.

Thanks to its light-hearted, warm, and festive notes, the tune has appeared in countless Christmas advertisements and movies.

9. “Santa Baby” – Eartha Kitt

This sultry Christmas tune by Eartha Kitt was written by Philip Springer and Joan Javits in 1953. This tune is an excellent addition to any playlist, a relatively cheeky track at the time, highlighting the extravagant wish list of many women back in the sixties.

The song has been parodied and referenced in various films and television series over the years.

10. “Let It Snow! Let It Snow! Let It Snow!” – Dean Martin

While Ella Fitzgerald also recorded this song in the early years, Dean Martin primarily popularized it. The song was written by Jule Styne and Sammy Cahn, who penned the lyrics during a heatwave in July, dreaming of a “white Christmas” someday in their future.

Though the song does not refer to Christmas, it’s still a popular festive tune.

11. “Have Yourself a Merry Little Christmas” – Judy Garland

There’s something about this Christmas classic that warms the heart. Produced by Judy Garland in 1944, the tune is one of the most popular Christmas oldies of all time.

In fact, in 2007, ASCAP announced it was the third most performed tune in the previous five years. There’s also a version of this song available from Frank Sinatra, with slightly modified lyrics.

This is the kind of tune that would pair perfectly with an evening watching festive Hallmark movies.

12. “Sleigh Ride” – The Ronettes

Originally composed as an orchestral song by Leroy Anderson in 1948, “Sleigh Ride” exploded in popularity when it was produced again by The Ronettes in 1963.

One of the most played songs on the US airwaves during the Christmas season, this light-hearted and memorable tune will get you in the mood for festive walks and snowy scenery.

13. “The Christmas Song” – Nat King Cole

What would a list of Christmas oldies be without a mention of Nat King Cole? Commonly subtitled “Chestnuts Roasting on an Open Fire,” this classic was released in 1946 as part of Nat King Cole’s fantastic Christmas album.

The original recording was inducted into the Grammy Hall of Fame in 1974, thanks to its impact on festive music.

14. “White Christmas” – Bing Crosby

No matter how you feel about Christmas music, you can’t deny this tune is a classic.

Initially, the song was recorded by Irving Berlin. However, it was made most famous by Bing Crosby, who aired his recording on an NBC show on Christmas Day.

The tune is one of the best-selling singles of all time, and it’s something virtually every family will be able to sing along with.

15. “I Want a Hippopotamus for Christmas” – Gayla Peevey

Not all classic Christmas tunes need to be conventionally traditional. If you want something a little more unique to your playlist, this tune is sure to brighten your day.

Recorded by 10-year-old Gayla Peevey in 1953, the song will surely bring a smile to your face. Plus, it’s a great song for people of all ages, making it ideal for child-friendly holiday parties.

16. “Frosty the Snowman” – Jimmy Durante

Speaking of child-friendly Christmas songs, “Frosty the Snowman” is another must-have you’ll likely be familiar with today.

Although the tune was originally recorded by Gene Autry and the Cass County Boys, most people remember the Jimmy Durante version, also featured in the stop-motion holiday special aired on television sets worldwide.

17. “I’ll Be Home for Christmas” – Frank Sinatra

Recorded by several cover artists over the years, including some alternative rock bands, “I’ll Be Home for Christmas” is a classic tune you won’t forget.

The lyrics remind us the best gift of the holiday season is spending time with your loved ones. Plus, Frank Sinatra’s voice is truly incredible.

18. “Little Saint Nick” – The Beach Boys

Although this song isn’t quite as old as some of the other tunes we’ve covered on this list, it still belongs on any classic Christmas playlist. “Little Saint Nick” is brimming with Beach Boys Charm, fun lyrics, and energetic music you can’t help but sing along to.

The song appeared as the first track on the Beach Boys’ official Christmas album released in 1964.

19. “Please Come Home for Christmas” – Charles Brown

If you’re looking for some blues to go alongside all the green and red of the festive season, this is the song for you. Written and released in 1960, the song is a beautiful crooning ballad, all about missing an estranged love.

It was also re-recorded by Jon Bon Jovi later if you want something with a slightly rockier vibe.

20. “Holly Jolly Christmas” – Burl Ives

Written by Johnny Marks, best known for his other amazing festive songs like “Rockin’ Around the Christmas Tree,” “Holly Jolly Christmas” was released in 1965.

Performed by Burl Ives, the music has become one of the 25 most-performed holiday songs, according to ASCAP. Various well-known modern artists, such as Michael Buble, have also covered the track.

21. “I Saw Mommy Kissing Santa Claus” – Jimmy Boyd

This song is an unforgettable part of Christmas culture, written by Tommie Conner and recorded by American singer Jimmy Boyd in 1952. The tune has been covered by various bands over the years, though the Jackson 5’s 1970s version is probably the most famous.

Interestingly, the song was condemned by the Roman Catholic Church in Boston because of its “adulterous” themes.

22. “Peace on Earth” – Bing Crosby

Another phenomenal Christmas track by Bing Crosby, “Peace on Earth,” or “Little Drummer Boy,” was recorded alongside David Bowie in 1977.

The song was performed on Crosby’s television special in the same year and featured a duet of two different tunes. This song is one of Bing Crosby’s last recordings before his passing.

23. “Happy Xmas (War Is Over)” – John Lennon

Recorded by John Lennon and Yoko Ono in 1971 with the Harlem Community Choir, this phenomenal song was intended to be a protest against the Vietnam War.

The soaring lyrics and wonderful melody will stick with you long after the festive period. With such a solid, emotional message, it’s no wonder this track became a festive hit.

24. “Winter Wonderland” – Dean Martin

Packed with fun and bouncy lyrics, Felix Bernard first wrote and recorded “Winter Wonderland” in 1934 in collaboration with Richard Bernhard Smith.

Though there’s no reference to the holidays in the lyrics, this tune still screams “Christmas classic,” mainly when performed by the excellent Dean Martin. The song was released on his Christmas album in 1966.

25. “Do You Hear What I Hear?” – Whitney Houston

Finally, if you like a classic carol in your Christmas playlist, Whitney Houston’s version of “Do You Hear What I Hear” is a fantastic choice. Produced in 1987, the song benefits from Whitney Houston’s incredible voice and fantastic confidence.

For modern music lovers, there’s a 2019 version remixed by Pentatonix worth checking out too.

The Ultimate List of Christmas Oldies

Hopefully, this list has given you plenty of unique Christmas oldies to add to your playlist this festive season. Remember, you can always shake things up a little bit by combining the past and the present.

Why not match classic Christmas songs with more unusual or modern tracks for a customized festive experience?