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12 Vintage Christmas Songs That Stand the Test of Time

The holiday season is upon us, and there's nothing quite like the magic of Christmas. From the twinkling lights and delicious cookies to the cherished moments with loved ones, it's a time of warmth and joy. And what better way to enhance the experience than with the perfect Christmas playlist? Just like baking treats for Santa, selecting the best holiday tunes is a special tradition that brings us together.

But with so many songs to choose from, how do you know which ones will truly capture the essence of the season? Look no further than these delightful vintage Christmas classics. They've stood the test of time, evoking memories of holidays past and inspiring new ones for generations to come. Let these heartwarming melodies fill your home and hearts with Christmas cheer.

Related: The Secret Chord That All Good Xmas Songs Use

1. “Hail! Hail! Day of Days” by the Edison Mixed Quartet (1913)

Columbia Records initially rejected this song, deeming it too different from Bessie Smith's usual style. However, it proved to be a Christmas classic. For music enthusiasts familiar with the blues legend Smith, this holiday tune might still be an undiscovered gem, blending Smith's powerful vocals with the enchanting interplay of jazzy horns and piano.

2. “Santa Claus, That’s Me” by Vernon Dalhart (1928)

This is a classic blues Christmas song written and performed by Leroy Carr. The song was released in 1929 and is known for its cheerful and funny take on the holiday season, providing a unique touch to the conventional Christmas song repertoire.

Leroy Carr was a talented blues pianist and singer who gained prominence in the 1920s and 1930s. Carr's collaboration with guitarist Scrapper Blackwell led to many notable albums, and his silky vocal delivery and refined keyboard approach distinguished him in the blues genre.

3. "Winter Wonderland" by Guy Lombardo and His Royal Canadians (1934)

Originally composed by Felix Bernard and Richard B. Smith, Winter Wonderland  has been performed by many artists, but the version by Guy Lombardo and His Royal Canadians in 1934 became a perennial favorite. The magical images of a snowy landscape and the joy of sleigh rides are brought to life by Lombardo's orchestra, which makes it a beloved song that conveys the joyous atmosphere of the holiday season. 

4. “The Fairy on the Christmas Tree” by Three Sisters (1936)

This Christmas tune from 1936 paints a charming picture, transporting listeners to an enchanting ambiance reminiscent of a vintage cartoon film. This song illustrates the stories of little girls who dream of becoming the fairy atop the Christmas tree, adding a nostalgic touch to the festive season. The song evokes childhood fantasies amid crackling fireplaces and twinkling lights, offering an insight into the enduring charm of a holiday season.

5. “The Only Thing I Want for Christmas” by Eddie Cantor (1939)

Eddie Cantor was a popular American comedian, singer, and actor who worked in vaudeville, radio, and early television. The song embodies the spirit of the season and provides a simple and emotional sentiment about the actual meaning of Christmas. Cantor muses on the material goods that many people crave over the holiday season in this song but emphasizes that the only thing he genuinely wants is to be surrounded by loved ones.

Related: This Beautiful Story Unites All Generations at Christmas

6. "White Christmas" by Bing Crosby (1942)

Bing Crosby's White Christmas has become synonymous with holiday cheer and is without a doubt one of the most memorable Christmas songs of all time. Written by Irving Berlin, Crosby's velvety voice croons about dreaming of a snowy Christmas, which evokes an image of a lovely winter paradise. Listeners have long been captivated by this song's ability to transport them to a magical, snow-covered landscape, making it a perennial favorite.

7. "Jingle, Jangle, Jingle" by Kay Kyser and His Orchestra (1942)

Jingle, Jangle, Jingle by Kay Kyser and His Orchestra is a lively and swingin' melody that brings a toe-tapping energy to the holiday festivities. This 1942 release embodies the upbeat spirit of the time and provides the perfect soundtrack for dancing the night away at a vintage Christmas celebration. Its catchy lyrics and infectious rhythm make it a must-have for those looking for a throwback twist on their holiday soundtrack.

8. "Have Yourself a Merry Little Christmas" by Judy Garland (1944)

Featured in the classic film Meet Me in St. Louis, Judy Garland's rendition of Have Yourself a Merry Little Christmas carries a poignant and heartfelt message. Hugh Martin and Ralph Blane's lyrics express the bittersweet emotions that typically accompany the holiday season. Despite its melancholy undertones, the song radiates warmth and reassures us that there is always a place for hope and joy.

9. "Christmas Island" by The Andrews Sisters (1946)

The Andrews Sisters were known for their lively performances and close harmonies, and they really outdid themselves with Christmas Island. A timeless hidden gem, this song gives the holiday season a tropical flair by transporting listeners to a sunny island paradise where the holiday season is celebrated in a whimsical and carefree manner. The catchy melody and playful lyrics are sure to bring a smile to your face and get your toes tapping. 

10. "Let It Snow! Let It Snow! Let It Snow!" by Dean Martin (1945)

Dean Martin's jazzy and joyful rendition of Let It Snow! Let It Snow! Let It Snow! has become a Christmas playlist staple over the decades. The song, written by Sammy Cahn and Jule Styne, is a great celebration of the holiday season, with Martin's smooth vocals inviting listeners to experience a cozy indoor holiday. Its catchy melody and joyful lyrics make it a timeless addition to any Christmas celebration.

11. "Carol Of The Drum" by The Trapp Family Singers (1951)

Carol Of The Drum (aka Little Drummer Boy), from the 1951 CD Christmas with the Trapp Family Singers, is a classic gem that tells the simple story of a young kid bringing his musical gift to baby Jesus. The Trapp Family Singers, famous for their inspiration behind The Sound of Music, deliver a poignant and harmonious rendition that captures the simplicity and spirituality of the season.

Related: The Most Underrated Christmas Movies You Never Saw

12. "Rockin' Around the Christmas Tree" by Brenda Lee (1958)

Brenda Lee's energetic and spirited song injects some rock and roll into the holiday season. Originally written by Johnny Marks, the song exudes a sense of joy and celebration, urging everyone to gather around the Christmas tree and celebrate with one another. Lee's energetic and young performance ensures that the song remains a bright and necessary addition to Christmas playlists.

Thumbnail image source: YouTube/Vevo

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