Vintage Playlist: 20 Tunes for Celebrating the Holidays

by Nicole in Comment — Updated October 28, 2022

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I’m one of a small group people who doesn’t get tired of holiday music! I love the tradition of playing the classics– the greatest names in music history with their voices so rich and reminiscent of the times when folks had those charming transatlantic or deeply southern accents. I get it, holiday music can sometimes seem generic and inescapable, but I invite you to surrender to holiday cheer with this awesome vintage playlist featuring artists whose music is so good we find ourselves saying, “They don’t make music like that anymore…”

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20. What Are You Doing New Year’s Eve – Ella Fitzgerald, 1960

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“When the bells all ring and the horns all blow, and the couples we know are fondly kissing….” Got someone special in mind you’d like to spend New Year’s Eve? Don’t let the chance to ask slip away! If romance is alive and well in your heart, Ella’s flawless version of the song will inspire you to act on your feelings…after it melts you, of course. Its bluesy feel ????

19. Unforgettable – Nat King Cole, 1951

Nat’s version remains the most popular recording of “Unforgettable,” and it’s been over 50 years since it was recorded. Give this a listen with someone you love to love. Slow dance to it in your pajamas in candlelight. Treasure the moment like you’ll never have it again.

18. Baby, I Don’t Cry Over You – Billie Holiday, 1946

The New Year is on the way and if you are ringing it in solo due to a breakup, put this song on blast and sing your heart out! It’ll empower you to find the strength to learn from the past, move forward and acknowledge that you deserve more than you allow yourself to receive in partnerships. And remember: “No man’s man enough to break mah heart…” yea, listen to Billie. She sings the truth, my friend.

17. Auld Lang Syne – Bing Crosby, 1948

Winter and the New Year are symbolic of letting go of the old to make room for the new. The time has come to forget old troubles, old lovers and old habits that are not serving you. Easier said than done, but when you feel to seek freedom from the non-existent past, turn to this timeless melody.

16. Baby, It’s Cold Outside – Margaret Whiting and Johnny Mercer, 1949

This one always makes me laugh…and cringe. It captures the confusing, manipulative dynamic between women and men and gives a fairly accurate impression of the pressure women often feel to say “yes,” when it comes to being pursued, and doing so even though our gut might actually be suggesting we tear ourselves away from the situation before it gets out of control. Really listen to the lyrics and reflect on how you’ve given your power away over the year (not just in dating and relationships) acquiescing to requests you really weren’t sure you wanted to get yourself into. If you’re looking for a resolution, make a commitment to be true to your instincts, intuition and intellect in 2019.

15. Cheek to Cheek – Louis Armstrong and Ella Fitzgerald, 1956

Tis the season to be close, dancing cheek to cheek, in fact. Humans need love to feel a deep sense of connection and well-being. Sign up for classic ballroom dancing lessons and enjoy an evening of meeting new people who share a passion for dance and togetherness.

14. Shout – Temptations, 1963

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I love Motown’s Temptations and I could watch the Christmas/ New Year’s scene from their biographical film all day. I’m not kidding. They’re having so much fun on the stage and I feel it every time.

13. Whilst Shepherds Watched Their Flocks by Night – Trinity Quartet, Early 1900s

I must admit, I am a sucker for chorale music. The writing of this one dates back to 1692! Written by Nahum Tate from Ireland, this carol commemorates shepherds and sings of Christmas traditions.

12. The Fairy on the Christmas Tree – Gracie Fields, 1945

Gracie Fields’ voice is enchanting as she tells a story that everyone can relate to. She certainly made me remember how I felt as a 5 year old, a whimsical dreamer wanting to be “the fairy on the Christmas tree.” Gosh, I’m 27, and I’d still love to be that fairy.

11. White Christmas – The Drifters, 1956

This rendition is in both Home Alone and The Santa Claus! It always gives me that old-time feeling of Christmas and I love the creative liberties the group took to make this classic into a pop blues fusion.

10. You’re a Mean One Mr. Grinch – Thurl Ravenscroft, 1966

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One cannot help but have a soft spot for the stinky, sinister Mr. Grinch. I’ve never heard a more eloquently insulting song. It evokes a shred of pity, and a belly-ache from laughing yourself to tears.

9. Sleigh Ride – Leroy Anderson, 1948

Wordlessly, the instrumental embodies adventure and will transport you to the magical, wintery North Pole where perfectly carved snowflakes are monstrous in size, but soft as clouds. And milk with freshly-baked cookies are gifted to you by Mrs. Claus herself. ::Sigh:: If only…

8. Bring It on Home to Me – Otis Redding and Carla Thomas, 1967

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Originally, Sam Cooke performs this. Both versions are excellent! Either way, everybody could do to have a little R&B Soul around the holidays! I love this one on The Long Kiss Goodnight with the bitterly cold wintry setting and the bad-assery that is Gina Davis.

7. The Christmas Song – Nat King Cole, 1945

The quintessence of the holidays. Right here. Its jazzy, romantic and so familiar it fills me with warmth and makes any situation just that much cozier, whether it be sitting in traffic or standing in long lines waiting for hot cocoa. If chestnuts are roasting on an open fire near me, I’m in a good mood.

6. Silent Night – Paul Whiteman & Orchestra, 1928

It’s sometimes difficult to get through the holidays because it’s so darn cold and because there might be perceived expectations about gift-giving, both of which can be quite stressful. I credit songs like Silent Night for their ability to bring us peace and remind us of the inherent beauty of the season.

5. It’s the Most Wonderful Time of the Year – Andy Williams, 1963

I always forget how heart-warming the holiday season is until Andy Williams sings about it over the radio. When you’re in a “Bah Humbug” kind of mood, cheer up with this jingle-jangle of a tune! You’ll enjoy yourself a lot more this winter if you embrace what it is.

4. Carol of the Bells – Mykola Leotovych, 1919

This Ukranian folk song is originally titled “Shchedryk,” meaning “bountiful,” and was meant to be a well-wishing song. The harmonies in a minor key and those descending scales always give me goosebumps. It’s haunting in its own beautiful dark way.

3. There’s No Place Like Home for the Holidays – Perry Como, 1954

Like home, this version has so much character and captures the spirit of being where you grew up and where your loved ones are. Peace and chaos, easy-going and stressful- Perry Como’s version is expressive and evokes nostalgia.

2. Have Yourself a Merry Little Christmas – Judy Garland, 1944

If you haven’t seen “Meet Me in St. Louis,” please give this classic some time. Nothing helps you through the holidays like films from days of old– perfect in their black and white frame, speaking to the heart of simpler times.

1. Santa Baby – Eartha Kitt, 1953

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This is undeniably my favorite Christmas melody. I’m not a much of a material girl, but I’m amused by the expensive taste and sense of entitlement in the lyrics. Eartha Kitt’s sweet silky voice softens the weight her exorbitant demands, and she sings the lyrics with such flirtation and simplicity. No lie, I put this one on repeat and sing it to Santa in my best “good girl” voice.

Happy Holidays everyone! May this playlist fill you with a comfort and soulfulness that brightens your days and brings warmth to your smile!

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