Music · Nostalgia

12 Nostalgic Days of Christmas: 7 Underrated Classic Christmas Songs You Will Love {Seventh Day}

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Last Monday we featured 11 modern Christmas songs destined to become classics. For those of us who grew up listening to “classic” Christmas songs from the likes of Bing Crosby and Frank Sinatra, it’s sometimes challenging to listen to modern Christmas recordings and have the same feeling we get when songs like White Christmas or Sleigh Ride come on the radio. 

And that’s even true for contemporary remakes of those old classic standards. For me, it seems like only when the modern versions sound like the classic versions (a la Michael Bublé on, well, pretty much every song he sings) or when a new recording harkens back to a classic style (a la Brett Eldredge on Glow) do I feel that similar sense of nostalgia I have when Nat King Cole sings the Christmas Song. Now I’ve never had roasted chestnuts on an open fire, but when the guitar and strings and piano start playing the first few bars and Nat starts in with his gentle, pitch-perfect voice on his definitive 1961 recording, it takes me back. So many classic songs do that, and this time of year the local radio plays a fair amount of them, interspersed among the more recent holiday efforts by Carrie Underwood, Trans Siberian Orchestra and Justin Bieber.

But what about some of those classic recordings that never get radio play? The ones nobody really talks about, but which deserve a place among the great traditional Christmas songs? Obviously personal taste comes into play for any list like this. But for my money, these 7 songs are simply among the best. They, like so many other holiday classics, fill my heart with the Christmas spirit and remind me of the days of my youth, filled with family and friends and lightness and simplicity and hope and happiness—all things I want to have my own daughter experience today and remember in the future.

As you know through reading this blog, nostalgia can be powerful stuff, and it’s my goal to embrace all the positive benefits of nostalgia whenever and wherever I can. Listening to classic Christmas songs like these are part of my daily journey to use the past to create better days today, for me and my daughter.

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So I hope you enjoy these highly underrated classic Christmas recordings. Some, like Robert Goulet’s version of Have Yourself A Merry Little Christmas, are outstanding versions of well-known songs, and some, like Christmas Toast by Bing Crosby, are not well known, but hit all the right notes to make you . . . feel.

And isn’t that what music is supposed to do?


1) Have Yourself A Merry Little Christmas – Robert Goulet

Robert Goulet’s voice has a big and bold nostalgic quality, and this classic version of this classic song makes me want to have a merry little Christmas every. single. day. (And you all know he sang You’ve Got  A Friend In Me at the End of Toy Story 2 right?)


2) Christmas Toast – Bing Crosby

This song is a perfect vehicle for Bing’s smooth, soothing voice. Why it isn’t as big as White Christmas, I’ll never understand.


3) I’ll Be Home For Christmas – The Osmonds

I love the harmonies of those Osmond brothers–and Marie. This song starts the double album “Osmond Family Christmas,” and this song just feels like Christmas and snow and home.


4) Santa Claus Is Coming to Town – The Carpenters

Karen Carpenter’s angelic voice in a sultry version of a song about Santa Claus? Brilliant. Just brilliant. This is the original version before they messed with that middle horn section.


5) Whatever Happened to Christmas – Frank Sinatra

Okay, I understand that this is a song of lost love and is a bit sad. But I feel that you can listen to this song and use the emotion that it stirs within not to lament the loss of the past, but to remember and embrace the wonderful things that Christmas can be today and in the future, and use that to make today happy, warm, and fulfilling.  


6) That Spirit of Christmas – Ray Charles

A song featured in Chevy Chase’s movie, Christmas Vacation, when he is stuck up in the attic watching home movies. As a song written in the 80’s, it’s not quite as “classic” as some of the others, but because it has that lovely vintage Christmas sound and feeling, the addition of it to this list is easy.  And because, well, Ray Charles.


7) That Holiday Feeling – Steve Lawrence & Eydie Gorme

When Eydie sings “You think you’re such a smarty” and Steve sings “C’mon let’s have a party,” I dare you to not fall in love with this song.  This song makes me happy. This song should make everyone happy. Listening to it will definitely give you That Holiday Feeling.  And isn’t that what we want this time of year?


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Just joining us for this series? The links below can help you catch up:

12 Nostalgic Days of Christmas: 1 Christmas Infographic {First Day}
12 Nostalgic Days of Christmas: 2 Holiday Gift Guides {Second Day}
12 Nostalgic Days of Christmas: 3 Nostalgic Traditions {Third Day}
12 Nostalgic Days of Christmas: 4 Nostalgic Crafts to Create with Your Kids This Christmas {Fourth Day}
12 Nostalgic Days of Christmas: 5 Classic Christmas Cookies {Fifth Day}
12 Nostalgic Days of Christmas: 6 Ugly Christmas Sweaters {Sixth Day}

Tomorrow’s Eighth Day of Christmas is .gif wrapped just for you!

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