Celebrating the holidays with vintage Christmas songs

Few things get me excited about the magic of the holiday season like Christmas songs. Before I’ve even blown out the candles in my jack-o-lanterns, I’m usually humming a few bars from Frosty, Rudolph or Silver Bells. There’s something thrilling wonderful about having songs that we (by and large) only get to hear and sing for a few short weeks a year.

When I was growing up my parents were very keen on Christmas tunes, playing a menagerie of festive records, tapes, and later CDs, each a smidge different from its music shelf neighbours. Many were rich in old school tunes, others were very of the moment, some fell in between and others were a delightful jumble of songs from many eras and crooners.

As such my taste in Christmas music is rather diverse, yet the warmest spot in my holiday tune loving heart is reserved (naturally) for vintage Christmas songs, those beautiful classics that were performed by some of the best artists of the 1930s, 40s, and 50s. These are the songs that have become soundtracks for the world’s holiday season, played as often in Hollywood movies as in shopping malls, at gala parties and as the background music at countless holiday dinners.

They’re the songs that I associate with the gripping chill of frosty nights, the taste of piping hot apple cider, the unmistakable rustle of wrapping paper being portioned off the roll, and the simply joy of a multi-coloured string of twinkling lights strung around a freshly chopped fir tree. These are traditional tunes that I poured over the lyrics of in our family’s well-thumbed copy of the Reader’s Digest Merry Christmas Songbook, never tiring of imagining that I was an old fashioned caroller.

Reflecting fondly on those sweet, joyful memories of youth and celebrating the bounty of holiday favourites that I cherish in my heart today, I thought it would be delightfully fun – and festive! – to gather up twenty beautiful Christmas songs sung (or preformed) by artists and groups from our beloved mid-twentieth century era.

Below you’ll find YouTube videos of some of the best holiday songs of all-time. These are some of the tunes that radiate an endless sense of Christmas cheer, of festive goodwill, and the happiest of tidings. Given the unpredictable nature of how long music videos stick around on YouTube sometimes, I can’t guarantee that all of these videos will still be up until December 25th, but most of them should be, and moreover the selection itself is a great starting point for your Christmas playlist.

So don your coziest red vintage sweat, gather in the light of a glowing fireplace, and join me in listening to the following selection of timelessly fantastic vintage holiday songs.






~ The Christmas Song ~


{Also known as “Chestnuts roasting on an open fire”; a 1944 jewel of a song written by Mel Tormé and Bob Wells, preformed by the endlessly wonderful Nat King Cole.}



~ I’ll Be Home for Christmas ~


{Scores of crooners from Perry Como to Dolly Parton have covered this 1943 holiday classic, though few could do it as soulfully as Elvis, whose version appears here.}




~ Santa Claus is Coming to Town ~


{You can hear history itself reverberating in the notes of this song – which was first joined the holiday music ranks in 1934 – as Tommy Dorsey and his orchestra play a richly melodic version of it here (tell me you don’t just love the recording crackling in the background?).}



~ Baby, it’s cold outside ~


{The perfect holiday tune for romantics, this delightfully fun duet from 1944 is a favourite of both my mother and I, who agree that few versions can compare with the recording above from ’49 by Dinah Shore and Buddy Clark.}



~ Have Yourself a Merry Little Christmas ~


{Exquisitely sung by the silken voiced songstress Ella Fitzgerald, I find this upbeat version of a mid-40s to be a great tune for lively holiday cocktail parties classic (side note: this song first appeared in the 1944 film Meet me in St. Louis with Judy Garland).}



~ I’ve Got My Love to Keep Me Warm ~


{A lively holiday song that was penned by Irving Berlin in 1937, this delightful tune is perfect for the whole winter, especially when sung by a charming voice like that of 1950s darling Kay Starr.}



~ Marshmallow World ~


{A delightfully fun holiday tune that always put a smile on my face (and makes me crave marshmallows! :D), this playful song was written in ’49, and preformed here (in the 60s) by the endlessly wonderful duo that was Frank Sinatra and Dean Martin.}



~ Jingle Bells ~


{There are few more iconic Christmas songs in the world than this timeless number. First published in 1857, the version here is a purely instrumental big band version by Benny Goodman and his orchestra.}



~ The Night Before Christmas ~


{Admittedly, this a spoken poem/story, but this version by Louis Armstrong is so immensely lovely that listening to it is something that I always try to in my holiday festivities. If you have any children in your life, gather them ‘round and share in the reading Dickens’ traditional tale together, it’s too fantastic not to listen to as a family.}



~ The Little Drummer Boy ~


{This serene song (which was originally called “Carol of the Drum”) was written in 1941 by Katherine K. Davis, though it is the iconic version above that was recorded nearly two decades later by Harry Simeone that many of us most associate with this deeply touching Christmas song.}



~ Frosty the Snowman ~


{A favourite of children (and the young at heart) since its 1950 debut, this darling song about a snowman that magically comes to life, is extra delightful when enjoyed by the first group to record it: Gene Autry and the Cass County Boys.}



~ Silver Bells ~


{If the holiday season had but one song to launch it on its merry way each year, this would unequivocally be it for me. Though many think of the lovely version by Bing Crosby and Carol Richards when calling this tune to mind, I have a soft spot for the original 1950 recording by Bob Hope and Marilyn Maxwell.}



~ Here Comes Santa Claus ~


{A Christmas Eve anthem for little girls and boys for generations now, this charming song first appeared in 1947 and was quickly covered by numerous artists in the following year – including a sweet gal named Doris Day in 1949, whose version is included here.}




~ Winter Wonderland ~


{Upbeat and flat-out fantastic (if you ask me), this song is one of those dear tunes that instantly sets the holiday mood for me – especially if it’s the chipper version by those swing era enchantresses, the Andrews Sisters.}


~ Mistletoe and Holly ~


{This late 1950s Christmas song is one that I think deserves to get more play. It’s a light-hearted, wholesome tune with a simple message of holiday cheer that really sparkles when sung, as it is here, by Ol’ Blue Eyes himself.}




~ Away in a Manger ~


{Harkening back to the 19th century, this serene song has a lullaby-like quality (particularily when sung by Nat King Cole, as it in this version) that I can’t help but associate with being sleepy as a child, my belly full of eggnog and shortbread cookies, on Christmas Eve night as I hung up my stocking, feeling as though an eternity would pass before I’d be able to take it down and retrieve my gifts from its fuzzy interior.}



~ Let It Snow ~

{When the first tissue thin flakes began to fall here last week, this was the song that I ran to play. Beautifully sung by Rosemary Clooney, this vintage version is sure to warm you up with happiness on even on the chilliest of snowy days.}



~ Sleigh Ride ~


{This fantastically lovely instrumental burst onto the Christmas song scene in 1949, and to this day no one can top the classic Boston Pops version above that has helped make this tune a holiday mainstay for over six decades now.}



~ White Christmas ~


{No roundup of vintage Christmas songs would be complete for me without the endlessly beautiful version of White Christmas that Bing Crosby sang in the tune’s namesake movie. To me this song is the embodiment of everything that is right, ageless, and amazing about vintage Christmas music.}


~ What Are You Doing New Year’s Eve? ~


{This elegant, romantic holiday song is the perfect number to play during the span of festive days between Christmas and New Year’s, especially if it’s the stellar version by none other than the beautiful Lena Horne.}




The selection of marvellous holiday songs above is but the tip of the festive tune iceberg. Thanks to the fact that many Christmas carols and songs are decades (and in some cases, centuries) old, a great deal of them have been recorded by a vast array of artists over the years. Many singers that tie in with our beloved vintage era – such as Frank Sinatra and Bing Crosby – even recorded whole Christmas albums over their own over the years, meaning that there’s a decent chance that you can find many more of your holiday favourites by fantastic yesteryear music stars.

I hope that you enjoyed this festive playlist, it is chalked full of some of my favourite holiday classics (it was tricky to limit this list to just twenty, as I could have easily kept going to fifty or more!). I would love to hear about your most beloved Christmas songs – be they vintage or modern renditions – as I’m always looking to expand my repertoire of holiday tunes.