The Observer Picks All-Time Best Music for Holiday Season
Monday, December 13, 2021 at 3:13PM
Editor

Greg Wilson/Anderson Observer 

Growing up, nothing said Christmas is coming like the annual release of holiday albums at Firestone and Goodyear. 

Goodyear’s “Great Songs of Christmas” and Firestone’s “Your Favorite Christmas Music” shared a lot of the same artists and songs, and aimed to get dad to the tire store to look at tires while the family purchased the discounted album. 

Those records stacked to autoplay on the turntable of the massive, cherry wood, console in our den filled our house with Christmas music throughout my childhood. The sound of the stylus touching down on a record is something not easy to forget. 

Each album features a collection of holiday songs featuring such artists as the New York Philharmonic, Nelson Eddy, Julie Andrews, Andre Previn, Mitch Miller, Mahalia Jackson, Dinah Shore, Doris Day, Tony Bennett and too many more to name here. 

My family drove to town the first Saturday those records were released each year, but those records were somehow lost in moves and Spring cleanings over the decades. They are collector’s items now, although some of the collections are available on what look to be questionable CD collections. 

Many of these can be found streaming at various sites online.

In the decades since, my collection of Christmas music is almost exclusively digital now, with more than 6,000 holiday songs and more than 3,000 complete albums.

My tastes in holiday music is fairly comprehensive, but many of my favorite cuts were recorded before 1960.  

The only category I generally ignore is novelty Christmas songs from any generation, none of which hold up very well (if they every did), including the abominable “Little Drummer Boy.”

The majority of today’s modern covers of classic holiday music (there are exceptions) pale in comparison to the rich arrangements and musicians whom they seek imitate. Copying vocal licks or trying to make the sound “more modern” rarely works. 

Sadly, it is these songs that start in October on the radio and leave many begging for and early Spring.  

For those who have almost given up on finding the good stuff, here’s a list of holiday albums for almost every mood that will melt the heart of almost any Christmas music Scrooge.

I have divided these records into categories that make sense to me, and hopefully will to you. There is obviously some great music not included here, and I am certain I am missing some jewels. I am also working under the assumption that most folks are streaming at least a large portion of their music now, so I extend mild apologies to audiophile fundamentalists.

But let’s start with the timeless holiday music, listed alphabetically, not ranked in any order. Too many to list top cuts, but all worth a listen. 

Vintage (this list excludes many other excellent Bing Crosby or Frank Sinatra collections, all of which are worth owning) 

“Ella & Louis Christmas” Louis Armstrong and Ella Fitzgerald

Every single duet they recorded works, and they are flawless on this collection. Ella’s “Sleigh Ride” and Louis’ “Cool Yule” as good as things get. Also check out Ella’s “Ella Wishes You a Swingin’ Christmas.” 

“Snowfall” - Tony Bennett

A good holiday showcase for Tony to help you deck the halls. 

“Christmas with Johnny Cash” - Johnny Cash

Compilation of his holiday songs from 1962-1980, these are straight ahead versions of traditional Christmas songs. I wish Cash had done an “American Recordings” holiday album, but he did not, so we get this one and it’s not bad.

“Bells of Dublin” - The Chieftains 

This classic Celtic holiday album, with cuts unfamiliar to many Americans, is a shining star of holiday magic. 

“White Christmas” - Bing Crosby

No surprise here. If you can find the one with the “Jingle Bell outtake/Christmas Wishes to folks back East at Decca Records,” it’s the best. Nothing sings in the holidays like this album. 

“Merry Christmas” - Bing Crosby

Bing, who taught the world how to properly use a microphone, is at his best in the collection of traditional Christmas favorites. 

“Ultimate Christmas,” “A Jolly Christmas from Frank Sinatra” - Frank Sinatra

Both collections of familiar tunes with Sinatra backed by some of the best musicians on earth at the time, all recorded before Old Blue Eyes was in his prime.

Newer

“Christmas” - Bruce Cockburn

One of the finest holiday albums of any era. Cockburn, a stellar guitar player and songwriter, hits so many Christmas joyful notes with both traditional and original material, it never gets old. His “It Came Upon a Midnight Clear” is an epiphany.

“Christmas in the Heart” - Bob Dylan

This record was the but of many jokes when it was released in 2009, and at first listen it is easy to dismiss or even, for some, ridicule. But upon multiple listens, this is a sweet, wonderful Christmas gift from our greatest living songwriter. His voice has the wear of age, and it works here. Those who have little or no appreciation for Dylan are allowed to skip this one, but you are missing a little gem. 

“Cee Lo’s Magic Moment” - Ce Lo Green

An odd, interesting album I expected to hate, but grew more fond of with every cut. Something different, but festive in its own way. 

“Light of the Stable” - Emmylou Harris

Add Neil Young, Dolly Parton and Linda Ronstadt to the best Nashville musicians of the day and you have a sweet, mellow Christmas record fro the ages. 

“Christmas” - Low

I first heard Low’s cover of “Surfer Girl” and have been a fan ever since. Their harmony is a perfect holiday tonic, slow and quiet.

“The McGarrigle Christmas Hour” - Kate & Anna McGarrigle

Recorded in 2005, this record with family and friends - including Emmylou Harris, Rufus Wainwright, Martha Wainwright and Beth Orton - was the last recording before Kate’s death. It is a wonderful and unusual collections of songs for the holidays, featuring not only a couple of traditional carols, but original songs and even Jackson Browne’s “Rebel Jesus.” 

The Mills Brothers Christmas” - The Mills Brothers

Family harmony has never been better, and their take on holiday music is fine indeed.  

“Snow Angels” - Over the Rhine

A bit melancholy, but some wonderful original songs of really blue Christmas emotions and Winter darkness. Excellent.  

“A She and Him Christmas” -She & Him

Zooey Deschanel and M. Ward bring a relaxing record, with excellent, gentle arrangements. The Deluxe 10th Anniversary includes “It’s Beginning to Look at Lot Like Christmas.” 

“Christmas ’64 (rereleased as Christmas Cookin’)” - Jimmy Smith

This one is from 1964, and is full of interesting arrangements with hot Hammond organ solos.

“Songs for Christmas” - Sufjan Stevens

From 2006, this has been on many “best Christmas records” lists ever since and with good reason. Stevens covers so much territory in a joyous holiday journey it’s hard not to smile and sing along. 

Instrumental

“Silent Nights” - Chet Baker

Another compilation of one of our finest trumpet players holiday music. Surprised it is not more widely heard. 

“A Dave Brubeck Christmas” - Dave Brubeck

Piano music to make the holidays merry, bright and chill. A good collection. 

“The Charlie Byrd Christmas Album” - Charlie Byrd

Byrd was not a flashy guitar player, and this understated holiday record shows why he never needed to show off.

“A Charlie Brown Christmas” - Vince Guarraldi Trio

This San Francisco jaaa group hit pay dirt with this record and deserve every penny and every award it earned. It is seamless and is a part of almost everyone’s holiday experience for the past almost 60 years. 

“Six String Santa” - Joe Pass

Joe Pass, maybe the best guitar player of my generation, could not be better in his cover of these Christmas tunes.

“An Oscar Peterson Christmas” - Oscar Peterson 

Cool Jazz from 1955. This guy is one of the kings of the jazz piano and takes a lighter touch here with his six-piece troupe. Fine work. 

“The Ventures Christmas album” - The Ventures

Recorded in the 1964, a surf music spin on the holidays. It grows a bit tiring with each cut, but is something different and fun. 

“The Sound of Christmas,” - The Three Suns

This hard to find record is just plain fun all the way through. 

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