A List of Holiday Music that Still Brings Joy to the World

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. 

Each of those albums 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. 

Those records stacked to play until the last record dropped 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 and hearing the holidays beckon is something not easy to forget. 

There are more than 50 selections, annd many 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 6,400 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 ever did), including the abominable “Little Drummer Boy.”

The majority of today’s modern covers of classic holiday music (there are rare 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. Plus, the production lacks the live musician feel of the earlier records when multi-track recording was non-existent. 

Sadly, it is these modern songs that start in October on the radio and leave many begging for the holidays to be over and for an 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.

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, for hard copies of some of these choices are difficult to find.

Here are my picks for timeless holiday music: 

“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. 

“Ella Fitzgerald’s Christmas” – Ella Fitzgerald

Easily the most straight-ahead Christian holiday record on this list, with Ella working her magic on 11 songs of the season of Advent.

“Ella Wishes You a Swinging Christmas” – Ella Fitzgerald

From 1960, Ella lights up the holidays with 18 tracks guaranteed to make spirits bright. “Sleigh Ride” is subdued but a fine cover, while “Let It Snow! Let It Snow! Let It Snow!” will make you wish it were Christmastime in another era.

“Christmas Songs by Sinatra” – Frank Sinatra

A throwback to the 1940s (recorded in 1948), with a mixture of sacred and secular Christmas music, “Christmas Dreaming” is as good as it gets. The “Christmas Carol Medley,” a cut from the “The Guest Star” radio series, always brings big smiles at my house.

“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.

“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 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. 

“Lumières d'hiver” – Emilie-Claire Barlow

Wonderful arrangements of less recorded holiday songs. Barlow’s voice is perfect for these songs, and her “Christmas Waltz” is light the warm lights of the Christmas tree. Most of these songs are in French, but that won’t dampen your enjoyment of this record.

“The Pianoman at Christmas” – Jamie Cullen

A bit over-the-top at times, but still a fun sleigh ride of traditional tunes.

“The Classic Big Band Christmas Album” – Compilation

Some seriously good holiday songs, many of which are not often found elsewhere. Many of these are from 78rpm recordings including Charlie Spivak’s “A Winter Wonderland” and the excellent arrangement of “Snowfall” by Claude Thornhill and his Orchestra.

“Jingle Bell Swing” – Various Artists

This one includes cuts by Duke Ellington, Miles Davis, Louis Prima, Carmen McRae and the very odd Art Carney rap holiday song from 1954. Some solid music on this one.

“Christmas Songs” – Diana Krall

Still carrying the torch for the old sound, Krall swings her way through a dozen holiday favorites. The final cut, “Count Your Blessings Instead of Sheep” is second only to Bing’s version.

“Santa’s Funk & Soul Christmas Party, Vol. 2” -Various Artists

This one is worth a listen if only for Pearl Bailey’s “Jingle Bell Cha Cha,” which rings with the underrated singer’s vibe. The very weird “Satna Fly,” featuring Martin Mull and the Sondra Gaskin Glee Club, is as funky as the holiday gets.

“A Very Swingin’ Basie Christmas” - The Count Basie Orchestra

Swell record to put on while decorating the tree or wrapping holiday gifts. 

“The New Possibility: John Fahey’s Guitar Soli Christmas Album/Christmas with John Fahey” – John Fahey

John Fahey has made a habit of recording a new album of Christmas music every five or six years, but The New Possibility, which was originally released in 1968, is still his best. On it, Fahey has pulled off the near miraculous feat of taking old holiday chestnuts like "Joy to the World" and "It Came upon a Midnight Clear" and making them sound fresh. When he plays a Travis-picking version of "O Come All Ye Faithful" or he recasts "Silent Night, Holy Night" as bottleneck blues, you get the feeling Fahey is treating the music with respect rather then piety. Also included in this reissue are six tracks from his 1975 release Christmas with John Fahey, Vol. II. 

“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 Guaraldi 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. 

“Christmas Album” – Herb Albert and the Tajuana Brass

A mellow album for Albert, but the songs are well chosen and the arrangements just right.

“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. 

“Sounds of Christmas” – Ramsey Louis Trio

From 1961, one of the best Christmas jazz alubms, with some of my favorite arrangements of holiday music. A lot of sonic variety.

“The Sound of Christmas,” - The Three Suns

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

“God Rest Ye Merry Jazzmen” – Various Artists

Also hard to find, this fine record includes  Dexter Gordon Quartet, McCoy Tyner, The Arthur Blythe Quartet, The Heath Brothers, Paquito D’Rivera, and The Wynton Marsalis Quintet.

“A Mellow Jazz Christmas” – Various Artists

Stanley Clarke, David Benoit, Phil Woods, ‘nuff said. This brings a smooth but cool vibe to the holiday.

“A Merry Christmas” – Stan Kenton

Ambitious arrangements, big brass and orchestral percussion make this one special.

“Yuletide Swing” – Oliver Jones

New one for me this year. Tasteful and chill arrangements without getting syrupy. Nothing spectacular, but you might have this one playing at holiday gatherings for a while.

“Merry Ole Soul” – Duke Pearson

Soulful piano decks the halls of this album with nine cuts of gospel/blues infused holiday joy, including a surprisingly lively, yet traditional, “Silent Night.”

“7 Shades of Snow” – June Bisantz

This EP has echoes of June Christy’s early 1960s stuff (even a cover of “The Merriest”), with strong musicians and a gentle vibe.

“Christmas” – The Singers Unlimited/Leader: Gene Puerung

Maybe the best caroling album of holiday favorites. Recorded in 1971, all A Capella groups need to listen to these folks to see how to do it right. Really warm and relaxing holiday music. 

“Christmas Vibes” – Warren Wolf

Channeling Lionel Hampton, Wolf holiday vibes his way through a fairly standard list of classics. Along the way, he finds a sweet spot in such cuts as “Christmastime is Here.”

“Jingle Bell Jazz” - Various Artists

Scat singing, Herbie Hancock and a Dixieland “Frosty the Snowman” make this worth a listen. 

“Crescent City Christmas Card” – Wynton Marsalis

Swinging sleigh rides through some of the standard canon, with Marsalis’ arrangements and solos taking center stage. If you are tired of holiday music, tune in her.

“Christmas Tree-O” 

Fun and clever covers of holiday favorites make this one a lot of fun.

“Matt Wilson’s Christmas Tree-O” – Matt Wilson

Not to be confused with the other tree-o, Wilson’s is unlike any other Christmas album you’ve heard befor, with crazy and fun spins on these songs to make a record special. Jeff Lederer on Sax, Paul Sikivie on Bass, and Matt Wilson on Drums.

“Merry Magic” – Eric Reed

Jazz piano great Reed is in fine form in this mostly instrumental holiday album.  A shining organ take on “Oh Come, All Ye Faithful” and the keyboard work in “Angels in the Snow” are the most memorable cuts.

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