Holiday Music that Brings Joy to the World (and Swings)
Greg Wilson/Anderson Observer
This list is revised and updated
It’s way past beginning to look a lot like Christmas, and, like it or not, holiday music is everywhere.
As much as I have always loved the music of the season (my collection of more than 7,500 mostly pre-1960 holiday tunes continues to grow), I understand why so many others do not. Much of what fills the radio and department stores this time of year is painfully bad.
Seemingly every artist feels compelled to recycle pablum arrangements of Christmas music standards, or worse yet, write one of their own. It’s enough to make Santa lock down his best pair of noise-cancelling earmuffs and load up on TUMS.
Like any other genre, most of the pedestrian fair cranked out every year is the audio equivalent of Taco Bell’s endlessly searching for ways to make their menu appear to offer something really new, which it never does.
But there are shining gems buried in the mountain of holiday music. Much of it was recorded more than 60 years ago by artists who are mostly long gone. But many more modern talented jazz and soul musicians have brought new life and new music worthy of decking the halls.
Access to almost all of this music is readily available on streaming platforms. (I have the major ones, and rank them: 1. Spotify, 2. Pandora, 3. YouTube Music 4. Apple (improving), 5. Tidal, 6. Amazon Music)
My tastes in holiday music are fairly comprehensive, with the exception of the novelty Christmas songs, none of which hold up well, including the silly attempt at religious kitsch of the abominable “Little Drummer Boy.”
While majority of today’s modern covers of classic holiday music (there are rare exceptions) cannot compare to the rich arrangements, musicianship and vocals whom they seek imitate, there are exceptions. These are the ones which almost capture the live-musician feel of the earlier records when multi-track recording was non-existent and there was an energy in the recording sessions that can be felt listening to those sessions.
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.
It also works 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. Check out this Spotify playlist for samples of the music below.
Vocalists. Pick any of the big band singers or crooners from the late 1930s-early 1960s and you will find a lot of good stuff. Bing Crosby, Frank Sinatra, Ella Fitzgerald, Dinah Shore. Rosemary Clooney, Dean Martin, etc., and you will find something you like.
“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.
“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.
“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” - 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 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.
“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” – The Singers Unlimited/Leader: Gene Puerung
Maybe the best caroling album of holiday favorites. Recorded in 1971, every a capella group need to listen to these folks to see how to do it right. Really warm and relaxing holiday music.
“Christmas with the Andrews Sisters”
If you have heard these sisters’ tight harmony, you know what to expect. Bing Crosby shows up on three cuts as a bonus. Engaging.
“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.”
“Christmas Secrets” – Enya
The Scottish singer brings her trademark ethereal voice to the season, and with a chill experience. If you haven’t heard 'Oiche Chiuin' (Gaelic version of “Silent Night”), dial this one up.
“Wonderland: Cool December” – Various
Ella Fitzgerald, Billie Holiday, Pearl Bailey, Bing Crosby, Dean Martin, Julie London, Arte Shaw and John Pizzarelii are part of this yuletide collection.
“Jingle Bell Swing” – Various
Another swell compilation with Miles Davis, Louis Prima, Duke Ellington and more swinging on the holly decking the halls.
“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.
“Cold Dark Nights” – Sam Phillips
Her most recent album, featuring a few solid originals, traditional stuff and, of course, Sam’s great voice.
“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.
“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.
“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.
“Christmas Carousel” – Peggy Lee
From 1960, these 12 songs pepper in a few lesser known tunes and Lee’s voice was made for egg nog seaon.
“The Pianoman at Christmas” – Jamie Cullen
A bit over-the-top at times, but still a fun sleigh ride of traditional tunes.
Big Band, Jazz, Swing, Instrumental
“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. This album never gets old.
“Sounds of Christmas” – Ramsey Louis Trio
From 1961, one of the best Christmas jazz albums, with some of my favorite arrangements of holiday music. A lot of sonic variety
“From the Sony Vault: Christmas with the Big Bands” –
Tex Beneke, Frankie Carle, Benny Goodman, Russ Morgan, Arte Shaw, Harry James and other lead some of the hottest musicians in energy filled, fun and warm classics and some that are not classics.
“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.
“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.
“Hymns, Carols and Songs about Snow” – Tuck Andress
A couple of tracks do have vocals by his wife Patty, but this guitar work will brighten any holiday home.
“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.
“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.
“Only Gift” – Andrew Morgan Smith and the Lifetimers
Great percussion adds a fine groove to this one. I dare you not to like “O Swing All Ye Faithful.”
“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.”
“Christmas at My House” – Larry Carlton
Legendary jazz guitarists brings a smooth, but never boring, vibe to seasonal favorites.
“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 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 before, 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.
“A GPR Christmas” – Various (multiple volumes)
Another modern holiday classic, with Tom Scott, David Benoit, Diane Schuur, Lee Ritenour and others.
“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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