Holiday Tunes that Swing and Bring Joy to the World

Greg Wilson/Anderson Observer

It’s Christmas season 2024, and every year some songwriter attempts to write a great new holiday song that will stay in people’s heads and pad the bank account of the author for the rest of their life.

Sadly, it’s why there are so many really objectively bad holiday songs, leading many to dislike the season’s music outright.

But like all genre’s holiday music has some of the finest tunes ever written and performed. So each year, I point to some offerings of some of the finest music of the season.

My expertise is based on collecting nearly 8,000 holiday songs and more than 3,000 albums of Christmas music. It has been a lifelong passion.

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 many of 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, some of which are far from complete.

Many of these included in this story can be found streaming services or various sites online.

This list of holiday music is fairly comprehensive, but most 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 artist covers of classic holiday music (there are a few exceptions) pale in comparison to the rich arrangements and musicians who made the originals special. Copying vocal licks or trying to make the sound of a classic Christmas tune “more modern” rarely works.

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

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.

These records are divided 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.

Instrumental/Jazz

“An Oscar Peterson Christmas” - Oscar Peterson

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

“Silent Nights” - Chet Baker

Another compilation of one of our finest trumpet players holiday music. Surprisingly 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 jazz 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 fine guitar album of a mix of holiday hits. Underrated guitar wizard.

“Christmas with Doyle Dykes,” Doyle Dykes. One of the greatest living fingerpickers, Dykes guitar sings Christmas songs with depth and joy.

“Winter Nights,” Al Di Meola. Quirky, with fewer familiar tunes, the speedy guitar of Di Meola carries the holiday spirit.

“The Ventures Christmas album” - The Ventures Recorded in 1964, a surf music spin on the holidays. It grows a bit tiring with each cut, but is something different and fun.

“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 than piety. Also included in this reissue are six tracks from his 1975 release Christmas with John Fahey, Vol. II.

Vintage - Artists

“Ultimate Christmas,” Frank Sinatra 20 tracks, 15 of which fit the title of the compilation perfectly. “The Christmas Waltz” and “I’ll Be Home for Christmas” will light up any tree.

“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” are as good as things get. Also check out Ella’s “Ella Wishes You a Swingin’ Christmas” which has released an expanded version for this year.

“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, if a little stiff in spots.

“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,” at the end of the album, 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.

“A Jolly Christmas from Frank Sinatra,” Frank Sinatra

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.

Vintage - Compilations

Note: there are some crossover songs in these collections.

“The Most Fabulous Christmas Album Ever,” lousy title, great album. Glenn Miller/Tex Beneke “Jingle Bells (maybe the best, and weirdest version)” from 1941 kick off the album, which also features Vaughn Monroe’s “Let it Snow” (the definitive version), Charlie Spivak’s “What Are You Doing New Year’s Eve,” Claude Thornhill’s spectacular “Snowfall,” and solid cuts by Tommy Dorsey, The Fontane Sisters, Dinah Shore, and Perry Como. There are a couple of smaltzty cuts (Spike Jones), but all in all a great collection.

“From the Sony Vault: Christmas with the Big Bands,” is a gem. Most of the big band Christmas stuff is worth a listen, but this collection offers a great sampling with Artis Shaw’s “There’s Frost on the Moon,” Frankie Carle/Marjorie Hughes “Little Jack Frost Get Lost,” Tex Beneke’s “Sleigh Ride,” and a 14 other cuts to make the holidays happy.

“Christmas on the Bandstand,” another fine big band collection featuring Kay Kyser’s “Hello, Mr. Kringle,” Les Brown’s “When You Trim Your Christmas Tree,” and Harry James' “White Christmas,” along with nine other selections that are merry and bright.

“Swingin’ Christmas Party,” with Fats Waller’s “Winter Weather” and “Swingin’ Them Jingle Bells,” nd the very odd Art Carney rap holiday song from 1954, and nine other cuts (again, some of which are on the collections already noted).

“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

“A Very Swingin’ Basie Christmas” - The Count Basie Orchestra. Swell record to put on while decorating the tree or wrapping holiday gifts.

“The Classic Big Band Christmas Album,” with Eddy Duchin’s “Don’t Wait for the Night Before Christmas,” Charlie Spivak’s “A Wonderful Winter,” and other favorites.

“Jingle Bell Swing,” where Miles Davis “Blue Xmas (To Whom It May Concern),” Duke Ellington’s “Sugar Rum Cherry (hip arrangement of “Dance of the Sugar Plum Fairy) head a chill but upbeat holiday collection of 14 songs.

“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 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 bring 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

“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.

Newer

“A Capitol Christmas,” with many holiday favorites covered by the Beach Boys, Glenn Campbell, the Lettermen, Johnny Mercer, Lena Horne and more.

“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 source 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 should skip this one, but you are missing a little gem.

“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. Some arrangements are a little corny, but overall worth a listen.

“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 (re released as Christmas Cookin’)” - Jimmy Smith

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

“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,” VariousArtists

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