The Observer’s Best Holiday Music List is Here Just in Time
Greg Wilson/Anderson Observer
Christmas is back, and with it the annual onslaught of holiday music that seems to seep into every aisle, lobby and radio preset long before the turkey leftovers are gone. For some, those familiar sleigh bells are a welcome soundtrack; for others, they’re a seasonal tax on patience and good will.
Count this listener in the first camp, at least in theory. A personal archive of more than 13,500 pre-1970 Christmas recordings suggest no shortage of affection for the genre’s deep cuts and vanished crooners. Yet it is hard to fault the skeptics when so much of what pipes through stores and streaming playlists in December is thin, overproduced and aggressively unimaginative.
Every year, a fresh crop of artists dutifully turns out hammy versions of the same dozen standards, or tries to mint a new classic with lyrics and melodies engineered for gift-shop rotation. The result often feels less like tradition than like brand management set to a jingling beat. Still, buried beneath the churn is a trove of recordings—many from more than six decades ago, others from modern jazz and soul players—that reward anyone willing to dig past the usual fare.
Thanks to streaming platforms, most of that music is only a search away, whether your allegiance lies with (in order of preference, I have them all) Spotify, Pandora, YouTube Music, Apple Music, Tidal or Amazon’s service. For listeners who have nearly surrendered to the idea that all Christmas music sounds the same, there remain albums for almost every mood that can soften even the most hardened seasonal skeptic.
My tastes in holiday music are fairly comprehensive, with the exception of the novelty Christmas songs, none of which hold up well in any era, including the silly attempt at religious kitsch of the abominable “Little Drummer Boy.”
While the 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 to 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 collections that include or feature any of the big band singers or crooners from the late 1930s-early 1960s and you will find a lot of music to enjoy. Bing Crosby, Frank Sinatra, Ella Fitzgerald, Dinah Shore, Rosemary Clooney, Kay Starr, Dean Martin, etc., deliver and the live orchestras that accompany them sweeten the sound.
Here are a few to sample:
“Christmas Songs by Sinatra” – Frank Sinatra
Recorded in 1948 with a mixture of sacred and secular Christmas music, this one hits a bullseye. “Christmas Dreaming” is as good as it gets, and the “Christmas Carol Medley,” a cut from the “The Guest Star” radio series, always brings big smiles at my house.
“Merry Christmas” - Bing Crosby
Originally released as a 10-inch EP in 1948, this full album of songs by Bing, the man who taught the world how to properly use a microphone, is at his best in the collection of traditional Christmas favorites released in this incarnation in 1955.
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.
“Snowfall” - Tony Bennett
From 1968, A good holiday showcase od runway from a young 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.
“Christmas Carousel” – Peggy Lee
From 1960, these 12 songs pepper in a few lesser-known tunes and Lee’s voice was made for eggnog season.
“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 joyful Christmas 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 though a little lackluster in the arrangements, 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.
“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 when “Old Blue Eyes” was in his prime.
“Christmas Portrait,” – The Carpenters
Released in 1978, sold in the seven figures and quietly took up residence in the living rooms and cul-de-sacs of North American suburbia, where it has spent decades politely jousting with Anne Murray for seasonal supremacy. The 1984, two-disc expansion only intensified the effect, turning the record into a kind of blizzard of carefully managed cheer, dense with strings, choir voices and an almost unblinking optimism. The material seems uncannily engineered for Karen Carpenter, whose cool, unforced alto wraps itself around “Sleigh Ride” and “What Are You Doing New Year’s Eve?” with the ease of a favorite winter sweater. The result is less a Christmas party than a meticulously decorated seasonal tableau—half comfort, half faintly eerie perfection.
“This Time of Year” – June Christie
From 1962, it consists entirely of original songs, unusual for its time. The recordings bear a similarity of having a melancholy tone to the album, all composed by the husband-and-wife songwriting team of Connie Pearce and Arnold Miller.
“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 for the ages.
“Christmas” – The Singers Unlimited/Leader: Gene Puerung
Maybe the best caroling album of holiday favorites. Recorded in 1971, every a capella group needs 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 and fun.
“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 with family and friends - including Emmylou Harris, Rufus Wainwright, Martha Wainwright and Beth Orton – this was the last recording before Kate’s death. It is a wonderful and unusual collection 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.
“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 a 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. This one grows on me more every year, and that’s high praise since I liked it from first listen.
“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 "Santa Fly,” featuring Martin Mull and the Sondra Gaskin Glee Club, is as funky as the holiday gets.
“The Pianoman at Christmas” – Jamie Cullen
A bit over-the-top at times, but still a fun sleigh ride of traditional tunes.
“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.
“The Twenty-Fifth Day Of December” - The Staple Singers
From 1962, it’s everything you would expect from this group, the album contains 12 holiday and spiritual classics including "Joy To The World," "Silent Night" and "Go Tell It on the Mountain." Included also is their treatment of the Rev. Thomas Dorsey’s "The Savior Is Born." The album delves deep into traditional spirituals such as "The Virgin Mary Had One Son," "Wasn’t That a Mighty Day" and "Last Month of the Year" and includes an original by group founder Roebuck "Pops" Staples titled "There Was a Star."
“That Holiday Feeling!” - Steve Lawrence and Eydie Gormé
Backed by swinging Don Costa arrangements, this 1964 set is the Christmas album many Sinatra fans wish he’d recorded. Lawrence and Gormé shine on solo features, but the real magic comes when they team up on “Winter Wonderland,” “Santa Claus Is Comin’ to Town” and a roaring “Sleigh Ride.” The big band, strings and unabashedly flirty title track deliver peak holiday cheese—in the best possible way.
“Christmas with the Everly Brothers and the Boystown Choir”
This 1962 album by The Everly Brothers, includes the 33-member Boys Town Choir and the Boys Town organ in Omaha, Nebraska. Two songs, "Away in a Manger" and "Angels from the Realms of Glory," are sung entirely by the choir. Don Everly performs "What Child Is This?" solo and Phil "O Little Town of Bethlehem."
“Tinsel and Lights” – Tracey Thorn
The album mostly avoids canonical Christmas songs, but instead features covers of songs by Sufjan Stevens, Joni Mitchell, Randy Newman, Ron Sexsmith and the White Stripes as well as self-penned songs. Scritti Politti's Green Gartside features on a cover of Low's "Taking Down the Tree", as well as writing "Snow in Sun". Ben Watt, who is Thorn's husband and partner in Everything but the Girl, plays on most tracks, and their three children provide backing vocals on the track "Joy".
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. The fist cut, “God Rest Ye Merry Gentlemen,” features a smooth bass carrying the melody.
“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 and great music.
“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 the iconic “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 than piety. Also included in this reissue are six tracks from his 1975 release Christmas with John Fahey, Vol. II.
“Silent Nights” - Chet Baker
Superior 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 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 60 years.
“Six-String Santa” - Joe Pass
Joe Pass, perhaps the best guitar player of my generation, could not be better in his cover of these Christmas tunes. The songs are familiar, but he adds holiday flavors.
“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 weird fun all the way through. If you love Tuba Music, this is for you.
“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 guitarist brings a smooth, but never dull, vibe to seasonal favorites.
“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.
“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 takes on “Oh Come, All Ye Faithful” and the keyboard work in “Angels in the Snow” are the most memorable cuts.
“Grants Department Store: Albums 1-8 / A Very Merry Christmas” – YouTube
This eight-album set of a mix of instrumental and vocal Christmas music (including some rarities by Bing Crosby) is the perfect soundtrack to any holiday event, from trimming the tree to opening presents to after-dinner chill. I am listening to it as I write this column. Available only on YouTube.
Copyright © 2025, Anderson Observer Publisher. All rights reserved.
