The Sound of Christmas: A Spin Through Holiday Album History
Before you could pull up a Christmas playlist on your phone, the holidays had a soundtrack you could actually hold in your hands. Think vinyl records with glossy covers: Jo Stafford curled up by the fire and reading, Frank Sinatra looking sharp in a tux, orchestras shimmering in white tie and tails.
From the 1940s through the 1970s, a good holiday album was as essential as a tree with tinsel or a family Christmas punch recipe. This was the sound of cozy living rooms, postwar optimism, and a little Hollywood sparkle.
The Song That Started It All (Yes, That One)
Of course, it all kicked off with Bing. He literally started the genre of holiday music.
When he sang “White Christmas” in 1942 (in Holiday Inn), it wasn’t just a hit. It was a phenomenon. The world was at war and the song offered comfort to our soldiers far from home and families waiting for their return. Bing Crosby’s voice, warm and effortless, defined what Christmas music would sound like for generations: sentimental, elegant, and undeniably American.
The single sold an insane number of copies (still the best-selling single ever, by the way), and it kicked off a whole tradition of holiday albums.
His Merry Christmas album came out in 1945 and reissued about a million times, became the blueprint. It had the perfect mix of traditional carols and those sweet, nostalgic songs we all know. Bing had this way of making Christmas feel less like a date on the calendar and more like a warm feeling you could replay whenever you needed it.
The Crooner Era: Sinatra, Cole, and Setting the Standard
By the '50s, this whole Christmas album thing was really taking off. Frank Sinatra came out with A Jolly Christmas from Frank Sinatra in 1957 (go right now and listen to his swinging version of Jingle Bells. We’ll wait), that included those lush string arrangements from Gordon Jenkins. Frank had a knack for sounding both larger-than-life and deeply personal. He was like a department store’s holiday window, showcasing gifts everyone craved, but also that one perfect present meant just for you. He could make you feel both alone and cozy at the same time.
Then came Nat King Cole’s The Magic of Christmas (1960), home to the timeless “The Christmas Song (Chestnuts Roasting on an Open Fire).” Cole’s voice radiates warmth; his phrasing makes every line feel effortless and eternal. The record became such a part of the American holiday soundscape that it’s impossible to imagine Christmas without it.
Swinging Through the Season: Ella Brings the Joy
And then there was Ella.
Ella Wishes You a Swinging Christmas (1960) is just pure fun. While Bing crooned wistfully and Frank brooded stylishly, Ella laughed and joked. Her versions of “Jingle Bells” and “Sleigh Ride” are pure joy. She proved you could be sophisticated and have a blast at the same time.
Backed by the Frank DeVol Orchestra, she gave the holidays a big-band glow that was equal parts swanky and fun. In a decade of rapid change (new suburbs, TV dinners, and big cars) Ella reminded everyone that elegance could still swing.
Holiday Duets and Dynamic Duos
The '60s also gave us a gem that doesn't always get enough love: That Holiday Feeling! (1964) by Steve Lawrence and Eydie Gormé. This husband-and-wife duo had incredible chemistry, and their album feels like the best holiday party you've ever been to, caught on record. Their harmonies are tight, the arrangements are sleek, and songs like "Let It Snow!" sparkle with mid-century cheer. It’s pure '60s vibe, when Christmas meant TV specials, the Sears Wish Book, and aluminum trees. Put this one on and you'll want to pour yourself an eggnog and start decorating with tinsel.
Orchestras, Brass, and Going Big
While the singers gave Christmas its voice, the orchestras gave it grandeur. The Glenn Miller Orchestra carried their founder’s swing legacy into the season with In the Christmas Mood, bringing dance-floor energy to familiar carols. Their takes on “Jingle Bells” and “Winter Wonderland” feel like a time capsule from the USO shows and ballrooms of the 1940s.
They had good company: The Boston Pops under Arthur Fiedler, Percy Faith and His Orchestra, and The Ray Conniff Singers (“We Need a Little Christmas!”) all released holiday albums that filled living rooms with orchestral sparkle. These records weren’t background music. They were the atmosphere, competing only with the television yule log for living room ambiance.
The Velvet Touch of Johnny Mathis
If Bing was comfort and Frank was sophistication, Johnny Mathis was pure romance.
His Merry Christmas (1958), complete with that iconic cover of Mathis in the snow, became a seasonal favorite that never went out of style. His smooth tenor glides through “Winter Wonderland” and “Sleigh Ride” with effortless charm. He'd go on to make more Christmas albums. But that first one? Still one of the all-time greats. It's like a mid-century Christmas card coming to life through your speakers.
The Pop Era and Beyond
By midcentury, Christmas albums were everywhere. Who can forget Elvis and the Jordanaires (1957) with their version of “Blue Christmas” or The Andy Williams Christmas Album (1963) with "It's the Most Wonderful Time of the Year"? These records captured mid-century American optimism at its most polished: festive, hopeful, and perfectly produced.
Even as rock and pop dominated the charts, that crooner-era warmth never faded. The Carpenters' Christmas Portrait (1978) carried the torch into the late '70s, with Karen Carpenter's voice channeling all that earlier elegance and heart.
Today, artists like Michael Bublé, Norah Jones, and Harry Connick Jr. still tap into that timeless style, proving that a touch of swing and sentiment will always belong to Christmas.
The Legacy Continues (And Gets a Fresh Spin)
The golden age of the holiday album may belong to the past, but its spirit is alive and well. Listening now is like stepping back in time: you can almost hear the TV Christmas specials, the neighborhood carolers, and the rustle of wrapping paper (to be folded and used again next year). 
And that tradition of holiday music? It's still going strong with the addition to this storied catalog: Swinging In The Holidays. This debut album from Songbook Ink features fresh, memorable tracks performed by top musicians and liner notes by jazz legend Ken Peplowski. It honors those golden-era classics while creating something that feels alive, current, and worthy of a spin on your turntable (or, let's be real, your meticulously curated Spotify playlist).