You know that feeling when you're in a grocery store in mid-November and suddenly, those bright, brassy horns kick in? The ones that sound like a 1960s TV special exploding into your ears? That's the moment you realize the "Christmas Creep" has officially won. And honestly, I’m not even mad about it. We are talking about the quintessential medley, It's the Holiday Season Andy Williams style—a track that has somehow managed to stay fresh for over sixty years without losing an ounce of its "hoop-dee-doo" energy.
It’s weirdly addictive. One second you’re humming along to a standard Irving Berlin tune, and the next, you’re singing about dickory docks and peppermint sticks. But there's a lot more to this song than just Santa coming down the chimney. It’s a masterclass in mid-century arrangement and a testament to the weird, wonderful genius of a woman named Kay Thompson.
The Secret Ingredient: Kay Thompson’s Fingerprints
Most people think this is just a single song. It isn't. It’s a "mashup" before that was even a word. The track officially titled "Happy Holiday / The Holiday Season" is a blend of two very different worlds.
First, you’ve got "Happy Holiday." That’s the Irving Berlin classic. He wrote it for the 1942 film Holiday Inn. You know, the one where Bing Crosby sings "White Christmas"? Interestingly, in the movie, they actually sing "Happy Holiday" on New Year’s Eve, not Christmas.
Then enters Kay Thompson.
If you don’t know Kay, she was basically the coolest person in Hollywood for three decades. She was a vocal coach for Judy Garland, she wrote the Eloise books, and she was Andy Williams’ mentor and, for a time, his lover. In 1945, she wrote "The Holiday Season." She had this frantic, jazzy, sophisticated style that just didn't sound like anything else on the radio.
When Andy went to record The Andy Williams Christmas Album in 1963, Kay was right there. She’s the one who suggested pairing her eccentric, fast-paced song with Berlin’s more traditional melody. The result? Pure gold. Without Kay’s "hoop-dee-doo and dickory dock," the song would just be another slow-burning carol. Instead, it’s a rhythmic rollercoaster.
Why 1963 Was the Year Everything Changed
It’s easy to forget how massive Andy Williams was. Before he was the guy your grandmother listened to, he was a chart-topping powerhouse. By the time It's the Holiday Season Andy Williams hit the airwaves, he was already a TV staple.
The album was recorded between September 9 and 13, 1963. Think about that. They were in a studio in Los Angeles, probably sweating in the late summer heat, trying to channel "Christmas snow white on the ground."
- The Voice: Andy had this "velvet" tone. He didn't oversing. He just glided.
- The Timing: The 1960s were the peak of the "Variety Show" era. Every December, families huddled around the tube to see the Williams brothers in their matching sweaters.
- The Arrangement: Marty Paich. That’s the name you need to remember. He arranged the track. He took Kay’s frantic energy and made it swing.
Funny enough, the record label (Columbia) didn’t think "It’s the Most Wonderful Time of the Year" was going to be the big hit. They actually pushed his cover of "White Christmas" as the lead single. They were wrong. The public gravitated toward the high-energy tracks, specifically the medley we're talking about today. It felt modern. It felt like a party.
Breaking Down the Lyrics: What is a Hoop-Dee-Doo?
Let’s get real. Some of these lyrics are straight-up bizarre.
"So hoop-dee-doo and dickory dock, and don't forget to hang up your sock!"
What is a hoop-dee-doo? Honestly, it’s just nonsense. It’s onomatopoeia for "having a good time." Kay Thompson loved using these percussive, silly syllables to keep the rhythm moving. It’s part of that "Vocal Punch" style she pioneered at MGM.
And then there's the "peppermint stick for old Saint Nick hanging on the Christmas tree." It paints this very specific, 1940s-style Christmas imagery. It’s nostalgic but also slightly manic. The song moves at a clip of about 120 beats per minute, which is faster than most Christmas songs. Most carols are designed to make you feel sleepy and warm. This one is designed to make you finish your holiday shopping in record time.
The "Mr. Christmas" Legacy
Because of this album, Andy Williams became "Mr. Christmas." He didn't just record one album; he recorded eight of them over his career. But the 1963 original is the one that stays on the Billboard charts every single year.
It’s actually fascinating to look at the data. In 2024 and 2025, Andy’s streams spiked higher than they did in the 70s. Why? Because It's the Holiday Season Andy Williams is a staple on "Coffee Shop Jazz" and "Classic Christmas" playlists on Spotify. It’s the ultimate "safe" song—it’s upbeat enough for a party but classic enough for a formal dinner.
Is It Better Than "Wonderful Time of the Year"?
This is the big debate among Christmas music nerds. "It’s the Most Wonderful Time of the Year" is technically the bigger hit. It’s the one everyone knows the words to. But "Happy Holiday / The Holiday Season" is arguably the better performance.
It requires more breath control. It has more complex harmonies (shoutout to the Williams Brothers who often backed him up). And frankly, it’s less overplayed. When you hear the "Happy Holiday" opening, it still feels like a surprise.
How to Listen Like a Pro This Year
If you want to really appreciate what’s happening in this track, try these three things next time it comes on:
- Listen to the bassline: It’s a walking jazz bass that never stops. It’s the engine of the song.
- Focus on the transition: Notice how seamlessly the song shifts from the 4/4 swing of "Happy Holiday" into the staccato "It's the holiday season" section. That’s the Marty Paich magic.
- Check out the 1963 TV footage: Go find the clip of Andy performing this on his show. He’s usually surrounded by dancers or his family, and you can see how much the rhythm of the song dictated the choreography of that era.
The truth is, It's the Holiday Season Andy Williams isn't just a song; it's a time capsule. It captures a moment when Christmas was about big orchestras, Technicolor TV specials, and the belief that a peppermint stick could solve most of your problems. Even if we’re living in a world of digital streaming and AI, that three-minute burst of brass and velvet still feels like home.
The best way to enjoy it? Turn it up way too loud while you’re decorating. It’s literally what Kay Thompson would have wanted.
To get the full experience, track down a vinyl copy of the original 1963 Columbia release; the analog warmth makes those horns sound much less piercing and a whole lot more festive. Once you've got the music set, grab some actual peppermint sticks—not the cheap plastic-wrapped ones, but the thick, old-fashioned kind—to hang on your tree just like the lyrics suggest.