You know that feeling when a song starts and you immediately want to grab a peppermint stick and a giant glass of eggnog? That’s the power of the 1963 classic. Honestly, Andy Williams It’s the Holiday Season isn’t just a song; it’s a time machine. But there is a lot more to this track than just a crooner in a sweater.
Most people think it’s one single song. It’s not. It is actually a mashup—a "medley" if you want to be fancy—of two completely different songs written by two very different people.
The Kay Thompson Connection
The part of the song that goes "So hoop-de-do and dickory dock" was written by a woman named Kay Thompson. If that name sounds familiar, it’s probably because she wrote the Eloise books. Yeah, the ones about the mischievous kid living in the Plaza Hotel.
Kay was a powerhouse. She was a vocal coach at MGM, a mentor to Judy Garland, and, as it turns out, a bit of a secret weapon for Andy Williams. She actually wrote "The Holiday Season" back in 1945. For years, it kind of just sat there. It wasn't some massive hit.
Then came 1963.
Andy was putting together The Andy Williams Christmas Album. Kay, who was his close friend and mentor (and some biographers say they were more than that), decided to dust off her 1945 track. She didn't just give it to him, though. She helped arrange it to weave in and out of Irving Berlin’s "Happy Holiday."
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Why the Irving Berlin part matters
"Happy Holiday" was already a massive deal. It was written for the 1942 movie Holiday Inn and originally sung by Bing Crosby. By mixing Kay’s swingy, jazzy "Holiday Season" with Berlin’s traditional "Happy Holiday," Andy created something that felt both old and new at the same time.
That "Hoop-de-do" Lyric Explained
Let’s talk about the lyrics. They are weird.
- "Hoop-de-do and dickory dock."
- "Leave a peppermint stick for old St. Nick."
- "Don’t forget to hang up your sock."
It sounds like a nursery rhyme on espresso. That was Kay Thompson’s style. She loved rhythmic, punchy words that felt like they were dancing. When Andy Williams sings them, they sound effortless, but they’re actually pretty syncopated and tricky to time right with the orchestra.
Basically, the song is a giant checklist for a 1950s Christmas. You’ve got the snow, the chimney, the toys, and the peppermint sticks. It’s the "vibe" of Christmas condensed into about two minutes and fifteen seconds.
Why Andy Williams Owns the Season
He wasn't called "Mr. Christmas" for nothing. While the 1963 album is the gold standard, Andy’s TV specials are what really cemented this song in the American brain.
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Think about the set: fake snow, the Williams brothers in matching outfits, and those Osmond kids appearing out of nowhere. Andy Williams It’s the Holiday Season was often used as a big production number. It’s a "moving" song. It’s meant for walking down stairs or spinning a dance partner.
You can’t really sit still while listening to it.
The 2020s Resurgence
What’s wild is how well this song is doing now. In 2021, the medley actually re-entered the Billboard Hot 100, peaking at #18. Think about that. A song recorded during the Kennedy administration is still beating out modern pop stars every December.
It’s the nostalgia. People are tired of everything being digital and sleek. They want the warmth of a Robert Mersey orchestration. They want to hear a guy who sounds like he’s actually happy to be singing about socks.
Getting the Most Out of the Track
If you’re building a holiday playlist, you’ve gotta be careful which version you pick. There are live versions from his Branson, Missouri years, but the 1963 studio recording is the one you want.
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The mix of the brass section and those crisp backing vocals is what gives it that "Discovery Channel" crispness.
Pro tip: Listen for the transition. The way it slides from "Happy Holiday" into the first "It's the holiday season" is a masterclass in mid-century arranging. It doesn't bump; it flows.
To really appreciate the history of the song, try listening to Kay Thompson’s original 1945 version if you can find it. It’s much more "theater" and less "fireplace," but you can hear the bones of what Andy eventually turned into a masterpiece.
Now, go find some peppermint sticks. You've got a playlist to update.
Actionable Next Steps:
- Check your playlist: Make sure you have the 1963 version from The Andy Williams Christmas Album (the one with the red cover).
- Watch the 1971 TV Special: Search YouTube for Andy singing this with the Williams Brothers and the Osmonds to see the choreography Kay Thompson originally envisioned.
- Read the Credits: Take a second to look for Kay Thompson’s name on the track list—she’s the unsung hero behind the "hoop-de-do."