Today was pure music-nerd joy. Stewart Mason — music writer, Medium legend, and all-around mensch — joined us for a gloriously chaotic, deeply opinionated romp through the world of Christmas songs. And yes, we went long.
We kicked things off with his controversial hill to die on: Paul McCartney’s “Wonderful Christmastime” is actually an excellent Christmas song.
Why Paul McCartney’s “Wonderful Christmastime” Is Awesome
Ed note: Stewart Mason wrote this story for Three Imaginary Girls last year, and it completely changed how I feel about this song*—so I asked him if we could run it on genXy, and he graciously agreed. We’re going to be talking about Christmas songs we love and hate (or love to hate) tomorrow (Dec 13) on
And honestly? He made the case.
Stewart broke it down: the synth-pop production, the monophonic analog weirdness, the cheerfully stoned energy of 1979 Paul messing with every button in his studio, and the utter lack of irony. We even learned the “creepy children’s choir” in the bridge is just Paul overdubbed and pitch-shifted — which somehow made it better (and yes, also a little weirder).
From there, we dove straight into:
🎶 Last Christmas — Wham!
Stewart: Thumbs up.
Dana: Enthusiastically yes — it’s karaoke canon.
Lawrence: Respectful appreciation.
We talked about the deceptively tricky melodic structure, Stuart’s commitment to the annual Whamageddon survival game, and the time Dana tried to karaoke it without knowing any of the verses. Spoiler: disaster.
🎶 “Happy Xmas (War Is Over)” — John & Yoko
Stuart does not like it.
Not because of the message — but because John Lennon wrote it in what Stuart believes was about 30 minutes. We learned:
Lennon’s solo catalog is… spotty. Yoko’s catalog is wildly underrated.
And Lawrence didn’t know the background vocals were literally singing “war is over.”
The things you learn at 55.
🎶 “All I Want for Christmas Is You” — Mariah Carey
The great divide.
Lawrence: loves it.
Stuart: respects the craft.
Dana: hates it.
We talked about the Phil Spector throwback structure, Mariah’s whistle register, and how Percy Jackson is now using it as a creature-banishing weapon. (Mariah, please don’t sue.)
🎶 “Christmas Wrapping” — The Waitresses
Dana’s all-time number one.
Stewart told us about his friendship with songwriter Chris Butler — and how he donates $500 in the first listener’s name each year when someone hears the song “out in the wild.” Dana melted.
🎶 “Do They Know It’s Christmas?” — Band Aid
A shared, conflicted yes.
Dana and Stewart both admit the truth: it’s a song you absolutely love while also knowing, line by line, it’s a colonialist fever dream (“Thank God it’s them instead of you” is… a choice). Stewart talked about how impressive the original Band Aid moment was, how much money it raised, and how it genuinely moved people at the time. Lawrence acknowledged the nostalgia factor while fully dragging the lyrical worldview.
Net take: problematic as hell, but historically undeniable — and still, somehow, a Christmas staple.
🎶 “Fairytale of New York” — The Pogues & Kirsty MacColl
Immediate, unanimous, full-body YES.
All three of us broke into collective GenX reverence for this one. Stewart gushed about Kirsty MacColl’s voice and phrasing, Dana swooned over the whole messy, gorgeous narrative, and Lawrence treated it like canon. It’s gritty, it’s mournful, it’s chaotic, it’s perfect — the anti–“Jingle Bells” anthem that somehow becomes more essential every year.
🎶 And yes — Wind Beneath My Wings
Not a Christmas song, but The Daily Whatever Show is nothing without side tangents. Today’s musical conversation devolved into a full-on breakdown of why the lyrics are objectively narcissistic, why Bette Midler is a goddess, and how Dana once tried to karaoke the entire thing. (Regrets.)
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It was chaotic, nerdy, joyful, mildly unhinged, and exactly the palate cleanser we needed after a week of relentless political doom.
A perfect December episode — and yes, we are building a community Christmas playlist now.
Stay tuned.
Thank you Dr. Mary M. Marshall, The One Minute Daily Boost, Rachel Hendricks, Jessica Bee 🍁, LeftieProf, and many others for tuning in. We love you, mean it!
