By the time most people are taking down their Halloween decorations, Ingrid Michaelson is already three Christmas movies deep and halfway through wrapping “hundreds” of presents. “I start watching Christmas movies in September,” she admitted, absolutely unbothered. Thanksgiving, in her world, is “basically the little sister of Christmas.” The woman is not playing around.
So when she finally made a holiday record, she wasn’t going to toss off some jingle-bell side project between tours. Songs for the Season had to feel like it’d been in your family’s milk-crate of vinyl for 40 years. The cover is all retro fonts and soft-focus mood, and the music leans even harder into the fantasy: “Frank Sinatra and Nat King Cole and Judy Garland and the Peanuts Charlie Brown Christmas,” she said. “I wanted something that felt older.”
The key word she kept beating into everyone’s head was nostalgia. “It just has to be nostalgic,” she told her producers Saul Simon MacWilliams and Dan Romer. “It has to leave people feeling like they’ve heard this before.” That wasn’t just about song choice, it was in the gear, the mics, and the way they tracked everything. “We used technology of today,” she said, “but tried our best to implement techniques from the ’50s” — live orchestra instead of copy-paste strings, woodwinds that actually breathe, vocal filters that sound like they remember mono.
You can really hear it on “New Year’s Eve,” where the strings don’t just swell, they sort of ooze into view, and on the one original, “Happy Happy Christmas,” where the nostalgia drops its cozy sweater and shows its teeth. “It’s a sad song, but it’s also a hopeful song,” she said. “I wrote it about my mother who passed away three years ago.”
Michaelson grew up in a big old Victorian house on Staten Island, tall ceilings, giant tree, half-Swedish family, and an annual Christmas Eve party where the neighborhood basically invaded. “There’d be 50, 60, 70 people,” she remembered. “My dad would be playing piano, everybody singing carols, people bringing food, Swedish meatballs… it was very filled with traditions.” For someone hard-wired to find comfort in repetition — same house, same boxes, same wreath on the same door — Christmas is the mother of all rituals. Which makes it pretty cruel when your actual mother is gone.
“I didn’t want to gloss over people’s pain and people’s loss,” she said. “Every year there are these tent poles in our life, and they bring good memories and sad memories.” “Happy Happy Christmas” sits right in the middle of that. The song is about understanding that the season hurts and still insisting on light anyway. “I know my mother wouldn’t want me to lose my childlike wonder,” she said. “She’d want me to have a happy Christmas. She’d want me to keep that spirit alive.”
If that sounds like a lot for a holiday album, well, the great ones always sneaked in a little ache. Michaelson knows that too. “The best Christmas albums carry that balance of joyfulness and melancholy,” she said. She also knows the other side of the game: evergreen money. “We call it evergreen because it never goes away,” she laughed. “It comes back every year.” She’s fully aware that Mariah Carey basically broke the system with “All I Want for Christmas Is You.” “That’s one of the hugest songs, period,” she said. “Every year you see it on the charts and there it is again.”
Michaelson covers it on Songs for the Season, but drags it into a much sadder, more longing place. “I really mined the sadness and the longing in that song,” she said. “We tried to take this modern song and pull it back into that older world.” It’s probably not replacing the original at the mall, but that’s not the point; she’s aiming for something else — the record you put on at midnight when you’re honest.
Of course, this is still the music industry, so she’s already thinking deluxe edition. “Everybody’s got a deluxe,” she joked. “So next year I guess I’ll just resurface it.” But she also knows this is probably the Christmas album, singular. “This is the one,” she said. “I probably won’t make another one, although I might have a deluxe next year,” she added, not fooling anybody.
The moment that really got to her was a message from a fan who sent a video of her little daughter spinning around the living room with the record on. “‘This is going to be Casey’s Christmas record she’ll grow up listening to,’” Michaelson recalled. “That made me almost cry. I had those records as a kid. The fact that I’m going to be part of people’s holidays… that’s extremely important and special to me.”
And because she apparently lives on nostalgia as a primary food group, the next album goes backward in time again, just to a different decade. “I’m working on a Stranger Things-inspired record,” she said. “It’s a different kind of nostalgia. It’s 1980s nostalgia as opposed to 1950s.” Some songs are more generally about what the show makes her feel; others are basically love letters to specific characters and plotlines. “Not so specific that if you haven’t seen it you’ll be lost,” she promised, “but if you do know, you’ll be like, ‘Oh, I get that.’”
She gave one example: a song called “Through the Christmas Lights,” which her boyfriend initially assumed was another song about her mom. It’s not. “It’s about Joyce,” she said, fully nerding out, “sitting in the closet talking to her son in the Upside Down through the Christmas lights.” The chorus line — “I’ll talk to you through the Christmas lights” — works as metaphor for loss if you want it to, but Michaelson delights in the fact that it’s also extremely literal Stranger Things canon.
So the Christmas record bleeds into the Stranger Things record, which loops back into Halloween, which feeds right back into Christmas again. Nostalgia, but make it a lifestyle brand. “You would think as an adult it would have dulled a little bit,” she said, “but because I’ve gone through a lot of loss, it’s actually never going away.”
Given the evidence — Victorian house, Swedish meatballs, Winona Ryder fan fiction, presents wrapped in November — you believe her.
Listen to the interview above and then check out some of the video below!
