In late 2015, Ariana Grande‘s seemingly frictionless ascendance to all-consuming pop superstardom had finally hit a tiny bit of turbulence. “Donutgate” and other small-scale controversies had put her in the media’s crossfire for the first time, while “Focus” — the planned lead single off her upcoming third album, then to be titled Moonlight — had disappointed commercially and left fans a little cold. It was nothing she couldn’t and wouldn’t bounce back from, but in the meantime, she dropped a surprise release to celebrate the holiday season, and give both her sound and her career a little bit of a reset: the six-song EP Christmas & Chill.

On this week’s Great Moments in Pop Star History episode of the Greatest Pop Stars podcast, host Andrew Unterberger is joined by Billboard staff writer and longtime Arianator Kyle Denis to look back at 10 years of Christmas & Chill. We remember the Ariana Grande holiday releases that preceded it — including a song that’s already well on its way to being an all-time seasonal standard — and then dive into why Chill has come to hold a particularly special place in the hearts of fans and of Grande herself, as well as how it ended up predicting a lot of the places she would go in her later secular releases.

While doing so, we address all the most pressing questions around Grande’s Christmas & Chill — how did an EP with no self-consciously big songs on it end up playing such a big part in her career? What are our favorite songs on the EP? How did she get away with a ukulele song in 2015? Do we care about the difference between the “Naughty” and nice versions of “Santa Tell Me”? Why has Grande never made much of an effort to actively revisit or repromote any of her holiday releases? And perhaps most importantly: Is there a world in which Grande eventually ends up being Mariah Carey’s successor as the Queen of Christmas?

Check it out above — along with a YouTube playlist of some of Ariana’s most relevant holiday music moments, all of which are discussed in the podcast — and subscribe to the Greatest Pop Stars podcast on Apple Music or Spotify (or wherever you get your podcasts) for weekly discussions every Thursday about all things related to pop stardom!

Also check out Kyle’s 2025 Year in R&B review, as well as his recent Druski cover story.

And as we say in every one of these GPS podcast posts — if you have the time and money to spare, please consider donating to any of these causes in the fight for trans rights:

Transgender Law Center

Trans Lifeline

Destination Tomorrow

Gender-Affirming Care Fundraising on GoFundMe