In late 2015, pop superstar Ariana Grande navigated a period of minor turbulence in her otherwise smooth career ascension. Following controversies like "Donutgate" and the commercially disappointing lead single "Focus" from her then-upcoming third album, 'Moonlight', Grande released a surprise six-song EP titled 'Christmas & Chill'. This release served as a strategic move to reset both her sound and her career trajectory during the holiday season.

The significance of 'Christmas & Chill' ten years later was recently explored on the "Great Moments in Pop Star History" episode of the 'Greatest Pop Stars' podcast. Host Andrew Unterberger, joined by Billboard staff writer and longtime Arianator Kyle Denis, delved into the EP's enduring appeal. The discussion recalled Grande's earlier holiday releases, including "Santa Tell Me," a track already on its way to becoming an all-time seasonal standard.

The podcast episode highlighted why 'Christmas & Chill' holds a particularly special place in the hearts of both fans and Grande herself. It also examined how the EP, despite containing no self-consciously "big" songs, remarkably predicted many stylistic and thematic directions Grande would take in her later secular music. Pressing questions addressed during the conversation included: the EP's outsized role in her career, favorite songs from the collection, the boldness of a ukulele song in 2015, the nuances between "Naughty" and "nice" versions of "Santa Tell Me," and Grande's apparent lack of effort to actively revisit or re-promote her holiday releases.

Perhaps one of the most intriguing questions discussed was whether Grande could eventually succeed Mariah Carey as the "Queen of Christmas." The comprehensive look back at 'Christmas & Chill' underscored its critical role in Grande's artistic evolution and its unexpected impact on her journey to solidified pop superstardom.