In 2008, singer/songwriters Sara Bareilles and Ingrid Michaelson collaborated on an original song entitled "Winter Song" for a Christmas album, The Hotel Cafe Presents Wintersongs, a compilation of originals and traditional holiday songs performed by a line-up of female artists. Both artists had had success in the two years prior, especially Bareilles, who had had massive success with her major label album Little Voices in 2017. While Michaelson was purposely more underground, she had a huge fan base as well. "Winter Song" was released to very little fan-fare, surprisingly, but then suddenly became a huge hit in Ireland, where it went to #2.

The sudden spotlight on the song resulted in unplanned duet performances by Bareilles and Michaelson, including on The Tonight Show and for the Obamas at the 2010 US National Christmas Tree Lighting. In Ireland, a large choir recorded a version of the song that was sold with all proceeds benefitting a local charity, and the song has been covered by disparate musical luminaries on their own Christmas records, including John Legend, Rob Halford (from metal band Judas Priest), and Hamilton's Leslie Odom, Jr. It has also been played on TV shows Scrubs and Grey's Anatomy, as well, and has generally become part of the modern holiday canon. Bareilles and Michaelson, meanwhile, have continued their own successful careers and have now separately appeared on Broadway, with Bareilles being nominated for a Tony award for her musical score of the 2016 musical Waitress and Michaelson temporarily playing a key role alongside Josh Groban in the critically applauded Natasha, Pierre & The Great Comet of 1812. Even with their busy careers, it seems like only a matter of time before the two will re-unite for a performance of their holiday classic some December.