The goal of A Gil Brentley Christmas was to extend the narrative world of Maybe Happy Ending by transforming an existing emotional touchpoint from the show into a seasonal cultural moment. Rather than creating a standalone holiday song, the campaign reimagined “Then I Can Let You Go” (a musical number from the production) as a Christmas jazz recording, developed in collaboration with the original creators of the musical to preserve its emotional integrity.
The video featured actor Dez Duron performing the holiday arrangement as a contemporary embodiment of his fictional character "Gil Brentley", the 1950's jazz crooner referenced within the musical. This approach allowed the activation to blur the boundary between fiction and reality, positioning the musical’s world as something audiences could encounter beyond the theater.
Visually and tonally, the piece leaned into classic holiday jazz aesthetics while maintaining the retro-futuristic atmosphere of Maybe Happy Ending. Presenting the recording as a cultural artifact rather than promotional content enabled audiences to engage with the music organically, experiencing the story’s emotional landscape through a familiar seasonal lens.
By transforming a core musical theme into a holiday narrative extension, the campaign turned a traditional marketing window into an opportunity for immersive world-building and long-term audience connection.
The music video drove strong organic engagement by functioning as standalone entertainment while simultaneously deepening audience familiarity with the show’s score. Its cross-platform distribution expanded reach beyond typical theater marketing channels, connecting with both holiday music listeners and jazz-focused digital communities.
Collaborating with the original songwriters reinforced authenticity, strengthening audience trust while enhancing the perception of the musical as a fully realized narrative universe. Instead of operating as a short-term promotional beat, the strategy positioned the content as a lasting cultural extension of the show’s world, building sustained affinity and emotional resonance.
The first video of "Then I Can Let You Go" was picked for a press exclusive by the outlet Playbill. The activation gained over 660K Impressions across platforms.