Ashlei Sharpe Chestnut, widely recognized for her dynamic performances in Rap Sh!t and Star Trek: Picard, is making her debut as a lead in a holiday romance with Mistletoe and Matrimony. In a candid interview, Chestnut reflected on her artistic journey, her connection to the film’s character, and the importance of Black representation in holiday storytelling.
The actress began her career immersed in theater, attending a performing arts middle and high school before earning her BFA in acting. After graduating, she landed her Broadway debut in The Crucible, a milestone that paved her way to television and film roles. Though her career has transitioned to television and film, Chestnut expressed her deep appreciation for the immediacy and intimacy of live theater. She shared that she would eagerly return to the stage, calling it “a cornerstone of her artistry.”
For Mistletoe and Matrimony, Chestnut takes on the role of Olivia, a driven wedding planner balancing the chaos of holiday nuptials with her own personal journey. The film, which streams December 14th on OWN and Max, marks a career milestone for Chestnut, as leading a Christmas movie was a longtime goal of hers. Describing her preparation for the role, she shared how Olivia’s family-oriented, perfectionist nature resonated with her own personality.
The cast and director’s off-screen camaraderie was another highlight of the production, with Chestnut recounting bonding moments like a group trip to Niagara Falls. She credits these experiences for the palpable on-screen chemistry between the characters.
Chestnut also hinted at the potential for a sequel, noting that the film’s ending leaves room for more storytelling as Olivia’s next challenge could involve planning her own wedding.
When discussing the broader impact of Mistletoe and Matrimony, Chestnut emphasized the importance of authentic Black representation in holiday films. By showcasing nuanced love stories featuring darker-skinned actors in joyful and relatable narratives, the film contributes to a shift in how Black love is portrayed on screen. Chestnut hopes such stories inspire younger audiences to see themselves reflected in beautiful, aspirational ways.
Mistletoe and Matrimony, directed by Rhonda Freeman-Baraka and also starring Etienne Maurice premieres Saturday, December 14 on OWN and Max, watch the full interview with our correspondent Jianna Ewuresi below.