Many people enjoy the holiday spirit, family time, food, desserts, and other activities like holiday movies. There are classics like “This Christmas” and films like “Polar Express,” “The Grinch,” “Home Alone,” and others, but you also can experience new holiday movies that aid in the holiday experience. Ashlei Sharpe Chestnut stars in her new Max Christmas movie, “Mistletoe and Matrimony,” which began streaming on Dec. 14.
Chestnut stars as Olivia Morris, a Chicago wedding planner tasked with organizing her sister’s wedding, only to realize the best man is her ex-boyfriend, played by Etienne Maurice (founder of WalkGood LA). The festive film offers heartfelt holiday romance and laughs for the season.
“I’ve been wanting to do a Christmas movie for years now, and when I got the call and read the script, it was like everything I dreamed of,” Chestnut said as she described the feeling of getting the role of Olivia. “This movie brings a warm, family-like atmosphere for the holiday spirit.”
Chestnut acting career started in Charlotte, North Carolina, as she attended a performing arts middle and high school before moving to New York. Upon her move, she beagn began in theater, working on Broadway after having a tumultuous time looking for management. “In my senior year in college, we had a showcase in New York with agents and casting directors in attendance, and after my performance, I garnered agent interest, but because I wasn’t living in NY at the time, they instructed me to move there and once settled, call them.” Shortly after becoming a resident of NY, she called the agents and directors, but there was no answer, forcing her to improvise.
Chestnut started handing out resumes and headshots to every studio and agency that would take them. She attended a networking event held by the One On One agency, which put her face to face with industry professionals, leading her to book her first Broadway show without representation. Over time, and after starring in Tony-nominated productions such as “The Crucible” and “A Doll’s House Part II,” Chestnut took her talents to television after landing her first on-screen role on “Gotham” as Officer Parks. She has also starred in prominent movies/shows like “Star Trek: Picard” (Paramount+), “Cruel Summer” (Freeform), and “Gotham” (DC), with her currently portraying Naomi Howard on NBC’s “Chicago Med.”
“I try to find similarities with myself and the character when playing different roles on different shows regardless of the genre,” Chestnut said as she spoke about her diverse resume. “For my character in the movie, we are both school-oriented and driven, which made it easy to connect with Olivia.”
On Chicago Med, Chestnut plays Naomi Howard, a medical school student navigating her first clinical rotation in the emergency department. “I love playing Naomi because her character is the exact opposite of me. She’s more timid, shy, and scared to make mistakes, while I like making my presence known. Her character stretches my acting skills.”
You can catch up with all 10 seasons of “Chicago Med” on NBC, Hulu, and Peacock. Also, be on the lookout for Chestnut first directed movie in 2025.

