2025 NAACP Image Awards: 5 Times Morris Chestnut’s Onscreen Romances Had Us Rooting for Love
When it comes to Black love on the big screen, few actors have delivered more swoon-worthy moments than Morris Chestnut. With his signature charm, smooth delivery, and undeniable chemistry with his leading ladies, he’s given us couples to root for, cry over, and swoon after.
Whether he’s playing the devoted husband, the irresistible bachelor, or the man learning to love again, the veteran actor’s performances have stood the test of time.
His recent appearance at the 56th Annual NAACP Image Awards, hosted by Deon Cole, has us reminiscing about his most iconic roles. So, what better time to revisit those heartwarming moments? Time and again, Chestnut has proven he’s the ultimate romantic lead. So grab your tissues (and popcorn) as we relive his five most memorable onscreen romances.
Jackson and Denise / The Brothers
Chestnut played Jackson Smith, a successful physician with deep-seated commitment issues, in this fan-favorite film about love, friendship, and personal growth. Haunted by nightmares of a bride and struggling with emotional baggage, he turns to therapy, where his therapist encourages him to take a leap of faith and "give his heart to someone" for one night.
After making a strong connection with a woman he meets, Jackson finally opens up to the possibility of genuine commitment—until he discovers a shocking truth.
Chestnut’s portrayal of a man torn between his past and future makes this one of his most layered romantic performances.
Benjamin and Nancy / The Perfect Holiday
What’s more romantic than a holiday love story? Chestnut portrays Benjamin, an aspiring musician who steps in as a mall Santa and unknowingly wins the heart of a divorced mother, Nancy, played by Gabrielle Union. The two light up the screen with their chemistry as Benjamin becomes the man Nancy never expected but always needed. Watching him bond with her children while proving himself as a father figure made this feel-good film a Christmas classic.
Keith and Shanté / Two Can Pay That Game
When Shanté Smith, a confident career woman portrayed by Vivica A. Fox, suspects her boyfriend, Keith, played by Chestnut, of stepping out, she puts him through a ten-day strategy to bring him back in line. But when Keith flips the script and starts playing the game himself, their battle of wits turns into a hilarious showdown of love, pride, and power.
This film was peak early 2000s romance, and Chestnut was right in the center, showing us that sometimes, love is all about strategy.
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Ricky and Shanice / Boyz n the Hood
Though “Boyz n the Hood” is more of a coming-of-age drama than a love story, Ricky Baker(Chestnut) and his girlfriend Shanice, played by actress Alysia Rogers, portrayed young Black love in its purest form. Their relationship was built on dreams of a better future, with Ricky striving for a football scholarship to provide for their son. Their story, though tragically cut short, remains one of Chestnut’s most memorable performances.
Lance and Mia / The Best Man and The Best Man Holiday
No list of Morris Chestnut romances is complete without Lance Sullivan and Mia Morgan (Monica Calhoun) from “The Best Man” franchise. Lance, a star football player, and Mia, his sweet and devoted fiancée, were the heart of the friend group—until secrets threatened to tear them apart. Their love, tested by betrayal, was one of resilience and faith, culminating in a deeply emotional arc in “The Best Man Holiday” that had everyone reaching for tissues.
