Kimberly Hebert Gregory, the acclaimed actress best known for her role as Dr. Belinda Brown in HBO’s dark comedy Vice Principals, passed away on October 3, 2025, at the age of 52. The cause of her death has not yet been made public, but the heartbreaking news was confirmed by her ex-husband, actor and singer Chester Gregory, through a moving tribute on Instagram. As tributes from fans and colleagues continue to pour in, many have turned their attention to Chester Gregory, the man who shared an important chapter of Kimberly’s life.
Chester Gregory is a celebrated American actor, singer, and songwriter from Gary, Indiana, born on December 10, 1972. He first rose to prominence for his performance as Jackie Wilson in The Jackie Wilson Story, a role that earned him national recognition and opened doors to Broadway. He made his Broadway debut as Seaweed in Hairspray and later starred in several acclaimed productions including Tarzan, Dreamgirls, Cry-Baby, and Sister Act. His dynamic stage presence and powerful voice made him one of Broadway’s most versatile performers.
Beyond theatre, Chester pursued a successful music career under his artist name “CHΞSS.” He has collaborated with well-known artists such as PJ Morton, Ledisi, and Chance the Rapper, blending soul, R&B, and theatrical influences in his sound. He also runs a personal development and creative mentorship company called Lucid Life, through which he helps aspiring artists and students refine their craft and mindset. In recognition of his contributions to the arts, Chester has received the key to two cities—Gary and East Chicago—and was awarded an honorary doctorate from Columbia College Chicago.
Kimberly Hebert and Chester Gregory met in Chicago’s theatre scene in the late 1990s, where their shared passion for performance and storytelling drew them together. The pair eventually married and welcomed a son, Chester Gregory III. Although they later divorced, the two remained on good terms and continued to co-parent their son with mutual respect and support. Their bond, built on years of friendship and shared artistic values, remained strong even after their separation.
Following Kimberly’s passing, Chester took to Instagram to share a heartfelt tribute that reflected both his grief and gratitude. In his post, he described Kimberly as a force of light, resilience, and artistry, writing, “You taught us lessons in courage, in artistry, in resilience, and in how to keep showing up, even when life demanded more than its share. Thank you, Kimberly, for every chapter we shared. Your story was never defined by the battle, but by the beauty you carried through it.”
His words captured not just the pain of loss but also the deep admiration and love that continued to exist between them. Kimberly Hebert Gregory’s legacy, both as an artist and as a person who inspired those around her, continues to shine through the people who loved her most — including Chester, their son, and the community she touched with her talent and grace.