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You Had Me At Hello: The Love Story of Lillian and Dick Gregory

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The late Dick Gregory’s wife, Lillian, was a cornerstone of his career and activism and an ardent activist in her own right. (Public Domain)

The Birmingham Times 

Comedian and activist Dick Gregory was known by many not just for his comedy career spanning four decades but also for his work in the civil rights movement of the 1960s. Dick Gregory marched alongside Dr. Martin Luther King Jr., Angela Davis, Muhammad Ali, Maya Angelou, Rosa Parks and many others. He was the featured speaker at rallies and protests worldwide, using humor to expose injustice.

Many are unaware, however, that Gregory’s wife, Lillian, was a cornerstone of his career and activism and an ardent activist in her own right. When he marched, she often did too. When he was arrested, she was often sent to jail too. And sometimes, when money was short, and Dick had to turn down a protest to accept a paying gig, he would ask her to go instead, and she did — sometimes with their children by her side.

Born Richard Claxton Gregory on October 12, 1932, in St. Louis, Missouri, Dick Gregory would prove to be an exceptional athlete. Showing off his running skills at Summer High School earned him a track scholarship at Southern Illinois University Carbondale, where he set records as a half-mile and mile runner.

Gregory’s college education was interrupted when he was drafted into the United States Army. But it was in the army that he first performed as a stand-up comedian, entering and winning several U.S. Army talent shows. After his military service ended, Gregory worked at the United States Post Office by day, and by night, performed as a comedian in several small Black nightclubs.

Lillian Estelle Smith was born in Willard, Ohio, the youngest of 14 children — seven girls and seven boys. After high school, she worked for two years to save money to go to her choice school, Ohio State University. But she quit after the first day and left for Chicago, where she found a job she loved at the University of Chicago.

One night, while at the nightclub The Excalibur with her sister, Lillian met a “cute” comedian named Dick Gregory, who would become her husband and the father of her 11 children. Dick and Lillian married in 1959, and Lillian’s nickname for Dick became “my damn fine cat.”

In the 1960s, Dick Gregory began to receive national acclaim as a comedian and also became increasingly involved in the Civil Rights Movement. Together, Dick and Lillian Gregory organized voter registration drives, marched for freedom, and faced jail. Lillian even spent nearly two weeks in jail while pregnant with twins in 1963.

When she wasn’t out protesting, she was busy taking care of their home and their 10 children. (They lost one child, Richard, three months after he was born.) Also, Lillian managed many inquiries for her husband, which led him to famously tell people to “Call Lil.”

Dick and Lillian Gregory. (Paula Cenac, StoryCorps)

Dick’s vision went beyond civil rights in the U.S. He fought against apartheid in South Africa and against war, sexism, animal cruelty, and public health neglect worldwide.

Meanwhile, Lillian Gregory’s resolve made their legacy a beacon of hope and kept their family nurtured and cared for, as the Plymouth Independent stated in a 2025 article.

Throughout the 1980s, Gregory was also known for his strong voice in the health food industry. Seen as a nutrition guru, Gregory advocated plant-based diets of raw fruits and vegetables.

In 2004, Gregory was listed as number eighty-one on Comedy Central’s list of the 100 Greatest Stand-Up Comedians of All Time. He also has his own star on the St. Louis Walk of Fame.

Dick Gregory died in August 2017. Lillian developed Alzheimer’s disease shortly after Dick’s death but in 2018, Lillian was honored at the Montgomery College Cultural Center in Maryland.

“I look back on my life and think, this little Black girl from this little town of Willard, Ohio, coming to Chicago by happenstance and things just happened,” Gregory said in an interview with The Washington Informer at the time of the tribute. “I can’t tell you why. I can only say it was God’s plan and I had a wonderful life.”

Published in the program for the event were these words from Dick about Lillian: “And to the folks out there whose whole lives were filled with hatred and bigotry, y’all needed a Lillian. The world would be better off if they had a Lillian. You don’t need but 1.”

At the 2018 event, inspirational author, coach and television personality Iyanla Vanzant served as the keynote speaker and marveled at the decades-long Gregory marriage.

“What kind of woman stays married to one man for 58 years?” she asked. “What kind of woman stays in the background and does the work, is the backbone and doesn’t need the glory? What kind of woman? The kind of woman I aspire to be.”