In 2017, Richard Claxton “Dick” Gregory died in the District at the age of 84 with the respect and grassroots appeal bestowed to few, if any, other Black comedians of his time.

The majority of that respect stemmed from Gregory’s penchant for walking among everyday District residents, telling the truth, and advancing civil and human rights causes. He often did this, and more, while cracking a joke or vehemently admonishing public figures and institutions for their heinous acts against marginalized people.

With the limited edition re-release of “Wake Up and Stay Woke,” during this Black History Month, friends, family, comrades, fans and all those in between can continue honoring Gregory’s life and legacy.

This book, originally written by Dr. E. Faye Williams, Esq. in 2021, shares aspects of Gregory’s life unrelated to his comedy and activism. It counts among the several projects done in memory of Gregory since he succumbed to heart failure.

“He was so much more than his comedy, and so much more than his fiery speeches,” Williams wrote on the website for The Dick Gregory Society, an organization she founded in remembrance of the late comedian-activist.

“He has always been about social activism that made a positive difference in the lives of so many who often could or would not speak for themselves,” Williams’ statement continued. “Yes, a big part of his life was about comedy, but it was about so much more, and in this book, I have tried to let you know about who he really was.”

Williams counted among some of Gregory’s closest confidantes. Along with The Dick Gregory Society, she also launched a radio show of the same name on WPFW FM 89.3. She also collaborated with Dr. Christian Gregory, Gregory’s son, on “The Essential Dick Gregory,” a collection of works from the late Gregory.

Gregory was 𝐛𝐨𝐫𝐧 in St. Louis, Missouri in 1932. He went on to author more than a dozen books, including “N*gger: An Autobiography” in 1964 and “Callus on My Soul: A Memoir” in 2000.

Those achievements, and more, came in the midst of a comedy career he started exploring while serving in the U.S. military. That career took off in the 1960s when Hugh Hefner hired Gregory to work at the Playboy Club in Chicago.

As he advanced as a comedian, Gregory courted controversy because of his commentary on race relations and mockery of the political establishment. He supported the fight for civil rights and stood on the frontlines against the Vietnam War and racial injustice, often getting arrested and participating in hunger strikes.

In 1965, Gregory became a vegetarian out of a belief that civil rights and animal rights were aligned. This crusade inspired him to help Black people address health problems stemming from poor diets and substance abuse.

Other causes near and dear to his heart included Native American rights. One quote credited to Gregory asks, “Do you think the Indians celebrate Columbus Day on Indian reservations.”

From the 1970s onward, Gregory appeared on several radio programs. He co-hosted The Power with Kathy Hughes on WOL 1450 AM. He also made guest appearances on “Make it Plain,” the Rev. Mark Thompson’s show on Sirius Channel 146.

While in the District, Gregory remained outspoken about the issues of the day, whether it be the extension of the Equal Rights Amendment in the late 1970s or government complicity in the assassinations of the Rev. Dr. Martin Luther King, Jr. and President John F. Kennedy.

In the years leading up to his death, Gregory could be seen out and about in the District, either perusing the magazine racks at a downtown store, talking to patrons at Sankofa Video Books & Cafe, and even performing a comedy set at Wanda’s on 7th Street in Northwest.

Although he’s no longer here physically, Gregory’s legacy continues to live on in the barrage of video clips that young people growing in their consciousness circulate online. It also lives on through his 𝘤𝘩𝘪𝘭𝘥ren, including Ayanna Gregory, a renowned singer, dramatist, educator and activist.