In the summer of 2020, several unrelenting months into the COVID pandemic, comedian Dave Chappelle decided he had to do something to bring his community back to life. Like the rest of the world, Chappelle was sequestered at home with his family, so he decided to use his resources to make a change. After renting out a cornfield down the street from his home in Yellow Springs, Ohio, Chappelle began hosting socially distanced concerts with his friends, musicians and fellow comedians. He filmed the entire process for the independent documentary, “Dave Chappelle: Live In Real Life.”
The film, directed by Steven Bognar and Julia Reichert, premiered at the Tribeca Film Festival in 2021, under its original title, “Dave Chappelle: This Time, This Place.” However, it failed to gain distribution after the backlash to his 2021 stand-up special, “The Closer,” in which he told a series of transphobic jokes. Now, four years later, the retitled documentary screened at the 23rd annual Martha’s Vineyard African American Film Festival (MVAAFF) on Friday night. After the credits rolled, Chappelle took the stage to address the audience and even spoke candidly about those poorly received jokes, “I’ve gone on to get snubbed by the Grammys and the Emmys because someone thought it was a good idea to tell trans jokes,” he said.
“Dave Chappelle Live In Real Life” seems to be a sign that the Grammy-award-winning comedian is focusing on something new. The documentary is heartfelt and full of Chapelle’s signature humor, showcasing familiar faces — everyone from Kevin Hart, David Letterman, Jon Hamm, The Roots and Chris Rock — who stopped by on the weekends to riff, chat and dance with audiences during those summer shows.
“It took a lot of courage for all of those comedians to come out there because COVID was so new. Everyone was still so isolated, and it was real fear,” Chappelle said during the post-screening talkback in which he took questions from the audience (a sold-out crowd that included fellow comedian David Letterman and CBS News’ Gayle King). “And the other thing is, no one had worked in a hundred nights. Everyone stunk when they got there, but it didn’t matter. It was so much fun to be together again. It was just like when we all started in the comedy club, we realized how much we loved being around each other.”
Regina Lasko, Elaine Chappelle, Dave Chappelle, David Letterman, and Gayle King attend the screening of “Dave Chappelle: Live In Real Life” during the 2025 Martha’s Vineyard African American Film Festival.
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The film screened at MVAAFF as part of Chappelle’s efforts to raise funds for his alma mater, the Duke Ellington School of the Arts in Washington, D.C. Proceeds from the event’s ticket sales went to the high school, which the comedian has credited for changing his life. “Ellington gave me a sense of community,” he said. “It was a predominantly Black school when I went there, and that was important because everything in the news was so negative.”
“Dave Chappelle: Live In Real Life” chronicles how the comedy show expanded into a summer series with more than 50 shows produced to date, a phenomenon that thrilled some Yellow Springs residents and enraged others. It also showcases the lengths that Chappelle and his crew went to ensure that everyone in the audience, as well as the performers and crew, remained safe and healthy.
“During the summer of 2020, it was about to be a mass exodus from the town,” he said, reflecting on Yellow Springs’ economic state. “People wanted to sell their shops and their businesses. The reason I knew this is because everyone would see me on television and assume I had all this money… because I do. So they were coming, trying to sell me all this shit. And I realized that, oh man, everyone’s leaving. This is going to be a big deal. So quietly, I bought a lot of real estate in the town. This is not something that I wanted to do. It was something that was necessary in the moment. And they were pleased about it because I didn’t charge anybody rent for two years.”
Chappelle shared that not only did the summer shows safely bring people together who were struggling in isolation, but they also contributed $9 million to the town’s economy. For him, the mission was simple. “If you want things to change, you have to change shit,” he said.
Dave Chappelle in “Dave Chappelle: Live In Real Life.”
Image courtesy of MVAAFF.