Dave Chappelle Honors David Letterman at Tribeca Screening of Unreleased Documentary

When it comes to Dave Chappelle, nothing happens quietly, and that includes a documentary screening. Recently, at the Martha’s Vineyard African American Film Festival, comedy legend Chappelle gave the audience a rare peek into his unreleased documentary, Dave Chappelle: Live in Real Life. The doc dives into his pandemic-era cornfield comedy shows, which, yes, sound peculiar—but also kind of genius. And it being a Chappelle event, there was naturally a Q&A session filled with Chappelle’s signature wit, surprises, and a bit of controversy.

What’s the Deal with This Documentary?

For those not keeping up, Live in Real Life is Chappelle’s unreleased gem. The film captures the magical (and chaotic) cornfield comedy shows he orchestrated in Yellow Springs, Ohio, during the peak of COVID-19. We’re talking socially-distanced audience setups, mandatory masks, and a whole lot of humor when the world was craving some.

Originally called This Time This Place, the doc premiered at Radio City Music Hall during the 2021 Tribeca Festival. But, as with most things associated with Chappelle, it faced its fair share of controversy. His Netflix special The Closer sparked backlash for its trans jokes—which reportedly impacted the documentary’s distribution. Classic Chappelle move though? He turned that roadblock into yet another tour, screening the doc alongside live comedy shows because, well, “Why not?”

The Martha’s Vineyard Affair

The 23rd annual Martha’s Vineyard African American Film Festival served as the latest setting for the movie. Hosted at the Performing Arts Center, the screening was as much about laughs as it was about heart. Who else but Chappelle could tell a story blending comedy, the pandemic, the murder of George Floyd, and the Black Lives Matter movement into one narrative? It even featured his cornfield neighbors who helped Chappelle test the waters for a prototype of socially-distant live shows. Oh, and no texting during this one—even press attendees had their phones zip-locked shut. Old-school rules? Maybe, but it added to the exclusive vibe.

Dave Chappelle Being Peak Dave Chappelle Onstage

After the screening, Chappelle hit the stage in sneakers (naturally) and a suit for an unscripted talkback. Confessing he didn’t realize a Q&A was planned, he joked, “I didn’t read the brochure, I just showed up.” Classic. He credited the cornfield shows as a way to make sure “his voice was out there.”

Shouting out David Letterman, who was in the audience, Chappelle called him the gold standard for comedy. Letterman returned the love by joking that if young comedians “aren’t as good as Dave Chappelle, there’s no need to move to LA.” Solid advice.

The comedian didn’t dodge the elephant in the room. On the claims that his comedy stirred controversy, he quipped, “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.” And yes, this is the same Chappelle who’s won those awards since. Talk about irony.

Chappelle’s Community Roots

Among all the quips and jokes, the heartfelt moments stood out too. Chappelle discussed the role his alma mater, the Duke Ellington School of the Arts, played in his life. “Ellington gave me a sense of community during a time when the media painted a negative picture of the Black community,” he explained. It was this sense of belonging that inspired him not just to create the comedy shows but also to fundraise for his D.C. school’s benefit.

Whether you’re a die-hard Chappelle fan or someone still side-eyeing him over past controversies, it’s impossible to deny the guy’s impact on comedy (and, apparently, his cornfield). While Dave Chappelle: Live in Real Life isn’t widely available yet, it’s undoubtedly a work of art worth waiting for. Will it see mainstream release, or will Dave keep it as his personal treasure? Knowing him, your guess is as good as ours.

For now, we can only hope the King of Stand-Up keeps finding ways to stay “live in real life.” After all, the world could use a good laugh (or 50).