On Martha’s Vineyard, August has long been more than just another summer holiday month. For generations of Black vacationers, the island, and especially the town of Oak Bluffs, has served as a safe haven, a gathering place, and a cultural hub.
This year, two of the most recognizable figures in American life, Michelle Obama and Supreme Court Justice Ketanji Brown Jackson, brought star power and substance to the annual celebration of Black art, culture, and storytelling.
The pair appeared at the Martha’s Vineyard African American Film Festival (MVAAFF), which was founded in 2002 by Stephanie and Floyd Rance. What began as a small showcase of films by and about African Americans has grown into one of the premier cultural events on the island, drawing filmmakers, artists, writers, and political leaders from across the country.
Michelle Obama’s Family-Style Conversation
At the Performing Arts Center in Oak Bluffs, Michelle Obama joined her brother, Craig Robinson, for a live taping of their podcast IMO. With actress Natasha Rothwell as their guest — affectionately referred to as “cousin” throughout — the conversation flowed like a kitchen table chat.
Together, they tackled themes of mental health, dating, relationships, and the importance of stories that reflect the Black experience.
The crowd responded warmly, laughing as Robinson jokingly offered to set Rothwell up with a suitor, and applauding Rothwell’s cheerful response: “Oh, God is good! I would love to be set up.”
For Obama, the Vineyard remains a deeply personal space.
“This is a special place for us, because, as you all know, this is where we come to enjoy being us,” she told the audience.
Justice Jackson’s Storytelling Journey
Across town at the Island Inn, Justice Ketanji Brown Jackson spoke about her memoir Lovely One, a sweeping narrative that follows her family’s journey from enslavement in the American South to her historic appointment on the Supreme Court.
The book also reflects her early passions in journalism and theater, her marriage to Patrick Jackson, and her progression through nearly every major legal role — clerk, public defender, judge.
With humor, Jackson remarked: “Where I am now, I’m pretty much stuck. So I’m glad I got it all done,” drawing laughter from the audience. Her presence underscored the festival’s theme of storytelling as a form of resilience, identity, and empowerment.
The MVAAFF has grown into a cultural anchor on Martha’s Vineyard, complemented by other major events like the Comedy Fest and Black Book Festival. This year’s film slate featured Spike Lee’s “Highest 2 Lowest” starring Denzel Washington, and HBO Max’s “Seen & Heard 2” on Black representation in TV, moderated by Issa Rae.
In screenings, panels, and casual moments alike, the festival retained a family reunion feel, one where laughter, vulnerability, and cultural pride intersect. Tracee Ellis Ross delighted audiences with her travel documentary, while Ralph Lauren debuted a film on Oak Bluffs’ unique history in collaboration with Spelman and Morehouse Colleges.
More Than a Festival
For longtime attendees, the festival has become not just entertainment but also a form of cultural preservation. Rev. Al Sharpton, Congresswoman Ayanna Pressley, and Representative Jasmine Crockett joined a fireside chat urging Black communities to remain engaged in politics, echoing the civil rights tradition where the arts funded activism.
As Ralph Lauren creative director James Jeter reflected after one screening, “What we discovered were these traditions that happened on this island. It really is one of a kind.”
This year, the traditions of Black storytelling were kept alive — and enlivened — by the presence of Michelle Obama and Justice Ketanji Brown Jackson, two figures who embody the power of narrative, resilience, and history in shaping both culture and nation.
