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Michelle Obama and Ketanji Brown Jackson Draw Crowds on Martha’s Vineyard

In Oak Bluffs, Mass., film premieres, book fairs and star-studded soirees attracted fans who came for the art and stayed for the community.

Craig Robinson and Michelle Obama recorded their podcast “IMO” at the 23rd Annual Martha’s Vineyard African American Film Festival on Saturday. Credit...Gabriela Herman for The New York Times

Craig Robinson and Michelle Obama recorded their podcast “IMO” at the 23rd Annual Martha’s Vineyard African American Film Festival on Saturday. Credit...Gabriela Herman for The New York Times

Black vacationers on Martha’s Vineyard often describe visiting the island in August as a kind of family reunion. If your family happens to include Michelle Obama, that is.

“This is a special place for us, because, as you all know, this is where we come to enjoy being us,” Ms. Obama said Saturday afternoon at the Martha’s Vineyard African American Film Festival, where she joined her older brother, Craig Robinson, for a live recording of their podcast, “IMO,” which she likened to a kitchen table.

The brother-sister duo were speaking with the actress Natasha Rothwell, whom they repeatedly referred to as “cousin,” inside the Martha’s Vineyard Performing Arts Center in Oak Bluffs, Mass., where many of the film festival’s events were held.

 

Natasha Rothwell sits in a chair holding a microphone on stage.
Natasha Rothwell spoke with Ms. Obama and Mr. Robinson for their podcast. Credit...Gabriela Herman for The New York Times

Together, they discussed mental health, dating, relationships and the importance of telling stories that reflect the Black experience. In a display of almost familial warmth, Mr. Robinson even offered to set Ms. Rothwell up with a potential suitor, which drew applause and laughter from the audience.

“Oh, God is good!” Ms. Rothwell exclaimed. “I would love to be set up.”

The quaint island off the coast of Massachusetts has been a central destination for Black vacationers for more than a century, specifically the town of Oak Bluffs, which became a popular summer destination by welcoming Black Americans during segregation when most beaches and resorts turned them away.

 

Crowds assembled outside the Martha’s Vineyard Performing Arts Center.Credit...Gabriela Herman for The New York Times
Crowds assembled outside the Martha’s Vineyard Performing Arts Center.Credit...Gabriela Herman for The New York Times

But with the introduction of the film festival by Stephanie and Floyd Rance in 2002, the Martha’s Vineyard Comedy Fest by Steve Capers in 2010, and the Black Book Festival by Traci Wilkes Smith in 2024, plus a busy calendar of additional events, Black politicians, filmmakers, artists, writers, celebrities and fans now converge on the island during the first two weeks of August.

Earlier on Saturday, across town, at the Island Inn, the Supreme Court Justice Ketanji Brown Jackson discussed her 2024 memoir, “Lovely One,” with Ms. Wilkes Smith.

Justice Jackson’s memoir charts her family’s journey from enslavement in the South to her grandparents’ move to Florida; her own childhood there; early stints in journalism and theater; her marriage to her college boyfriend, Patrick Jackson; and her law career, which led her to the Supreme Court.

 

Traci Wilkes Smith, the founder of the Black Book Festival, presented Justice Ketanji Brown Jackson with the festival's first “Distinguished Author Award.”Credit...Gabriela Herman for The New York Times

Justice Jackson told the audience — with a chuckle — that she was grateful that she held roles as a law clerk, public defender and judge because, “Where I am now, I’m pretty much stuck. So I’m glad I got it all done.”

The gatherings this year began even before touchdown at the island’s only airport. Two women dressed in the colors of Alpha Kappa Alpha, a historically Black sorority, spotted each other as they were boarding the plane and struck up a conversation. Within minutes, they realized they had attended the same university and had mutual friends.

 

 

Clockwise from top left, Michael Harvey; Candace Johnson; Imole Ladipo; Carmen Morgan.Credit...Gabriela Herman for The New York Times

Buzz at the film festival, which ran Aug. 1-9, centered on films like “Highest 2 Lowest,” directed by Spike Lee and starring Denzel Washington, as well as “Seen & Heard 2” a documentary from HBO Max, highlighting the evolution of Black representation in TV, that was followed by a discussion moderated by Issa Rae.

At many events, there was a sense of lightness, conviviality and letting down your hair — a sentiment echoed by many of the festivalgoers and speakers. They spoke of how, on the island, Black people could trip and fall, laugh at themselves, and feel as though they were surrounded by family.

That was true at a screening of “Solo Traveling With Tracee Ellis Ross,” where the actress laughed loudly at her own antics onscreen, at one point covering her eyes during a scene in which her luggage was searched in Paris and security found, as she put it, “a lovely little bag that has things that are usually in your bedside table.”

 

Lindsay Peoples, the editor in chief of The Cut, and Tracee Ellis Ross at a screening of Ms. Ross’s travel show. Credit...Gabriela Herman for The New York Times
Lindsay Peoples, the editor in chief of The Cut, and Tracee Ellis Ross at a screening of Ms. Ross’s travel show. Credit...Gabriela Herman for The New York Times

 

Inside the auditorium at the Martha’s Vineyard Performing Arts Center, the audience danced in their seats.Credit...Gabriela Herman for The New York Times
Inside the auditorium at the Martha’s Vineyard Performing Arts Center, the audience danced in their seats.Credit...Gabriela Herman for The New York Times

An audience filled with H.B.C.U. alumni (and celebrities such as Dave Chappelle and Gayle King) also packed the screening of a documentary created by Ralph Lauren, “A Portrait of the American Dream: Oak Bluffs,” to accompany its Polo for Oak Bluffs collection, which launched last month in collaboration with Spelman and Morehouse Colleges.


Gayle King at the festival.Credit...Gabriela Herman for The New York Times


Valerie Jarrett, a director on Ralph Lauren’s board and chief executive of the Obama Foundation, joined James Jeter, the creative director, design and brand director at men’s Polo Ralph Lauren; Cole Brown, the documentary’s writer-director; and David Wall Rice, a professor at Morehouse College, after the screening to discuss what makes Oak Bluffs special to the Black community.

“It really is one of a kind,” Mr. Jeter said, explaining how the creative team was welcomed into people’s homes as they shared family photo albums. “What we discovered were these traditions that happened on this island.”

 

Panelists Carla Thompson Payton, Valerie Jarrett, James Jeter, Cole Brown and David Wall Rice discussed the significance of Oak Bluffs on Friday.Credit...Gabriela Herman for The New York Times
Panelists Carla Thompson Payton, Valerie Jarrett, James Jeter, Cole Brown and David Wall Rice discussed the significance of Oak Bluffs on Friday.Credit...Gabriela Herman for The New York Times

For longtime residents like Melvin Thornhill, 88, and Vida Mitchell, 73, the August festivities are an excuse to get out, try new things and see big names. One of this year’s big tickets was a fireside chat between Rev. Al Sharpton and the U.S. Representatives Jasmine Crockett and Ayanna Pressley.

“I read about Ms. Crockett, and she’s a real go-getter,” Ms. Mitchell said.

“I’m from New York, and we know Al Sharpton, so I came to see him again,” Mr. Thornhill added.

The Rev. Sharpton and Ms. Pressley received a warm welcome, but it was Ms. Crockett, who represents Texas’s 30th congressional district, who brought the crowd to its feet.

The session, billed as a conversation about finding joy in bleak times, soon turned toward President Trump, whom the panelists critiqued sharply.

 

U.S. Representatives Jasmine Crockett and Ayanna Pressley, Reverend Al Sharpton and Leslie Herod spoke at the film festival on Thursday.Credit...Arturo Holmes/Getty Images
U.S. Representatives Jasmine Crockett and Ayanna Pressley, Reverend Al Sharpton and Leslie Herod spoke at the film festival on Thursday. Credit...Arturo Holmes/Getty Images

At one point, they returned to the festival’s theme, urging attendees to get involved in local politics.

“The arts were the ones that financed the movement,” the Rev. Sharpton reminded the crowd. “Harry Belafonte and Aretha Franklin went on tour so that Dr. King could make payroll.”

Yola Mzizi is a reporter for the Styles section and a member of the 2025-2026 Times Fellowship class, a program for journalists early in their careers.

Author: Yola Mzizi Reporting from Oak Bluffs, Mass.

Source: N.Y Times

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