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Jeneé Osterheldt

Issa Rae and the art of making space

Since the finale of “Insecure,” questions have swarmed about her legacy. Issa Rae is just getting started.

Issa Rae attended HOORAE x Kennedy Center Takeover at The Kennedy Center in Washington, D.C., on March 25.Tasos Katopodis/Getty Images for HOORAE

WASHINGTON — At the Kennedy Center, in the nation’s capital, Issa Rae celebrated Black folk as a fine art.

Over 6,000 people in all shades of black, brown, and gold poured through the halls and theaters of The John F. Kennedy Center for the Performing Arts last weekend, where the scent of sandalwood and shea butter wafted gently in the air.

With faces masked and vaccination wristbands, the hugs and laughs were plentiful. It was more than one thing. It was a weekend of everything: A concert by Mereba, short films, The Read live comedy album by Kid Fury and Crissle, a conversation between Issa Rae and Keke Palmer, plus panels and parties.


She could have done this in Los Angeles, where she does so many events, back home where her companies are headquartered. But Simone Eccleston, the inaugural director of hip-hop culture and contemporary music at the center, invited Rae and the world she is building.

“I have to say that the thing that’s most special about being here is that a Black person, a Black female who works here, reached out to us to bring us here. I feel like that is necessary, like that in some ways the only way that we get to be in these spaces is because someone is looking out,” Rae said in a roundtable interview.

For a lot of us, 2022 has been about re-emerging into life outside. Rae is like us that way. Except she’s doing it at The Kennedy Center.

“This year is to kind of just reintroduce what we do to the industry,” she said. “And to be able to do that in a place that celebrates culture and have them celebrate Black Culture and uplift it, this means the world to me and us.”


A living memorial to John F. Kennedy, our most arts-driven president, the center is celebrating its 50th anniversary season. As they put their programming together, they kept Kennedy in mind.

“I see little of more importance to the future of our country and our civilization than full recognition of the place of the artist,” he said at Amherst College in 1963.

An artist’s place is everywhere. Too often, we’ve allowed institutions to dictate to us what constitutes high art, assigning elite values to a very exclusive club of creatives that has all too often left out Black people and folk of color.

So we made space. We have our Basquiat, Alvin Ailey, Ava DuVernay, and Kendrick Lamar. We have our Donald Glover, Queen Latifah, and Questlove. Our cup flows with creative genius.

And Issa Rae helps fill it. She may have started with “Awkward Black Girl” on YouTube and “Insecure” on HBO, but Rae is making more than art. She is creating space. The $40 million deal she signed with HBO last year is for both films and television. With every opportunity she gets, she brings rising voices to the table.

Keke Palmer and Issa Rae spoke onstage at the Kennedy Center on March 27, 2022. Tasos Katopodis/Getty Images for HOORAE

Her media company, HOORAE, houses film, TV, and digital ventures. It includes ColorCreative Management, a company specifically for women and creators of color. Plus her label, Raedio, is more than a music label. They do podcasts, concerts, and get music placed in campaigns, TV, and more.

“As a company, one of the things that’s an ethos is not just the scaling of the business but scaling our impact,” said Morgan Davis, director of brand partnerships, events, artists relations at Raedio/HOORAE.


The takeover, with tickets intentionally priced between $25-$89 for accessibility, was about bringing the Black community in.

“Reimagining the notions of spaces where Black people attend, where we’re accepted, where we are seen — one of the biggest things is returning equity back to Black people,” she added.

And this is what Eccleston wanted to bring to the Kennedy Center. JFK cared about the freedom and space of an artist. Rae is furthering that vision by reclaiming space that was always ours to have, and making more where we thought we had none.

“As part of the Kennedy Center’s 50th anniversary, one of the core things for us was really looking at the individuals and the organizations that are not only creating work that is of the moment, of the day, but are doing things that will carry us forward,” Eccleston said. “I would say that I think that Issa Rae is one of the most important visionaries of our generation.”

The Kennedy Center has been working its way here. In 2014, the center teamed up with Nas and the National Symphony Orchestra. In 2016, Q-Tip was named the center’s first artistic director of hip-hop culture. In 2017, Eccleston became the inaugural director of hip-hop culture and contemporary music. By 2018, the center announced its Hip Hop Culture Council.

The door just widens and widens. Last weekend, HOORAE screened comedian Kid Fury’s new documentary, “Undertow,” about his battle with depression. Another short, “If These Locs Could Talk,” explored the meaning of locs. As part of The Read’s comedy album, young rapper Flo Milli came to the Kennedy Center stage. Rae and the Kennedy Center are adding to the nuance of who and what can and will be celebrated.


“I think about that moment, Issa Rae’s famous statement, ‘I am rooting for everyone Black,’ ” Eccleston said. “What you saw this weekend was the most divine manifestation of it. What HOORAE is doing is legacy work and helping turn the tide for generations of creatives as it relates to resources and opportunity.”

Mereba performed during HOORAE x Kennedy Center Takeover at The Kennedy Center on March 25, 2022 in Washington, D.C. Tasos Katopodis/Getty Images for HOORAE

For musician Mereba, who opened the weekend with a soulful and jazzy concert, this type of community building is refreshing. Mereba performed as part of “pieces,” a live version of Rae’s Web series bringing the stories behind our favorite artist’s songs.

“I just admire how Issa spreads her light and she is not afraid to also spread other people’s light. It’s so incredible,” the songstress said after her performance. “It’s not exploitive, it’s not just for a quick look. It’s real support, from like a sister, and it’s super inspiring and it’s super empowering and I would love to see more of that.”

At the heart of everything Rae does is community and opportunity.

“We wanted to build something that had an ecosystem, so if you come through one door, you are not stuck in that one room,“ said Benoni Tagoe, Raedio president and Rae’s longtime friend. “Now that her career has grown and she’s in a position to be able to provide opportunities, Issa is reaching back and bringing people up.”


New voices and collaboration, Rae believes, are key to how we grow as a people and as an industry.

“I know what it’s like to not have opportunities and to be seeking them and to feel like no one cares in the mainstream when I know the non-mainstream does,” she said. “To always be able to have my eye on what others are doing that I know I appreciate, that I know, culturally, others would appreciate is important to me.”

She is always looking for talent, opening doors, and sitting in conversations with creatives she admires — be it Keke Palmer or Melina Matsoukas. This is part of how she builds and expands HOORAE.

“I also feed off of working with other hungry people and working with people who are passionate and want to be here because you can get disillusioned working in this industry,” she said.

“To work with people who are finding a new way in and are rich with new ideas only makes me more excited and makes me feel more empowered to make all the difference,” Rae added. “I think that we only get stronger working with and giving opportunities to people outside of the industry. I think that’s how the industry gets better.”

When “Insecure” aired its final episode last year, it was a bittersweet goodbye. That show, from the music to the fashion to the businesses they supported and, obviously, the storylines, was a love letter to us. So many stars who were told they would never beam were able to shine because of it. Closed doors began to open.

JFK believed the artist was the last champion of the individual mind and logic against “an intrusive society and an officious state.”

With Issa Rae — an artist faithful to the culture, driven by her purpose and her creativity — our champ is here.

Jeneé Osterheldt can be reached at jenee.osterheldt@globe.com and on Twitter @sincerelyjenee and on Instagram @abeautifulresistance.