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Insecure’s Issa Rae: ‘There are still so many stipulations about what Black stories I am allowed to tell’

Issa Rae’s new collaboration with Madewell showcases Black talent across the board.

Insecure’s Issa Rae: ‘There are still so many stipulations about what Black stories I am allowed to tell’
[Photo: Madewell]
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You probably know Issa Rae from her acclaimed HBO show, Insecure, which spun out of her popular YouTube show, Awkward Black Girl. But behind the scenes, Rae is building an empire as a best-selling author, a producer and director, an entrepreneur, and the owner of a record label as well as a talent management agency focused on underrepresented writers.

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As Rae has navigated these industries, she’s seen firsthand how hard it can be for Black creatives to tell their stories. That’s why she’s committed to using her platform to champion emerging Black artists across many mediums, from writers to songwriters to photographers.

We see this at work in Rae’s collaboration with Madewell for the fashion brand’s spring campaign, which launches today. She brought the ad to life using her production company, Color Creative, and her music label, Raedio. And throughout the campaign, which will run for six weeks, she draws attention to many young Black women, including novelist Yaa Gyasi, art curator Autumn Breon, and poet Tonya Ingram, whose work will be referenced throughout the campaign.

Issa Rae [Photo: Madewell]
I spoke with Rae about the hurdles that Black creatives face and why it’s important for brands to hire Black talent throughout their entire operation, not just as the face of the project.

Fast Company: You’re part of so many exciting endeavors these days. Do you still struggle to bring some projects to life?

Issa Rae: I have found that there are certain types of stories from Black creators that just don’t get greenlit because there is still an impression that they won’t translate [to white audiences] or they won’t sell. It is frustrating that studio executives are gatekeepers, deciding what Black stories are worth telling. It’s insulting.

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There’s so much more to tell beyond the dramatic or historical stories about the Black struggle. There are things we want to see beyond that. We still don’t get much of the “slice of life” content or romantic comedies with two dope Black leads. There are still so many stipulations about what Black stories I am allowed to tell.

FC: So much of your work has been about giving the viewer an authentic look into the everyday lives of Black young people, including their relationships and sexuality. Why do you think this is so important?

IR: I am an avid watcher of movies and television shows and whenever I see, like, Black people having sex on screen, it is often either traumatic or hyper-, hypersexualized. With Insecure, I wanted to show Black people making love and having sex in a way that was sensual or sexy. And also awkward, because that’s the realistic and also fantastic nature of sex.

FC: Many people know you from Insecure, but you’re actually involved in many other projects. Can you talk a little bit about that?

IR: I got my start creating the web series Awkward Black Girl. And when you create on the internet, you have to be a multihyphenate. You’re creating content, but your goal is to ultimately sell that content. So you need to build and lead a team that will help you market it.

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I’m still doing that on a bigger scale. I’m creating content for television and a podcast. I produce films—some of my own, and some of my collaborators’. And then there are side ventures, whether it’s a hair company or a coffee company. I also have a music label, where I work with other artists, and a management company. So I’m now indirectly helping to manage the careers of other creatives.

FC: With this Madewell project, you’re also showcasing Black creatives. What are some strategies brands can use to support Black talent?

IR: I feel like I have a door open to me to create certain projects and I have a responsibility to bring other people through this door. And this applies to everyone involved with a creative project.

There have been projects I have worked on—from ad campaigns to films—where literally 99% of the people on the set are white guys. It’s like, “Y’all didn’t even try.” Even when you have a Black person as a lead, you need to bring on board other Black creatives as part of the project. It has to be part of your mandate.

Madewell was an example of a company that didn’t just work with me, but also created with me. I was able to have a say in who was on the team, including bringing on a director that I am a fan of. They brought on a young Black VP whose work I had never seen before. Just being able to curate who I wanted to collaborate with was so important.

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[Photo: Madewell]
FC: How does having Black creators throughout the project change the outcome?

IR: It can have a tremendous impact. Sometimes it is as small as bringing on people who know how to light Black talent or do their hair and makeup. I have seen the difference in photo shoots when the photographer is Black. I have been poorly lit, which has made me look ashy on camera. So now I have to ask, has this photographer shot Black or dark-skinned people? Can I see those samples? That’s not me being demanding; they don’t have to be Black or female, I just need to know that they can shoot me.

This also reveals the double standard in the industry. For instance, Black hairstylists can work on Black hair, but they are also expected to be able to work on all types of hair textures. But many white hairstylists don’t know how to work with Black hair. In this industry, we have to understand every facet of the culture just to be able to play within this space. But this is not expected of everyone.

FC: You got your start by creating Awkward Black Girl online, which then got picked up and transformed into Insecure. Do you think these new platforms are helpful to young Black creatives who have historically had a harder time breaking into Hollywood?

IR: Social media is amazing because it gives Black writers and creators a platform. But I think there are some challenges now. When the content is free and can be easily copied—especially with TikTok, where the norm is to put your own spin on something someone else created—it can sometimes be harmful to the originators of popular content.

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So it helps when there are people who say, “No, we’re going to find out who made this and give them their flowers.” There’s something beautiful in that. But it is hard to get noticed because there are just so many opportunities to create that people’s attention spans just move on to the next thing so fast.

Creating on your own is great. But for me, everything came down to who I was collaborating with. I wanted to work with people who thought differently and who were smarter than I was. I continue to work with these people and expand my range of collaborations. I’m not someone who needs people to think I’ve done all the work on my own. I would encourage people who are coming up to collaborate with people who are around you, those who are hungry and passionate to make an impact on the world.

About the author

Elizabeth Segran, Ph.D., is a senior staff writer at Fast Company. She lives in Cambridge, Massachusetts

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