Issa Rae: “We’re Really Out Here Winning”

Issa Rae: “We’re Really Out Here Winning”,Issa Rae, the prolific writer, actress and producer, on embracing ensembles, championing others and carving out time for herself.

Issa Rae: “We’re Really Out Here Winning”

Asked who in Hollywood she’d want to trade places with for a day, Issa Rae responded, “Oprah.”Danielle Levitt/Guardian/Eyevine/Redux

After her longtime gig Insecure came to an end last year, Issa Rae didn’t miss a beat in launching the next phase of her career. With a five-year overall deal with WarnerMedia, Rae, via her Hoorae production company, created and executive produced HBO Max comedy Rap Sh!t and is developing a revival of docuseries Project Greenlight. Rae landed her third Emmy nom for best actress in a comedy this year, and her onscreen career continues to flourish, with roles in B.J. Novak’s Vengeance, an upcoming appearance in Greta Gerwig’s Barbie and a voice performance as Spider-Woman in Spider-Man: Across the Spider-Verse.

I think it means a level playing field and opportunity for all. “Representation” has been a buzzword that’s been used several, several times, and the industry has thought to give people opportunities, but not necessarily put that into action. It’s been a talking point with nothing to be done until, I felt like, 2020 lit a fire under people’s asses; it’s just been more telling to see who’s continuing to talk that talk and who’s walking it back.

Do you feel there’s a sisterhood among powerful women? Who do you reach out to for advice?

There are women that I admire, that I feel like I could call and should call — I just had that revelation last month. I was like, “There are so many women I know who are going through exactly what I’m going through, why am I not picking up the phone to call them?” I remember talking to America Ferrera once, and we had the best conversation and she was like, “You need to hit up Reese [Witherspoon] or Mindy [Kaling]” and I was like, “I should,” and then still didn’t because I always feel like I’m bothering people. But whenever I do get a chance to catch up with them, I feel more empowered. I feel like, “OK, I’m not crazy, I’m not in this alone.” Maybe in 2023, I’ll be more intentional about reaching out.

How do you find time to mentor others?

Even the times when I’m perusing people’s videos or getting recommendations from others, you just become an actual fan and you want people to have more visibility. It doesn’t feel like mentorship, it feels like, “Oh man, I want everybody to know about you.”

We’re at about a year since Insecure ended. Did you take any time to decompress after that final season, or did you jump right into other things?

I took time to decompress. Literally right after the episode ended, I just jumped on a plane and took all of January off. This year, despite having Rap Sh!t out, I wasn’t in it, so it’s probably been the most relaxing — relaxing for my standards — year I’ve had in, like, 10 years.

How was that transition from starring in your own show to taking a more behind-the-scenes role as creator and writer?

It’s the best, just sitting on my ass and watching people be great while eating all day. I was like, “Oh, OK, writers have the best job ever.” (Laughs.) But there was the stress of making sure that the follow-up to Insecure would be something that people liked and that they didn’t compare too hard to Insecure. So there was pressure, but being behind the scenes is so much more fun, and it’s really rewarding.

Have you felt your creative interests change since you’ve wrapped and had time to breathe?

Absolutely. Now I’ve kind of figured out what I want my next three shows to be and I’ve been working on those. Some I’m in, some I’m not, but it really just lit a fire under me to keep creating. Being on Insecure, so much of my time was that, and I didn’t get to even write Rap Sh!t until the pandemic happened and we had that kind of forced break. So I realized that maybe I’m not that great at multitasking and I need to carve out time to be able to continue to create, because that’s what makes me the happiest. That’s what makes me the most excited. And Rap Sh!t demonstrated that for me from its inception to finally completing it.

Months after finishing Insecure, Issa Rae delivered since renewed comedy Rap Sh!t to HBO Max.Courtesy of HBO Max

How has it been to see your Insecure cast follow up with such big projects: Jay Ellis in Top Gun: Maverick, Yvonne Orji landing an HBO comedy special, and Natasha Rothwell starring in and co-showrunning Hulu’s How to Die Alone?

It really does feel like “Oh, we’re really out here winning.” We were just texting each other. It’s so hard to connect, Jay’s shooting in Oakland, Yvonne’s traveling, Natasha has her show going — I have to find the text to get her quote correct. She said, “Issa, you never told us running a show was like putting your face in a blender and loving it.” (Laughs.) Leading her own show, her starring vehicle, like that is the dopest thing in the world to me. I’m just really proud to see what everybody else is gravitating toward and to see them killing it.

What are you looking for in acting roles now?

I kind of love ensemble work, like Vengeance or Barbie. I’m trying to look to play a small piece in a larger story; I love that right now.

How did that role in Barbie come about?

I had a meeting with Greta. I’d met her once before, at the BAFTAs, and really, really loved her. We got to express our love for each other and for Lady Bird and Insecure. That was years ago, and then at this meeting, she was like, “I don’t know if you remember me,” and I was like, “Girl, if you don’t shut up.” She was explaining the Barbie script to me. She was like, “I just need to explain what it is.” And I’ll be 100 percent honest, when she was talking, like, it was entertaining, but I didn’t get it. I was like, “I don’t know what the fuck she was talking about, but whatever it is, I’m excited she’s behind it.” And then reading it was, like, “Oh my God, I love her even more.” And then actually shooting it, it was incredible, one of my favorite experiences.

With so many changes in the industry right now, how do you feel it’s affecting creatives?

When isn’t there [change]? But this in particular feels like nobody knows what’s happening. Everybody’s just at the mercy of all these consolidations and mergers. So many writers are getting the short end of the stick. I know it’s just made me more dedicated to ownership and to making sure that we stay committed to what we’re doing, in terms of being able to open the door for others and keep that door open. That’s the only thing that feels different from decades past, when [there was] this fear of losing persity and going back to the status quo. There are people with good intentions who are less fearful about speaking up [now], and the democratization of outside voices demanding, “This is what we want to see and we’re going to hold your feet to the fire until you do something about it.”

What’s still on your career bucket list?

I still want my studio in South L.A. — that’s at the top of the list.

Interview edited for length and clarity.

This story first appeared in the Dec. 7 issue of The Hollywood Reporter magazine. Click here to subscribe.