2020: The Year Issa Rae Makes Us Laugh, Cry and Disrupts Hollywood's Status Quo


When I enter the West Hollywood studio space where our February cover shoot is taking place, my attention is immediately drawn to Issa Rae sitting poised with impeccable posture in front of the camera. For someone wearing an extravagant concoction of baby-pink feathers, fuchsia satin, and enormous heart-shaped crystal earrings, she had a rather serious expression on her face. "You wear stuff like that and you wonder why,” she jokingly admits to me later. "For the ’gram, that’s it.”

Rae sinks into the cracked leather sofa beside me, having swapped the fluffy Prabal Gurung ensemble I first saw her in for a more laid-back athleisure look consisting of black leggings, a T-shirt, and sneakers, but she maintains her poised posture. We’re 11 days away from the end of the year, and while everyone in my orbit is recapping the past 365 of their lives in carefully constructed galleries on Instagram, Rae is racing full steam ahead into 2020. She’s just wrapped production for the much-anticipated fourth season of her award-winning HBO series Insecure, out April 12 (mark your calendars), and will be starring in two back-to-back feature films this spring, with more projects already in the pipeline. This past fall, she inked a deal with Atlantic Records to launch her record label, Raedio, and became the co-owner of the black-owned and -operated Hilltop Coffee shop in her hometown of Inglewood. Oh, and did we mention she also owns two production companies? We all like to subtly flex about how busy we are, but Issa’s been busy. "It feels like a lot,” she says anxiously of the coming year, "but I’m just excited for people to see what I’ve been up to.


(Image credit: Taylor Rainbolt; STYLING: Mary Katrantzou dress; Chanel earrings)

She’s particularly excited for people to see her two new films—The Photograph, a heartfelt drama, and The Lovebirds, a romantic comedy slash murder mystery—the former of which shows little trace of Insecure’s Issa, the funny, self-conscious 20-something we all know and relate to so hard. That character will always be part of her. The series is, after all, loosely based on Rae’s semi-autobiographical web series The Misadventures of Awkward Black Girl, but she’s ready to show us just how multifaceted the real Issa Rae really is.

"I want to try different things and see what I can do,” she muses. "I don’t want to just play myself, so I want to be able to experiment. Some of the things that I have on the slate to actually act in are very different. I don’t want to get caught in a comfort zone. I don’t want anybody to be able to put me in a box.” 

The first step outside her comfort zone comes in The Photograph, a romantic drama that grapples with love, loss, grief, and family and features LaKeith Stanfield (Get Out, Uncut Gems), fittingly out this Valentine’s Day. But, Rae confesses, "I think people are just expecting me to be funny, and the character just lost her mom, so she’s going through it. Obviously, there are elements of humor within the movie, but that’s not the driving part of the character, which is new for me because I do lean on humor. It’s been a defense mechanism for a lot of my life. That’s my go-to, I guess, because my comfort zone is humor. So to not be able to lean on that in this film was interesting.


(Image credit: Taylor Rainbolt; STYLING: Flor et.al dress; Alessandra Rich earrings; Giuseppe Zanotti Lavina Metallic Platform Sandals ($895))

Over the course of our hour-long conversation, I learned that this tendency to challenge herself is how Issa operates best. Expansion, growth, self-discovery—these have always been her MO, but right now is an especially charged time for the Emmy-nominated actress, producer, and writer. She shared candidly, "This year will determine whether or not I have longevity on a particular side.” In that moment, I could sense this vulnerability bubbling up inside her. "If these movies do well,” she continued with more urgency, "then I’ll have more opportunities. If they don’t, I might not. But I’m not a person who puts all my eggs in one basket. I have too many baskets.

Continuing Insecure. Starring in back-to-back feature films. Launching a record label. Co-owning a coffee shop. Operating two production companies. Yeah, that’s a lot of baskets. What motivates a person to branch out in so many directions, I wondered. Are there moments when she bites off more than she can chew? Sure, but it all comes down to her objective to lift up those around her. "There’s a lot that I love to do,” she shared, her voice shifting into self-assuredness. "So I love being behind the scenes. I love producing. I love writing. I love business. We have a new record label, and even there, crafting other artists in an area where I’m weak—I can’t sing. I’m not a rapper. I’m not an artist, but to be able to work with people who have that talent and to lend what I know to help their careers is very exciting.”


(Image credit: Taylor Rainbolt; STYLING: Prabal Gurung top; Alessandra Rich Embellished Heart Drop Earrings ($369))

Raedio seeks to connect musical artists with film and TV projects, helping creators in one industry land opportunities in another. If you’ve been watching Insecure since day one, you know just how invested Rae is in the music world. Her Peabody Award–winning HBO series has featured independent and Los Angeles–based artists such as Saweetie, SZA, Blood Orange, and so many more, thanks in part to the Solange Knowles–curated soundtrack and Rae’s passion for spotlighting promising young talent.

When she launched Insecure in 2016, she took care to compose a team chock-full of creatives. Insecure is Insecure because of the producers, the cast, and the costume designer, all the way down to the soundtrack and the designers Issa wears in the show. It’s a show full of discovery. If you wanted a showcase of some of both the most prominent and on-the-rise talent in their respective fields, Insecure is it. A notable new addition to the set is Shiona Turini, a former fashion editor turned costume designer and all-around industry force. Turini was brought to the show in the middle of the last season, but the upcoming fourth season, Rae beamed, is where she really shines. "I trust her a lot,” she tells me. Turini has introduced Rae to countless new designers already, many of whom are black designers and some African designers too. "And I just love what she brings to the show because wardrobe plays such a huge part of these characters’ identities, and she understands that. She’s very in tune with the evolution of certain characters and what we’re going for.”

Rae’s mission to provide platforms to the people around her isn’t something that only occurs on the set of Insecure. It’s the driving force behind all of her endeavors, and the latest way she’s manifested this goal is by bringing to life the most democratic space of them all: a community-first coffee shop in her very own neighborhood of Inglewood. She tells me the decision to become a co-owner of Hilltop Coffee was immediate and something she desperately needed as a young creative who used to do all her writing in coffee shops. "Being in those spaces where you get to just see other people working—people who look just like you,” she muses, "there’s just nothing more empowering than that. That’s why I wanted to get involved. And then just the natural networking that happens there… I think a lot of these spaces—I think about Soho House or The Wing—these are all spaces that are meant to bring like-minded or, I would say, like-statused people together. We just don’t get those in our community.”


(Image credit: Taylor Rainbolt; STYLING: Valentino Dress; Alessandra Rich earrings)

Rae, I’m learning, is a yes woman. But the fact that, say, she doesn’t possess prior experience owning a coffee shop is hardly a deterrent. She says yes first and then figures out the logistics. "Oh, yeah. You’re right,” she says, mimicking her realization that she won’t always be able to run things by herself. "I’m not going to be grinding the beans and stuff. Cool.”

Grinding coffee beans may not be at the top of her résumé, but being a business owner is front and center. She helms two of her own production companies—Issa Rae Productions, which focuses on projects written by or starring her, and ColorCreative, co-founded with Insecure producer Deniese Davis, which works to give visibility to and create opportunities for women and minority film and TV writers. ColorCreative is her passion. When telling me about the work she does there to put emerging voices on the map, a mix of pride and passion takes over her. It’s immediately clear that the studio is the soul of her work. It’s personal—Rae herself was a young black girl from L.A.’s south side with dreams of her own—but it’s also political. There’s no denying that in Hollywood, white talent is the default.


(Image credit: Taylor Rainbolt; STYLING: Valentino Silk Trench Coat With Leather Details ($6900); Almasika Berceau Gold Hoop Earrings ($1600))

Sure, we've seen blockbusters like Crazy Rich Asians and Black Panther blow it out of the water, but they continue to be the exception, not the rule. According to UCLA’s most recent Hollywood Diversity Report, film writers of color are underrepresented five to one, making up just 7.8% of their industry.

"Since 2014, we've been discovering underrepresented writers and giving them various platforms or helping them get staffed, helping them get representation,” she explains. "And we’ve had so much success there just in terms of putting them on the radar for the industry. Getting them representation is no small feat so that they can get more jobs. That’s what I ultimately want my legacy to be.

Actor, writer, producer, music industry aficionado, coffee shop owner. As she continues to take on new acting roles and add to her ever-growing string of hyphenates, I’m convinced that there’s no project too intimidating and no role too foreign for Rae. If, by this April, she makes us laugh in Insecure, makes our hearts swell in The Photograph, and keeps us on edge in The Lovebirds, then I can only imagine what else she has up her sleeve in 2020—let alone the rest of the decade. 

Photographer: Taylor Rainbolt

Stylist: Jason Rembert

Hairstylist: Felicia Leatherwood 

Makeup Artist: Delina Medhin


Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.