Issa Rae rarely turns a bad look. She’s styled for the June issue of Vanity Fair by Shiona Turini, the costume designer on Insecure, Issa’s HBO show in which she appears equality well dressed — all the time. I’m not crazy about the belt she’s wearing on the cover, but I’m here for literally everything else especially this blue suit from Robert Wun.


The futuristic ensemble is from Robert’s AW 2021 collection, Armour. His eponymous label celebrates the female form and this latest collection is a tribute to his grandmother, who passed away last year. Every look is named after a woman in his life who’s inspired him. Issa’s wearing the Zhong Lin suit and as I’ve learned, Zhong’s a self-taught Malaysian photographer known for surreal and striking portraits of women. 


How poetic for Issa, a woman who’s successfully parlayed a self-produced web-series into an Emmy-winning HBO show, to be styled in this gorgeous suit named after a self-taught photographer who’s become internationally renowned for her creative lens. This styling is layered — pun intended. 

Issa’s on the cover of VF ahead of Insecure’s final season. Her game-changing HBO series is wrapping after its fifth season airs later this year. Issa explains she’s feeling season one pressure as they ready their final bow because their fanbase has grown every season and swelled quite dramatically after being discovered by many during quarantine bingeing. She actually rewatched the entire series as they were writing this season and because they’ve been shooting different scenes from multiple episodes out of order (to ensure production is COVID compliant) there was a point where she was questioning what was ending up on tape: Is it any good? But don’t most creatives have those doubts most of the time? As a fan, all I’m hearing is that she’s keeping the bar high right until the end. 

Unsurprisingly, Issa is more than ready to call curtains on her baby. As the creator and star, she’s also been producer and writer for all five seasons, consuming her schedule for a large chunk of the year thanks to the writers room, production, editing, and promo. It’s a position she says she’ll never put herself in again, but being her first Hollywood project she didn’t know any better. Now, she’s looking forward to having more time to work on a variety of projects because, as she tells Vanity Fair, she feels like she hasn’t done anything. HAHA… right? “I have one web series, one show,” she says. “I haven’t even written a movie. Of the sh-t that’s mine, I don’t have much.” Fair enough. She does explain that she’s lining up more film and TV roles because she’s eager to polish her acting chops, but she’s equally focused on projects to write and produce herself so she can tell stories from her perspective — have more sh-t that’s hers. 


Yesterday, HBO Max announced her next project will be Sweet Life: Los Angeles, a reality series following a group of young, strong-willed, ambitious Black friends in southern LA (Issa herself grew up in Inglewood) as they pursue their dreams. This project appears to be the first of an overall production deal with HBO’s parent company WarnerMedia, worth a reported $40 million. Issa Rae’s about to be the Tyler Perry of HBO with her upcoming docuseries about Black television, Seen & Heard, and comedy series, Rap Sh-t, loosely based off female rap group City Girls, among previously announced projects for the network.

A common theme in all of Issa’s many projects project going forward is celebrating stories from her community and uplifting creatives of colour and female filmmakers. That’s why the news that she’s being brought on as an executive producer and mentor on the revival of Matt Damon and Ben Affleck’s HBO docuseries Project Greenlight is so interesting to me. You may remember in the show’s last season, which aired in 2015, Matt Damon whitesplained diversity to producer Effie Brown, who raised the point that the casting for the series should have been more inclusive. In their back and forth, Matt tells her, “When we’re talking about diversity, you do it in the casting of the film, not in the casting of the show”. Clearly stunned, Brown (the only Black person in the room) responds, “Wow”. When the episode aired, Matt apologized in response to the backlash.



The Issa-helmed reboot doesn’t involve Damon or Affleck and will focus on the next generation of female filmmakers who are given the chance to direct a feature film. Issa tells VF, she’s excited about this version of the show making filmmaking feel more accessible. The film finished through the docuseries will then premiere on HBO Max. 

One highly anticipated project that’s apparently fallen off the docket completely is the Issa penned, Ava DuVernay directed, Netflix spy thriller starring Rihanna and Lupita Nyong’o, inspired by Twitter’s response to a photo of Ri and Lupita sitting side by side at a fashion show. Issa admits the four of them did end up connecting on a group chat, but all these years later, “Zero comment! Nothing has changed”.