What Insecure Fans May Not Know About Issa Rae

Issa Rae (born Jo-Issa Rae Diop) has evolved as a Hollywood bigwig since her 2016 HBO debut, establishing an empire and becoming a household name in the process. Best known for her HBO show, "Insecure," Rae is not only an actor, but also a writer, producer, and owner of multiple businesses. She has a production company, a record label, and a management company for diverse writers and content. Additionally, she has a multitude of non-media endeavors, including multiple coffee shops and a hair care line. She's even been a CoverGirl spokesperson (via Teen Vogue).

In addition to "Insecure," Rae's other acting credits include the films "Little," "The Photograph," and "The Lovebirds." Behind the lens, she has executive produced many programs, including "The Choir," "Sweet Life: Los Angeles," and "A Black Lady Sketch Show," and that's really just the beginning. With a huge development deal signed as of 2021, Rae has taken Tinseltown by storm — but success did not come overnight. Here are some things that "Insecure" fans may not know about Issa Rae. 

Issa Rae seems to have known her destiny early on, devoting her childhood to writing and the arts. At age 11, she wrote her first spec script for the sitcom "Cosby," which she patterned after an old "Moesha" script that she had once won at a live taping (per NPR). Shortly thereafter, Rae wrote a script for a new sitcom that she titled "Ronnie," and sent it to NBC. "I got those rejection letters fairly quickly," she joked in a Rolling Stone profile.

A few years later, she wrote a script and submitted to the ABC writers program, though she was ultimately unsuccessful due to the amount of profanity in her script (per Rolling Stone). And though it all started with writing, Rae started incorporating acting into her orbit in high school. She told Glamour magazine that she played the lead in school plays at the King/Drew Magnet High School of Medicine and Science four years in a row, and it was at Stanford University that she began to explore the idea of entertainment as a career. "I was like, 'Oh, I'm not as good at calculus as I thought I was,'" Rae told Rolling Stone. "For me, I found success in creating plays for black people, directing and adapting them. I don't even remember much about my grades. They were OK, but it was just really about creating a community and discovering my love for the arts."

Issa Rae first got famous for her web series, "The Misadventures of Awkward Black Girl," which focused on a girl named J and her self-conscious way of living life. The award-winning series came out in 2011, has millions of views on YouTube, and led to a book of the same name. "Someone told me I should call the series 'Awkward Girl', otherwise people would focus on the fact I'm Black," Rae told Vogue. "I wanted to create space for a character who is an awkward Black girl." The series went viral — thanks in part to a crowdfunding campaign that raised nearly $60,000 (per Rolling Stone) — and J (played by Rae) was the starting ground for what would later become the main "Insecure" character, Issa Dee.

"Awkward Black Girl" was not Rae's first foray into producing web content. In fact, it was her third series (via Harper's Bazaar). She started producing online content when she was a student at Stanford University, and her series, "Dorm Diaries," was a satire that focused on "what it was like to be Black" on her campus (per Bustle). It was not until "The Misadventures of Awkward Black Girl" that Rae stepped in front of the camera. "I was extremely terrified," she told Paper. "I'd seen the comments on people I'd featured, and they were mostly positive, but when I saw the negative ones I was like, 'Oof, glad that ain't me.' And so I put myself out there and it just felt different."

Like nearly everyone in Hollywood, Issa Rae has had her disappointments and misses. One of her big ones was her 2013 pilot, "I Hate L.A. Dudes," which was executive produced by "Grey's Anatomy" creator Shonda Rimes. According to GQ, ABC (where Rimes was producing all her content at the time) passed on the project when it was in development. Rae looks back at the pilot with a self-critical eye. "I was so focused on what I felt like fit their network that I didn't focus on the story I wanted to tell," she told The Hollywood Reporter in 2017. "I was eager to please and that made my voice kind of irrelevant, and the reason they brought me in the first place was to have something to say."

Clearly, Rae has developed her voice — of which the myriad awards "Insecure" has won can attest — and if the ABC opportunity had come through, the show may have never come to exist. "As soon as the ABC door shut, I got a call from [HBO executive] Casey Bloys to say, 'Hey, what else do you have? What other ideas do you have that you want to pitch to us?'," Rae explained in an interview with Assignment X. Drawing on some of the themes explored in her own "Misadventures of Awkward Black Girl," as well as classic Black sitcoms "A Different World" and "Living Single," Rae created "Insecure" with that inspiration in mind, and began her partnership with HBO.

Across many interviews, Issa Rae has discussed the self-doubt that has plagued her throughout various stages of her career. She told Glamour that her early lack of confidence was due to a lot of social comparison between herself and her peers. "The embarrassment came from making a YouTube series while all of my friends were being doctors, lawyers, diplomats, all of those different things," she said. "Those post-college questions — did I have to go to college to do this? Did I have to pay hundreds of thousands of dollars to make YouTube videos? — that was embarrassing for me."

Even though "Insecure" premiered to critical acclaim in 2016, Rae struggled with the idea that she'd exhausted her creative capabilities. She discussed her imposter syndrome with Yahoo! Entertainment in 2021, explaining how she ended up "pushing through it" by emboldening her collaborators, particularly women of color, and being "confident in what it is [she's] putting out there." 

Fortunately, Rae evolved a much more positive take on her capabilities. While she told Bustle in 2020 that she feels she has "so much more to do and so much more to prove," she's also expressed a comfort with the role she has earned in the industry. "At this point, no one is going to convince me I don't belong here," she once said at a LinkedIn-sponsored panel (via Los Angeles magazine).

Some showrunners want to milk the cow as long as it has milk to give, but Issa Rae is not one of them. "Insecure" will end with Season 5, which is currently airing. While that may seem like a short run, Rae has actually been thinking about the end of the show since Season 3 (per People). "I'm flattered that people think I'm an idiot for ending it," she told Vogue. "Without a doubt, it was mostly positive feedback and I'm going to miss the show. I'm glad and grateful that it's ending on our terms."

In an interview with Tamron Hall, Rae said the decision to end the series was a joint one between herself and executive producer Prentice Penny. They felt that five seasons was enough to tell the story they wanted to tell, and Rae seems proud that the show is going out on a high note. "Prentice and I are so grateful that HBO believed in our show from the beginning and kept faith in us to see our vision through the end," Rae told Deadline, adding, "We always planned to tell this story through five seasons, but we couldn't have made it this far without the tremendous support of our audience." 

Issa Rae is a creature of habit, and her strict routine may help explain her ability to remain productive even amidst a global pandemic that thrust the "Insecure" writing staff into an awkward Zoom writers' room. According Rolling Stone, Rae starts each weekday with a 4:20 a.m. walk, on which she listens to podcasts on her AirPods — though she admits that the routine only works when filming is not in session. "Waking up super early just makes me feel better," she told Self in a separate interview in September 2021.

Rae gave an even closer look at her daily routine in an April 2020 Vanity Fair interview, when she called early mornings her "sweet spot" and said she did a lot of work between 5:30 and 9:00 a.m., before even eating breakfast. She then works from 10:00 a.m. to 6:00 p.m., with certain activities relegated to certain dates. Those early morning workouts are key for Rae, who admitted to Vanity Fair that she always felt behind before them. "I was trying to keep up, so this makes me feel like at least I have a handle on what my day's going to be, and the working out aspect," she said. "I don't like coming home after a long day and feeling like, Oh, I still gotta move my body?"

As part of her routine, Issa Rae has crafted a schedule that allows certain days to be purely creative. While Tuesdays and Thursdays are for business meetings and other tasks, Rae told Vanity Fair that she reserves Monday, Wednesday, and Friday of each week for writing. "I can't be creative if I have a call scheduled at 1:30," she once admitted to the WSJ | Magazine. "I just obsess about the call — so I need the day to be completely clear."

Beyond needing uninterrupted time to write, Rae also needs a good space, which generally means getting away from the house. "I just like being productive in different spaces, and home really sucks the productivity out of me," she told Vanity Fair. She is also a fan of to-do lists, which she discussed in an interview with Nylon. Finally, she sees outsourcing as a key to her success. "I became an accidental business person," she told the same outlet, adding, "So hiring capable people has made it so that I am able to take that time to just be creative."

Issa Rae has been producing content for as long as she has been famous, but it was years before she formed Hoorae, a production company that encompasses digital, television, film, and music. The company, which is a rebrand of Rae's previous Issa Rae productions, was formed in September 2020. According to Rolling Stone, there is also "an events division" that had yet to be developed as of April 2021, but that Rae hoped would result in a soundstage at the company's Hyde Park offices in Los Angeles.

Rae also has a record label, Raedio, that she launched in 2019 as a partnership with Atlantic Records. Raedio has now become the music division of Hoorae, and its artists include TeaMarr, Josh Levi, and NCognita (per PR News Wire). Many from Raedio's roster of artists are featured on "Insecure," which makes for great synergy and an exciting platform for these up-and-coming musicians (per Billboard). Rae even has a line of playlists that mix her commentary with music from the show, called "Insecure Interludes."

Just a few months after starting up, Hoorae got a significant boost with Issa Rae's huge deal to continue her partnership with HBO. Announced in March 2021, the overall deal will have Rae developing projects for HBO, HBO Max, and Warner Bros. Television (Warner Media owns HBO), and gives HBO Max, Warner Bros. Pictures Group, and New Line a first look deal for feature film projects (per The Hollywood Reporter). "I'm thrilled to not only spread my creative wings with the network that makes all of my favorite series, but also to produce culturally resonant stories with new voices that incite exciting conversations via Hoorae's expanded relationship with all WarnerMedia platforms," Rae told THR.

The month after announcing her huge deal with Warner, Rae told Rolling Stone she had 22 movies and television series in development, with 16 of them being for HBO or HBO Max. This includes the HBO Max series "Rap Sh*t," a remake of "Set It Off" for New Line, and multiple projects for HBO — from the documentary "Seen & Heard" to a comedy based upon a podcast, "Nice White Parents" (per The Hollywood Reporter). Hoorae also has the final season of "Insecure" and Season 2 of "A Black Lady Sketch Show" in production at the network.

A casual viewer might think that the main love story of "Insecure" is Issa and Lawrence, but in actuality, it's the one between best friends Issa (Rae) and Molly (Yvonne Orji). Rae told Bust that she actually patterned this friendship after the one she has with her own real-life best friend. Sadly, Season 4 of "Insecure" had Issa and Molly going through a rough spot in their friendship, after a big fight at the end of Season 3. "You think the growing pains stop when you're 16, but really, they continue into adulthood and there's no guide book," Rae told the same outlet, adding, "Sometimes you think you need certain people in your life to grow and continue and that's not always the case."

Despite the rocky road that Issa and Molly are currently walking, the actors who portray the characters have a strong, unwavering bond. "We were cast as best friends, and we became real friends, very very fast friends," Rae told Entertainment Weekly. The two met in 2008, and they like each other so much that Orji told the EW she has trouble relaxing when their characters fight. And in an episode of the "Jemele Hill is Unbothered" podcast, Orji may have explained why they work so well. "Issa's the dopest person in the world. ... I like making people laugh, she enjoys laughing. We're the perfect yin to yang," she said, adding, "Issa's very smart and just so community-oriented. She wants to see everybody win. ... She's an easy person to love."

Issa Rae has repeatedly spoken about how she is committed to getting Black stories on the screen, and she is similarly excited about cultivating a community of diverse creators. In 2014, Rae and Deniese Davis co-founded the management company ColorCreative, which is focused on growing "opportunities for women and minority talent" in Hollywood.

According to Variety, one of Rae's protégés, Syreeta Singleton, came to work for her through ColorCreative and is now the showrunner and executive producer of the upcoming series "Rap Sh*t." "I think that's the magic of Issa. I don't know if there's a whole bunch of people that would have jumped Syreeta to showrunner [of "Rap Sh*t"], but she is ready and she's gonna crush it. And it takes people like Issa to say, 'Yeah, you've got next,'" Robin Thede ("A Black Lady Sketch Show") said about Rae. Rae told Refinery29 that she invents spaces for people of color to be creative because she does not feel she had those spaces back when she was a young talent.

"Insecure" is very much a tribute to South Los Angeles, and Issa Rae is an advocate for the real-life area. In 2016, Curbed Los Angeles published a map of shooting locations, which included Issa's then-apartment in Inglewood, a movie theatre in Crenshaw, and Issa's then-workplace in Leimert Park Village. "For me, it was growing up there, and living life, dating, making friends in those areas, and seeing those places on television, and seeing them being shot up or with drugs, and not knowing that to be my own experience, and wanting to show the different side of it," she told Assignment X. "That was extremely important to me."

Beyond shooting in South Los Angeles, Rae has made it her mission to support the area where she grew up (though she moved around, she reportedly grew up mostly in upscale View Park, per Bust). She is a proponent for Destination Crenshaw, a community project that is being developed to highlight arts and culture in the Black community using "open air public space" (per Self).

There was even a community focus behind Rae's 2020 partnership with American Express. "Anything that I can do to highlight and help the struggling small businesses, the struggling small Black businesses in particular in my neighborhood, I'm all for doing," she told POPSUGAR. In fact, she even co-owns a local business — multiple locations of Hilltop Coffee + Kitchen, including one in Inglewood and one in Eagle Rock (via Los Angeles Magazine).

Issa Rae is notoriously private about her personal life, especially her romantic relationship. She told Refinery29 that learned to keep her personal life to herself back to high school, and this quest for privacy seems to have intensified with fame, and when it comes to her relationship with now-husband Louis Diame. In fact, Rae's sole confirmation of her impending nuptials was an Essence photo where she wore her engagement ring (per Rolling Stone). "I just feel superprotective of any relationship I'm in," Rae told Rolling Stone. "That's come from observing and making fun of people over the years who broadcast the most intimate parts of their relationships, then are left with egg on their face. I call them the 'me and my boo' people."

Unsurprisingly, fans were taken aback when Rae posted her wedding photos on Instagram in July 2021 — though they were not surprised that she made a joke of the whole thing. Rae looked breathtaking in her custom Vera Wang dress, which she told Mic she "felt compelled to share" in order to control her own wedding narrative. "I still try to be private about my personal life, but that was something that I knew was going to be shared, and I just wanted to share it on my own terms," she told Self. Rae also opened up about children, explaining that she is unsure of whether she wants kids of her own, given her "window" of opportunity in Hollywood.