10 Years After ‘Awkward Black Girl,’ Issa Rae Reflects On The Table She’s Built

With the landmark anniversary and the final season of “Insecure” announced, Rae is about to start a new chapter.
It's been 10 eventful years since Issa Rae uploaded the first "Misadventures of Awkward Black Girl" web series episode to YouTube. She about to wrap up her HBO series, "Insecure."
It's been 10 eventful years since Issa Rae uploaded the first "Misadventures of Awkward Black Girl" web series episode to YouTube. She about to wrap up her HBO series, "Insecure."
VALERIE MACON/AFP via Getty Images

Issa Rae laid the first brick of her empire exactly one decade ago with a melancholy declaration: “I’m awkward and Black.”

The writer/producer/actor didn’t know then, of course, that she was about to revolutionize Hollywood when she put a spotlight on a segment of Black folks who also identified as awkward. Rae, who was born in Los Angeles and raise partly in Potomac, Maryland, was tired of waiting for a green light from an industry that refused to prioritize Black stories. She was tired of seeing the women competing for Flavor Flav’s love on VH1 be among the only representations of Black women she saw on TV.

So she did something about it.

On Feb. 3, 2011, she uploaded the first episode of “The Misadventures of Awkward Black Girl” to YouTube. The web series, created by and starring Rae, followed J, a Black woman who finds herself in embarrassingly awkward positions in love, work and life. It ran for two seasons and existed as more than just a show on YouTube. It became the foundation of her Peabody Award-winning show, “Insecure.”

The cast of Issa Rae's "Awkward Black Girl" web series.
The cast of Issa Rae's "Awkward Black Girl" web series.
Isaac Matthew White

Rae told HuffPost that, even though it’s been 10 years, she feels as if she’s just getting started in a lot of ways.

“Ten years is a long-ass time, and to look back and think about where I started and just where I wanted to be, I feel like I’m beyond where I imagined,” she said. “But being in it now, I’m, like, ‘Oh, I have so much more to do.’ I don’t feel as accomplished as I want to be. I think it’s operating in the moving goal post mode, and seeing that ‘Awkward Black Girl’ was 10 years ago has forced me to stop and be, like, ‘Oh, yeah. I’ve done a lot of what I wanted to do.’”

That includes creating a show for awkward Black folks to see themselves reflected, fostering an online community of creatives and forging a path for her work to live on the big screen.

Though “Awkward Black Girl” premiered in 2011, Rae got the idea in 2008 while she was living in New York City. Conceived as an animated series, she sat on it, initially, due to a lack of funds and resources. She moved back to Los Angeles after two years in New York and soon after began working on her second web series (her first, “Dorm Diaries,” chronicled the life of Black students at Stanford, where she majored in African American studies ) with her brother and his music group, called “The Fly Guys Presents the F Word” in 2009. It wasn’t until an article on TheGrio titled “Where’s the Black version of Liz Lemon?” that she decided to move forward on “Awkward Black Girl.”

“I had to see an article asking the question about representation to get started, to light fire up under my ass, stop making excuses and finally just hit up, like, my best friend and my homie to do it, and to shoot it, and at least put it out there,” she said. “But I definitely didn’t have a plan. It was just, like, I have access to my dad’s clinic. I can shoot some scenes there. I had my own apartment, and I have a car and let’s see where that goes.”

Rae didn’t have contacts in the entertainment industry. She had a “Moesha” script she’d won in a contest when she was younger that she based her scripts off of. She also received some unhelpful advice from a distant cousin and some colleagues. It became evident that she had to figure a lot out on her own. A college friend helped her get a crew. Along with Rae, Chas Jackson, Tracy Oliver, O.C. Smith and Amy Aniobi (who later wrote for “Insecure”) made up the “Awkward Black Girl” writers’ room. As things got up and running, others reached out offering help with sound, lighting and other things that made the show noticeably better as the first season progressed.

Some of the cast and crew of "Awkward Black Girl."
Some of the cast and crew of "Awkward Black Girl."
Courtesy of Issa Rae Productions

“Community was absolutely everything. It is everything,” Rae said. “There were so many examples of even just down to the cast. People give actors shit, but I wasn’t a professional by any means. So to have people come in who elevate the show in that way and make it realistic, and then donating time, and time in a lot of those cases, that matters.”

Creating a mutually beneficial relationship with her community was a priority for Rae then and it remains one now as her star ascends. After creating “Awkward Black Girl,” Rae created ColorCreative alongside Deniese Davis to help diverse, emerging storytellers gain experience and visibility. It remains active today.

“I think now, especially, I constantly pack into the community around me obviously down to the writers on ‘Insecure,’” she said. “That’s just not something that’s going anywhere for me. I take a lot of pride in, like, the community we built in Hollywood, ’cause it feels real.”

The first season of “Awkward Black Girl” wasn’t just viral, it was culturally impactful. So much so that it caught songwriter/producer Pharrell’s attention. He came on as executive producer in the second season, and the episodes were housed on his YouTube channel, I Am Other.

In the past decade, “Awkward Black Girl” has amassed more than 19 million views and counting. In more recent years, fans have turned the comment section into a place to celebrate the strides Rae has made and reminisce about what the web series meant for them when they first discovered it in college, in middle school, at work.

Mayah D. commented four years ago, “I watched this show when I was in 8th grade, now I’m in college... And now she’s on HBO.. I loved her ever since!” That same year, Alidi13 wrote “In 5 years, your life can change so much; this is an inspiration! I remember watching this for the first time, now I’m re-watching it in awe of how Issa Rae blew up. Amazing!”

She knows how much the community she didn’t see played a part in her success. “I just really want to reiterate how thankful I am for not only everybody who watched and shared the show and still claim themselves as awkward Black girls, awkward Black people, but I have to acknowledge the people who are a part of this process and part of making this show possible,” she said. “I get a lot of the credit for doing it on my own, but it would not have happened if I didn’t have an amazing cast and crew and producers to help me along the way.”

The series finale of “Awkward Black Girl” was released on Feb. 28, 2013. The last episode teased the possibility of a film. And though everyone knows that’s not how the story ended, the rejections Rae continued to face in Hollywood, even after creating a hit series, made her wonder if she had already served her purpose with J’s story.

“Maybe that’s it and that’s my purpose, was to inspire other creators because it grew. This was kind of crazy,” she said, admitting how hard it was for her at the time. Some passed on her idea outright. Others in the industry just wanted more “Awkward Black Girl,” but Rae had already told that story. In 2012, news dropped that Rae had teamed up with Shonda Rhimes to create a show called “I Hate LA Dudes.” But ABC passed on the pilot, which Rae said “devastated” her.

“After that show was passed on, I felt like that was my one chance and I blew it, and I was ready to just be, like, ‘OK, well, I can go back to trying to make web series and trying to prove that I have an audience elsewhere,’ but I knew that I’d be exhausted,” she said.

Fortunately, Rae got the big break she had been working for when she struck a deal with HBO.

From directing church plays (titled “The Old and The Restless”) as a kid to creating an award-winning web series to earning a Peabody Award for “Insecure,” Rae’s path has always been ordained. Now she has her own production company (Hoorae), a record label (Raedio), a seat on the TV Academy Executive Committee and a forthcoming final season of “Insecure” that everyone is waiting for with bated breath.

With “Awkward Black Girl,” she bet on herself — and her community — when no one else did and won big.

Issa Rae acts out a scene for "The Misadventures of Awkward Black Girl" in August 2012 at J.E.T Studios in North Hollywood.
Issa Rae acts out a scene for "The Misadventures of Awkward Black Girl" in August 2012 at J.E.T Studios in North Hollywood.
Bret Hartman For The Washington Post via Getty Images

Though a natural-born griot, Rae told HuffPost that transforming the table she built with her web series into an empire wasn’t planned to a T.

“The only thing that I would say is intentional is just trying to showcase this archetype and this representation that I felt was modeled after me and my friends and doing my part, because I was feeling a lot of complaining about what I wasn’t seeing,” she explained. “And I guess the other thing that was intentional was I was editing and directing and just trying to create content at the time and trying to brand myself as someone who could do that.”

As Rae works on the finale season of “Insecure,” while celebrating a milestone with “Awkward Black Girl,” she feels as if she’s closing a chapter and starting a new one. She’s grateful, but closing out “Insecure” in the midst of a pandemic wasn’t what she expected. Rae admits that writing in the pandemic “was already bad enough,” but shooting also has had its challenges. Ironically, they couldn’t film for a week not due to COVID-19, but to rain in L.A.

“I think a week and a half ago, and I was super excited, and it just feels different because it’s, like, ‘Oh, this is the last season. It’s the first time I’m really enjoying every moment and trying to savor it,’” she said. “My colleague was, like, savor every part of this process because this is it. And that really changed my mindset. I don’t feel stress on set. So in that way, it’s beautiful. But I just, I want to get it done. I want to shoot it.”

She’s glad to be putting the show to rest the way she and showrunner Prentice Penny envisioned. Without giving any spoilers, Rae explained that the last season would be dedicated to exploring legacy.

“It explores the choices that we all make,” she said. “And that’s a big part of it. The living in the decisions that you make, the choices that you make, and owning those.”

She admitted that she’s scared about what’s to come.

“I’m back to feeling like, OK, will I have longevity past this? I’m creating my next show. And, you know, it matters if that show is successful. That’ll prove if I’m going to have longevity in this field, but it feels like I’m always putting myself through these tests. But, yeah, I’m entering into the next chapter and my next phase. I had a web series. I have a TV show. Kind of what else can I do? And how else can I have an impact? And I don’t know. I don’t know the answer to that.”

What she does know is that she has work to do. Rae is currently casting for her next show while she continues to have a hand in multiple projects. She’s excited about working with Jazmine Sullivan to create a visual treatment for her latest EP, “Heaux Tales.” She’s also eager to explore other genres. Horror is on her radar. When asked what she wants her legacy to be, she kept it simple:

“I just want to be known as someone who was passionate about the work and passionate about her people. I think I’m fine if that’s all you know.”

Hoorae will host a watch party of The Misadventures of Awkward Black Girl beginning Wednesday, Feb. 3, at 5:30 p.m. PST on Issa Rae Presents YouTube channel.

Correction: This story has been updated to state that the church play Rae directed was named “The Old and The Restless.” It has also been revised to note that she created ColorCreative after “Awkward Black Girl,” not prior.

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