Issa Rae reflects on ‘Misadventures of Awkward Black Girl’: ‘It kind of had to be sh*tty’

Today marks the 10-year anniversary of the series that launched Rae's remarkable career

It’s hard to believe that it has been 10 years since Issa Rae launched her web series The Misadventures of Awkward Black Girl and unknowingly launched herself into super stardom. 

The comedy hit YouTube on February 3, 2011 and won a Shorty Award for Best Web Series the following year. The two-season show inspired Rae’s HBO series Insecure and shares a title with her 2015 book. 

Read More: ‘Insecure’ to end after season 5, Issa Rae announces

Issa Rae
(Photo by Steven Ferdman/Getty Images)

theGrio caught up with the woman who keeps on winning to find out how she’s reflecting on her start, dealing with the end of Insecure, and looking toward the future. 

“In some ways, it feels super fast,” she said of the decade-long career milestone. “I think this past year has really changed the concept of time for me. So it does feel like a different time. But in terms of where I am now and what I’m doing, it doesn’t feel that long ago at all.”

Rae recently announced that the upcoming season of Insecure will be its last.

“I feel like I just accomplished that web series and just started ‘Insecure.’ It’s hard to believe now ‘Insecure’ is coming to an end,” she continued. 

The groundbreaking HBO series has been a consistent success since it debuted in 2016 and it has launched so many incredible careers aside from its creator’s. 

(Photo: Merie W. Wallace/HBO)

Yvonne Orji, Natasha Rothwell, Tracy Oliver, and Amy Aniobi are just a few of the talented collaborators who got to shine through Rae’s work.

“As far as like ‘Awkward Black Girl’ and ‘Insecure’s’ impact in terms of launching other careers, I think that is to me the best part about both. I think to be able to create something that gave opportunities for other people and platforms for other people to launch and tell their own story is the best accomplishment.”

While fans are still coming to terms with the end of an era, it’s fitting that the series is wrapping when it’s predecessor turns 10.

“In the sense that it’s ending during this time when ‘Awkward Black Girl’ is on the tenth year, it does feel like a full circle moment. But it also feels like a next chapter for me. These are two pivotal things ending that are that sort of representative of who I am. They’re so much of my identity in some way.”

The Misadventures of Awkward Black Girl was born out of the lack of representation in Hollywood; a problem that persists, but has been tremendously impacted by her projects. 

Issa Rae
(Photo by Michael Loccisano/Getty Images for HBO)

“It was kind of a surprise was like in creating the show, and recording it, and editing it, and putting it out there…It was literally just me being an audience member and wanting to see what I wanted to see,” she explains.

I wanted to see the characters that were missing from the television screen. Once that first episode aired, especially compared to the other two web series that I had done, I was immediately aware that this was something different. People were taking this and celebrating it in a way that I had not anticipated. I knew enough to know that, OK, this is going to be a thing. I have to make sure that I follow this momentum. Of course, I didn’t imagine where it would take me but I knew that I had to get on it.” 

The series was shot with a small crew on a shoestring budget but that didn’t keep Rae from delivering multiple memorable moments. 

“I really love the dance episode on season 1, episode 5 because it was ode to the movies that influenced me like ‘Love and Basketball’ of course and even ‘Save the Last Dance.’ We had so much fun. I shot it at my friends house. It was still so small because we had a small crew and it looked really official, and it was the first time that I got to put the music that I love into the series,” she recalled.

“I was like, OK, I’m going to make this. I’m going to music supervise this and I’m putting Ice Cube in it even though it got blocked off of Youtube and Frank Ocean who I had just discovered at the time and it was fun. There are just so many moments that I remember that that felt fun to shoot and fun to edit. It looked beautiful to me.”

(Credit: Rae)

Ten years after the show’s premiere, Rae is making some of the most beautiful projects about us on the big and small screen and working with a lot more resources; a far cry from the days of shooting Awkward Black Girl and figuring it out as she went along.

“There are tons of cringe-y moments, are you kidding me? I can’t really rewatch the series. I used to early on, but I haven’t watched in so long just because there are just some technical things that are just wrong. Again I was editing and shooting a lot of it earlier on and was just doing things completely incorrectly that wouldn’t pass and or be forgiven now,” she said.

“So many of the elements are just bootleg. I am so grateful that people saw past that and really just embraced the story until we kind of got our shit together, which we did. Part of me also loves the scrappy element because if I had been a perfectionist, I would have never put it out. It kind of had to be sh*tty.” 


We’re all benefitting from Rae’s decision to go for it, and lucky she didn’t let her hangups stand in her way.

“I sat on that idea for two years and for me it was the fear that somebody else was going to do it and not have the excuses I did. And then all I would be saying ‘should’ve could’ve would’ve’ and I just could not bear the thought of missing out on an opportunity,” she explained.  

“I feel like so many of us have great ideas that we just sit on either out of fear and we come up with all these reasons why we can’t do it. Somebody absolutely is going to run with the idea that you have if you don’t. And if you’re fine with that then great. But as for me, I can’t live with that.”

Now that Insecure is coming to an end, Rae is setting her sights on her next adventures. 

“For me, there’s a scariness. What’s next? What else do I have to offer? What other parts of me am I mining for the future?” 

Issa Rae
PARK CITY, UTAH – JANUARY 24: Issa Rae attends the HERstory presented by Our Stories to Tell at Firewood on January 24, 2020 in Park City, Utah. (Photo by Michael Loccisano/Getty Images for HBO)

Read More: Issa Rae launches Masterclass on screenwriting, ‘finding your voice’

If she sounds a bit insecure about life after the series, don’t be too concerned. The award-winning actress, producer, and creator is still the same Awkward Black Girl we all fell in love with a decade ago.

“You never feel successful. You never feel like ‘I’m here. I made it.’ There were so many times that I was like, ‘Once I get money best believe I’m going to be stunting in all the fresh fashions all the time like you’re not going to be able to tell me nothing.’ Hollywood is such an illusion place and I was born and raised in L.A. When I moved away and came back, Hollywood just became something that felt so cool and unattainable. And then even being in it, I just felt like I didn’t belong, you know? It’s still taking me a while, 10 years later, to feel like, Ok…I have a place here,” she said.

“I didn’t come up through writer’s rooms. I wasn’t an actress at it a long time in different movies and discovered that way.  I kind of broke in through the back door. In that way, you just feel like, ‘I wasn’t invited to this party.’ For me, there’s always a feeling of discomfort. Shout out the people that made me feel welcome ad included me and really celebrated the journey.”

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