TV

Issa Rae Reflects on 10 Years Since Awkward Black Girl and Moving On from Insecure

Issa Rae’s iconic web series, The Misadventures of Awkward Black Girl, introduced a new type of Black girl to the cultural lexicon at the time we needed it most.

The show, which is celebrating its 10-year anniversary, having premiered on YouTube on this very day in 2011, quickly became a masterclass in authentically—and hilariously—portraying everyday Blackness on-screen. Spanning two seasons, the DIY show followed Rae’s character, J, in the most mundane situations, not limited to working a dead-end job, dating her first white boy, and navigating the utter chaos that makes up one’s 20s. An instant hit, it eventually led to the creation of her HBO series, Insecure, which is currently filming its fifth and final season.

With Awkward Black Girl and Insecure, Rae has changed the conversation about how Black women are portrayed in the entertainment sphere; rather than chasing perfection, she allows her characters to simply be unfiltered, unapologetic, and sometimes emotionally messy. Because of Rae’s trailblazing work—not to mention she’s transformed into an Emmy-nominated production powerhouse—she’s inspired a new generation of Black women who can now see more of their true selves reflected in their screens.

Ahead of The Misadventures of Awkward Black Girl’s 10-year anniversary (and virtual watch party, which Rae herself is hosting via her YouTube channel tonight), we spoke with Rae and reflected on her decade-long Hollywood journey, how both shows have shaped her voice as a creator, and why she’s more than ready to leave Insecure behind.

Let’s go back 10 years to when you ultimately decided that you were going to create the web series. Where were you in your life at that point in time, and what do you wish Issa knew then that you know now?

At that point, I was working in the nonprofit space. It was like corporate nonprofits, and I was simultaneously shooting my other web series, editing it, and doing videography work for wedding and talent shows. Just kind of finding ways to pay the bills while also trying to break into the industry via this second web series. Taking classes at UCLA, just trying to get better and learn about the business, taking night classes. It was just a time of just trying to figure out and get quote-unquote discovered. By the time I get Awkward Black Girl, I’ve been spending so much time trying to get these other two web series, I had been discovered, pitched to networks, and things like that. I mean, it’s just been shut down.

So by the time I put Awkward Black Girl out, it was kind of just like, “Fuck it, this is what I want to see on TV. Let me just put it out there, see what happens. I’m scared as hell, but I have to put this out, because I’ve been complaining so much about what I’m not seeing on TV and what I want to see. This is it, and once I put it out, I can go back to complaining.” So that’s kind of a snapshot of my life at that point.

Did you realize when you first put out the show that you were creating a character and a story that was going to resonate with so many people?

I hoped so, because I knew at least my friends could relate. They could relate to knowing that this was a representation of me, that we’ve had these moments where we laughed about together. For sure, my family, I’ve definitely had them in mind—my siblings—but the outside world, not so much. I hoped that people could identify with the awkward moments of someone driving up next to you in a car and repeatedly feeling like, “Oh, my God, do I have to keep saying hi to this person?” I just didn’t anticipate how many people would identify to the different elements of that episode.

The rapping part was such a last-minute addition, and it was based off of Nicki Minaj being so popular at the time. Her rapping style cracked me up. So, I was like, “What if this character also, in addition to being awkward, has this aggressive rapper side.” I was nervous about how stupid that would look putting that out, but I was like, “Whatever, it makes me laugh.” Yeah, it was terrifying, but I’m so glad people identified with the elements of that first episode.

While rewatching a bunch of episodes this weekend, it took me back to this moment in time where YouTube was king in terms of discovering new comedic talent and content creation. Did you feel that way?

Definitely. In some ways, I still think it makes me sad, because it was king for us during the time. I was 10 years younger, obviously, and people who were watching at the time were [also], but YouTube is still king for people that age and younger. Now I’m like, “Oh, did I grow out of that?” While I still create content for the web and things like that, I do kind of feel out of touch beyond TikTok, of just what the next wave of content creators … where they’ll be.

Exactly. I still don’t understand TikTok.

I’m so sad that I always vowed not to be one of those people that are just like, “I don’t get it. Not for me. Don’t care,” and I’m there. I’m not knocking anybody else who loves it. It’s just, I’m not there.

Much like how we’ve seen with Insecure, music plays a huge role in the series. For me, 2011 was a very weird time for music, whether it was pop, hip-hop, or anything in between. Are there any tracks featured on the show that you remember that you still have on heavy rotation today?

For sure anything Frank Ocean. I had discovered Frank Ocean via a friend. Actually one of the stars of my other web series, who’s a DJ, we were taking a road trip somewhere, and he was like, “I think you would fuck with this artist.” I was like, “Well, I’ll be the judge of that.” And then he started playing “Novacane” in the car, and I was like, “Who? What?”

I was just in love immediately, and then “Thinkin Bout You” came out, and I put that in an episode too. Even for the theme song for Awkward Black Girl—my brother’s a rapper and a music producer, and I asked him [to produce the song]. I was like, “I have this kind of jingle that I have in my head for the theme song of Awkward Black Girl, but I can’t articulate it.” I was like, “It has like a Mr. Sandman vibe,” and he was like, “Okay, whatever.” Then he just delivered this piece of music that was perfect. I was like, “You got inside my head, you’re the best.” Of course, it became the theme song. I just thought he was a genius for being able to translate my vibe.

Then when I really got to incorporate music, it was more an homage to the other movies that I love. Like Save the Last Dance and even other YouTube stuff. Back then early on, if you put unlicensed music [in YouTube videos], then your shit would get blocked. So I had to be very sparing in terms of, this episode needs it, I don’t care if it gets blocked. I’m scoring it anyway. It was definitely a highlight of being able to put real music into the series.

The funniest moment for me was when J goes on her first “white date” and she comes down the stairs in a prom dress to Sixpence None the Richer’s “Kiss Me.”

Oh, that’s right! That’s a good song, everything with that She’s All That era and that white ’90s theme music that all came out of those years. It was just untouched! The movies, the music? Incredible.

How has your creative process changed, if at all, since your Awkward Black Girl days to now? Because as I imagine, what you were doing then is very different from working with HBO the last few years.

Without a doubt. I mean, it’s definitely been formalized, and I think that happened early on. Those first three or four episodes, I was just kind of piecing them together. The script wasn’t in traditional script format, and it wasn’t until my friend came on board, Tracy Oliver. She went to USC’s producers program, is a writer, and was an aspiring writer as well. She was like, “Girl, you got to do this seriously. You have to do this for real, put the script in a real format and treat it like a real production.” Then she recognized all the hats that I was wearing and was just like, “What if we started a writers room?” We know a girl from Stanford that we could ask, and then we found another writer, and then we had a mini writers [room] among the four of us for the episodes moving forward.

I had no idea that that was preparing me in some ways to work on Insecure. This was a show that I felt like it was mine and I was extremely collaborative, but it was also fulfilling to have other people contribute their ideas. I wasn’t really used to that beyond a writer due, but working with the four of them, navigating pitches, taking suggestions, and things like that was preparing me in the best way for the future. I definitely credit Tracy with that.

Then, of course, with the HBO machine, you’re getting way more voices on an official level, and they’re telling you when it’s ready to go. I think the difference with creating something online, obviously, is that you can decide like, “This is ready to go. This is about the air.” To have executives be like, “Oh, no, no, no. You got about, like, eight more drafts before this is right,” is daunting, but I’m so happy with the version that ended up on-screen.

What are some of your fondest or just funniest memories from creating the web series?

Just how scrappy it was. I didn’t know shit, I didn’t have access to shit, I didn’t have access to casting. I would get everything off of Craigslist. So finding the actress to play Boss Lady was a Craigslist ad and three white women responded. The first two were like, “What the fuck is this?” And the third one was like, “Okay. Yeah, sure.” She ended up being great.

Even the first session of [me and Sujata Day] shooting was me jumping back and forth between the camera to shoot the hallway scene, and I was conscious of her time. I’m like, “I have a real actress. So I have to make this professional and not waste her time.” So I was rushing to shoot it and stuff like that. We became really great friends after the process that she had to tell me like, “This shit was fucking insane, but I’m so glad I did it.” Moments like that and just having the trust, the people involved, and really just them being so down to make it great—there’s just no better feeling than that. I will always feel a sense of gratitude and indebted to them or the care they took in the series.

You’re about to enter Insecure‘s fifth and final season. How are you feeling right now with another major chapter of your career and your life soon coming to a close? Are you ready to say goodbye? Are you feeling relieved? What’s your head space right now?

I’ve definitely been ready to say goodbye. Working on the end of the series and realizing that I’m in the 10th anniversary of ABG, it’s left me to stop and think, “What’s next for me?” So, in that way, I’ve been so eager to finish the show.

I’ve given so much of myself, and I know that I don’t want to be in another television show that I’ve created, just because it’s so daunting, and it takes so much of your time. I am just kind of trying to figure out balancing the business side and being behind the scenes with how much I actually want to be in front of the camera. I’m figuring that out, and I feel like I’m at another terrifying crossroads of what’s next.

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Rewatching Awkward Black Girl, then obviously being a long-time viewer of Insecure, I can’t help but notice how much these characters stem from your life and your everyday experiences. It makes me think, “Damn, is she tired of this? Does she not want to give us this anymore?”

It is, and with Awkward Black Girl, I was for sure tired of it by the time I created Insecure, because it felt like that was a specific story and a specific time in my life. It also took a lot of time, and I wasn’t able to do other things. Now with Insecure, I started conceptualizing it when I was 27, 28. I think the first draft, I think the character says, “I’m 27,” and then because it was a two-year development process, became 29 and it became that. I’m like, “I’m 36 now, what do I look like playing a 32-year-old or a 30, 31-year-old forever?”

Obviously, the show could grow and the characters can get older, but it just feels like a specific part of my life that I feel like is done. The entire reasoning behind Insecure is to show that this journey to these characters becoming secure in themselves and becoming comfortable being uncomfortable. So, in that way, I’m ready to move on to the next story, but I don’t know what part of myself I’m giving for the next project. Maybe that’ll come years from now. Who knows, but I definitely don’t have it now.

I knew as soon as you made that announcement and you were like, “It’s a wrap.” I thought, Yeah, she’s done.

You are correct!

So much of your career has been focused showcasing Black people and Black culture, and without making the story solely about Blackness. Regardless of what road you go down next, is that something we’re going to continue to see in your work post-Insecure?

Without a doubt. I mean, that’s what I love to see. Obviously, I’ve continued to produce things that are not my work, and that’s also an exciting part. I love grounded, real stories that are conversation starters, that are extremely relatable and sometimes frightening. I love being able to see myself and people, and use the people that I know—whether they like it or not—in stories. There’s just so much there for me that you hold on to, or that I hold on to like that.

This interview has been edited and condensed for clarity.

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