It’s been a busy and landmark year for internet phenomenon Issa Rae. She’s been featured on Totally Biased with Kamau Bell, producing and promoting her award winning series Awkward Black Girl, now in its second season on the I Am Other YouTube channel. She recently partnered with Shonda Rhimes (Grey’s Anatomy) and sold a sitcom to ABC. She even had the honor of sitting down with our very own Stephen and Patrick to discuss her success with Awkward Black Girl and love of Ryan Gosling:

This time, the ever-gracious and seriously funny Issa took time to speak with me for our own awkward meeting of the minds where we discuss earrings, writing, stereotypes, and the best ways to bust that gut.

Courtney Jones: You’re everywhere these days, The New York Times, Totally Biased, Rolling Stone, and CNN. You’re out there and people really seem to like you and what you’re doing. How do you self promote without it becoming tiresome to others?

Issa Rae: Yeah it’s hard. I wish I had the answer to that. I see that there’s this whole hipster thing happening where the less people who know about you, the more appreciated you are. The more people know, the more hated you are. It’s hard to try to find that balance. I am starting to see a shift, and I very much hate promoting myself, but when you’re online it’s something you have to do and I’ve gotten used to it. But I think it’s a matter of how it’s presented. People can always tell if it’s completely blatant self-promotion and nobody likes your content, or nobody likes you, then it’s hard to promote yourself. So, it’s helpful if you’re somewhat likable. So, I don’t know, I walk that line all the time. I don’t want to be obnoxious.

CJ: You are not at all! So tell me, where do you get your amazing earrings?

IR: Thank you for noticing!

CJ: They’re fantastic.

IR: Thank you. Sometimes I buy them. Sometimes they’re given to me. But I also have this amazing stylist friend. We went to high school together. His name is Chris, but he goes by Seth Brundel. He’s hooked me up with some amazing earrings.

CJ: Well, they look amazing. I just cut off my hair so I’m constantly looking for more earrings.

IR: Yes! It’s so essential. They’re ornamental.

CJ: Exactly. They draw the interest of the eye. Moving on, I recently read this quote from John Cho saying that stereotypes continue to evolve, and that minorities have to be ever cautious to updated stereotypes. What do you think about that? What do creators have to do to evade creating reactionary stereotypes to the older more staid ones?

IR: I think they just have to create things that are true to one’s self. The more that you try to create something that you’re not familiar with, the more tainted and obviously contrived it is. So I think that’s an issue. Even with this archetype of Awkward Black Girl, it wouldn’t work if I didn’t feel awkward, or if I was trying to write for someone else. So it’s essential to really write from a place you know. I’m very big on that. Write what you know.

CJ: Congratulations are in order on selling your sitcom to ABC with Shonda Rhimes. That’s a huge step, leap, really, and you have a lot of people cheering for you. So in light of that being a really good job, Jay the protagonist of Awkward Black Girl hates her job. Have you ever had a really bad job? What was the worst job you’ve ever had?

IR: Several. The worst job I ever had was simultaneously the worst and the best job I ever had. I was the docent at an exhibit for African American history. It was awesome because I got to learn a lot more about my history and it was an amazing exhibit. But it sucked because I worked with certain people who just didn’t get along; black people promoting black culture, who kind of hated each other. They put me in the slave ship section. It was the most depressing section in the world. I would have to spew these slave facts all the time and be all serious, and it was dark and cold. It was the worst. I spent my day in a cave. I actually spoofed the job in one of our latest videos.

CJ: That was really, really hilarious. So do you prefer to be in front of the camera or behind it? We talk a lot about multi-hyphenates. It seems like the era of the multi-hyphenate. What do you prefer? Director/Producer/Actor? How do you define yourself? Or do you define yourself?

IR: I don’t. I like it to shift, and I find myself giving a different answer every time. I think at the end of the day I love what comes easiest to me, and the most natural. Sometimes I feel like I just want to write and I can’t do it justice through acting. I definitely love directing, either way. I’m always directing something, if it’s my vision. But then there are days where I love to be directed. I love to be directed as an actress to be someone else, to really try to immerse myself in a different character. But I’m always learning, on every end. Learning how to be a good producer, better director, better actress. Anything that allows me to better myself, I love.

CJ: So you mentioned working with people you didn’t get along with while you worked on a slave ship exhibit. What’s it like to work with close friends and family members? I know you worked with your brother on your web series Fly Guys Present the F Word. Do you have any advice for people working with people they’re close with?

IR: Do it if you can. If you feel like you have a great relationship with your friends where there’s a mutual respect and they don’t mind you telling them what to do and you guys communicate well, then work with you friends. If you don’t, then don’t work with them, same with family. My brother and I working on this other web series, we have a great relationship, but we definitely had a falling out several times, like brothers and sisters do. But then the advantage of being family in our case is that they forgive you and move on. I think it really just depends on the type of person you are. How comfortable you feel expressing yourself, because that is key. You’re always going to have to be open and speak your mind in working with people in general.

CJ: What’s one question you’re tired of people asking, and one question you wish people would ask you?

IR: These questions are awesome, FYI. The question I’m definitely tired of is, “how and why did I create Awkward Black Girl.” I think I hate that question with a passion now. I wish people would ask more fun questions, like these, more questions about my personality. I wish more people would also ask more questions about the cast and the people who are involved in making ABG what it is.

CJ: Well on that note, can you tell me more about the “Bust That Gut” video and how amazing it is? Literally that song is stuck in my head all the time.

IR: You have no idea how happy Ricky Woznichak, who plays Temp Jerry, would be to hear that.

CJ: He’s hilarious.

IR: Yes! He really, really is. He’s so funny, and so enthusiastic about life and being apart of this show. The video was all his idea. He came up with the concept, and came up with the song after hearing “Climax” on the radio one day. We had them all improvise their lines that episode (“The Jingle”). He came in and was like, “I heard the most perfect song on the radio, you guys. And I’m going to base the jingle off of it.” And I said, “All right, do you.” So literally them getting up to perform it in the office, nobody could keep a straight face, because it was the perfect combination of people to perform that song. Then Shea [William Vanderpoort], who directs the show, he directed the video. And I had no idea they were going to go all out with it, because my vision, and thank God they didn’t go with it, was to do a really bootleg, homemade video, which they still did, but it was much better.

CJ: One of the YouTube comments on the video was that it reminded them of an MIA video. And I was like this is exactly what I thought of when I saw it for the first time. It’s incredible.

IR: That’s so funny, because they were so excited about that comment as well.

CJ: So I know you’ve been changing and expanding your cast and crew as you’ve been going along. Can you tell me a little about that process of choosing people for your team?

IR: Well, for the most part the crew has increased. For season two in the crew we kept the same people on board, then we’ve been able to bring more people on, script supervisor, extra camera men, things like that. The crew is amazing. Every time someone visits the set, either an interviewer, or an extra, they realize that and appreciate the crew’s dynamic. Because they all love being there and work so hard. They’re really efficient, and it’s a really fun environment on set. On that end, I couldn’t be happier with who we have. And then for the cast, anybody who joins walks into a family set. Sadly we have lost some, because life happens, and this isn’t anybody’s full time job. So we have to work around some of those people. When people have to travel for work or things like that, and it does affect the story. Which sucks. Like, Germy Patty [Kiki J. Harris], for instance, is a consultant. She has a legitimate job that she has to travel for during the week. And sometimes we have to nix certain story lines to accommodate schedules. So that’s the biggest challenge of Awkward Black Girl.

CJ: Yeah, but to fair, that’s like any film or TV show. They’re always working around the schedules of busy working actors. So I don’t feel like it hurts or negatively impacts your show. And when your staff and the people behind the scenes know what they’re doing, then it’s something that can easily be overcome. I think you do that very well.

IR: Thank you.

CJ: One last question. You’re really great about giving shout outs and props to people you’re fascinated by, like Stan Lee and Felicia Day in your latest Ratchet Piece Theater video. Is there anyone else you’d like to mention that’s up and coming or people whose work you enjoy or inspires you?

IR: Yeah. I’d love to give a shout out to Black and Sexy TV. They’re really, really awesome, and I admire what they’re doing. I’ve been following them for a while, even before I created ABG. I saw A Good Day to be Black and Sexy. Al Thompson is another person who’s been getting a lot of press recently, but you don’t get to see a lot of his work. His series is launching in the fall. But he’s done so much in the digital space, and I really admire his work ethic, because he’s always working on something new and the production quality of his stuff is amazing. Really, I love anybody who had the courage to just start. I’m watching a lot of web series, like The Unwritten Rules is a good one. I have also got to shout out the Got 2 B Real Diva Variety Show cracks me the fuck up any time I see it. The woman who writes that chooses to remain anonymous. Anyone who refuses to come out the woodwork and admit “Hey, I’m the genius behind this” is really admirable. She’s hilarious.

CJ: That’s awesome. I’ll have to check it out. Well thank you so much. I really, really appreciate you doing this.

IR: Thank you! Thanks for these awesome questions.

To keep up with Issa’s upcoming projects visit her website,, follow her on Twitter, @issarae, or check out her YouTube channel here.

Courtney Jones is a writer and book reviewer in Chicago(land). Follow her on Twitter @shymoxie.