The Awkward Ascent Of “The Misadventures Of Awkward Black Girl”

Backed by Pharrell Williams for a second season, Issa Rae’s YouTube hit The Misadventures of Awkward Black Girl gets ever more awkwardly popular.

The Awkward Ascent Of “The Misadventures Of Awkward Black Girl”

Although she comes across rather cool and composed in person, Issa Rae will be the first to tell you that she basically is Awkward Black Girl.


“Running into someone multiple times per day in the hallway is something I’m uncomfortable with. It gives me anxiety,” Rae says.

Fortunately for her, the outlet she created to channel her most mortifying moments has only gained in popularity since debuting in the spring of 2011. The web series Misadventures of Awkward Black Girl has racked up millions of YouTube hits, found a celebrity champion in Pharrell Williams, and has even started screening in AMC movie theaters. Of course, all the attention has also brought the filmmaker more things to feel awkward about.

Rae’s discomfort threshold was perhaps initially challenged upon trading a childhood home in Maryland, where she’d enjoyed a diverse group of friends, for Los Angeles and a predominately black middle school. The impact of that disruption stayed with her. Years later, while studying film writing in college, she would draw from her experiences as a black student at Stanford for her first web series, Dorm Diaries.

The Office-style college mockumentary was shot on essentially zero budget while she was still in school. It quickly made its way around campus through friends, and then on to other colleges. For her next web series, The ‘F’ Word, Rae took the focus off of her own experiences, and followed around a fictional group of musicians trying to catch a break. She made six seasons of The ‘F’ Word before deciding to get back to something more personal.


The Misadventures of Awkward Black Girl is Issa Rae’s mission statement. It’s a look at the cringe-making moments haunting everyday life, as seen through the eyes of a young black female protagonist–a rare point of view in web comedy. Rae plays main character J as someone who is stuck in a meaningless job with a less-than-satisfactory love life who occasionally vents her frustrations by composing totally inappropriate hip-hop lyrics.

“I love the specific kind of humor in Curb Your Enthusiasm and Parks and Rec, and I never saw it in shows of color,” Rae says. “I just wanted to create a character that I could relate to, and that I find funny.”

A lot of other people found J funny too. The audience from Rae’s first two series carried over to the new one, so she had a 10,000-person subscriber base on Awkward Black Girl right from the beginning. She’d made some mistakes with the first two series as well, which she now knew how to avoid.

“People aren’t going to watch a video that takes 7 minutes if they don’t know anything about it. It’s much better to start with something only a few minutes long,” Rae says. She also learned about posting times, people’s intolerance for spam, and ways to get strangers to watch by engaging with the supportive community on YouTube. “I learn something new every single day when I’m doing this, honestly. Because, just, nobody has mastered the art of it.”

She has also cribbed a few notes from the shows she wanted to emulate. “I learned how Larry David will take a simple moment, like double parking, and make a whole episode about it. So I wanted to take these small moments and create a relatable character with them who happens to be black,” Rae says.

Indeed, these small moments are the fuel that Awkward Black Girl runs on, or at least they were initially. See, for instance, J’s excruciating experience seeing a coworker in the hallway more than once in a day, which, as mentioned above, is one of Rae’s waking nightmares.


“A lot of episodes are just exaggerated versions of my own experience,” the filmmaker says. “I make the character go through experiences that I would hate to go through.”

While most of the characters spring from Rae’s pet peeves, some of them have a more specific basis in reality. The Boss Lady character, for instance, doesn’t realize she’s being racially insensitive because she peppers her statements with the word “girlfriend” in a misguided effort to appear “down.” The character is based on a 6th grade teacher who would always ask Rae questions about her hair, a trait with dimensions of awkwardness she wouldn’t understand until years later.

As much as ABG bears the imprint of one distinct personality, it has also had a lot of help along the way. When the first episodes immediately exceeded the popularity of their predecessors, Rae brought on a producer, Tracy Oliver. A pronounced improvement in production values soon followed. By the time the partners got to the fifth episode, the audience was still growing and so was the pressure to deliver quality content. Rae was stressed out trying to hold down her own office job while writing and filming the series, so she gave the go-ahead to Oliver to bring on two writers.

Shortly after, Rae quit her job in order to have more time to write. With funds running low and no guarantee of finishing out the season, Rae and Oliver decided to launch a Kickstarter campaign to keep the series going and help everyone involved make a living. They set the goal at $30,000 and eventually received nearly double that amount.

Image: Flickr user Chicagofabulousblog

The biggest help of all, though, came from one person in particular this past spring. “Pharrell [Williams] called me, and he told me how much he loves the show and who his favorite characters were,” Rae says, brightening at the memory. “He was talking about my voice and how much he thinks it’s needed. My boyfriend got home so I put the phone on mute, and I was like, ‘Do you hear all the things he’s saying on the phone right now?’”


Williams was in the midst of launching his new YouTube channel, I am OTHER, and decided that ABG should be a part of it. He was an enthusiastic supporter of the show, and he assured Rae that he didn’t want her to change anything. “Pharrell is the reason why there is a second season,” Rae says.

The second season opens up more about the life of the lead character. While the initial episodes served as kind of a catalog of awkward moments with scenes built around them, the new batch is more concerned with getting to know the people behind these moments better. There are still awkward moments, but there’s also more of J’s search for a meaningful existence.

“Web series tend to be more sketch-based and not necessarily episodic, and we’re really trying to make the second series feel like a show you’d see on TV, just in a smaller amount of time,” Rae says.

Thanks to a partnership with AMC Theaters, Awkward Black Girl is now something you can also see on the big screen. As each new episode premieres each month, Rae travels to a new city to host a screening event at a movie theater, occasionally joined by Pharrell Williams. The “eventness” of having a web series played in a movie theater has helped to legitimize Rae and her medium altogether, all while increasing the hopes of an eventual ABG TV show and film.

While Rae is currently working on packaging the show for TV, though, she also remains somewhat ambivalent about the leap from the web. “The two mediums are kind of fusing already anyway. If I could make TV money and stay on the web, I would,” she says. “If it does get on TV, though, I want to be on cable. I curse, and I say the N-word–there’s a raw element to the show that I feel could be watered down by the networks.”


The very freedom afforded to a developing voice on the Internet, though, is something that Rae is more conscious of now that she’s speaking into a megaphone for a larger audience. “The more people watch, the more I start to doubt myself and question, whereas before I would just blurt things out because I’m very impulsive,” she says. “When nobody’s listening, you can say whatever the hell you want. But when there’s a mix and everybody doesn’t know you or what your intentions are–there’s a bit more pressure to say the right thing or to be careful about what you say.”

She quickly learned the difference when more people are listening. When one of the writers on ABG made a joke that involved the word “tranny,” the LGBT community took vocal offense to it. Rae and her writers didn’t know that the T-word was fraught, but they addressed the issue and moved on. On the flipside, with increased exposure, Rae has also endured some derogatory remarks herself.

As the show settles into its second season, though, much more common is the problem of people asking Rae whether their awkward encounters with her will end up on the show. “People do worry, and some of them ask me about it. One girl in particular wanted to know if a character was based off her,” she says. “With this girl, it actually was true, but I told her no.”

One hopes the girl in question doesn’t read Rae’s interviews. That would be pretty awkward.