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Issa Rae: A Relatable Star in the Making  

Devoted fans gathered at the historic Sixth & I Historic Synagogue on a cold night recently to hear author — and YouTube sensation — Jo-Issa “Issa Rae” Diop discuss her new book, “The Misadventures of Awkward Black Girl .”  

Throughout the evening of Feb. 24, Issa Rae displayed her trademark wry sense of humor while touching on a range of topics including her path to stardom, portrayals of black women in media and the challenges of writing such a candid collection of personal stories. For Rae, success didn’t come overnight, nor was her path resistance-free. The 30-year-old writer’s journey — which she calls one of patience, perseverance and self-doubt — began 12 years ago in the Stanford University drama department and included stops in New York and Los Angeles.  

“At Stanford, it started there because the drama department was predominantly white, and I didn’t see where I really fit in,” she said. “Doing the [school production] ‘Hip-Hopera,’ I met a young girl who took means in her own hands and just decided to create a production and cast people of color. And then she left, so there was a void. I really enjoyed acting, but being behind the scenes directing and producing and building something from the ground up really appealed to me.”  

But after shopping around a script (which was a semifinalist at the Sundance Film Festival) in Los Angeles and being told “everything short of ‘no,’” Rae decided she was tired of asking for permission from Hollywood gatekeepers and took matters in her own hands by experimenting on a then-new website, YouTube.  

While at Stanford, she produced a YouTube series called “Dorm Diaries,” a “mockumentary” about her experiences at school there. The series caught on at universities such as Duke, Howard and Harvard. “It wasn’t lost on me that I had just written something, put it out there and had direct access to an audience that shared it,” she said.  

As Rae recounted her struggles and shared anecdotes from her past, her fans in the audience, many of them postgraduate self-professed “awkward black girls,” nodded their heads along in a visible sign of recognition. Many of the women in attendance seemed to have been long awaiting someone such as Issa Rae to speak about their experiences, one ignored by mainstream entertainment.  

“I am familiar with ‘Awkward Black Girl,’” Brittany Osazuwa said. “I do watch it at work when I’m not working, ” she continued, laughing. “I do catch it from time to time. I relate to it. It’s life, being a black woman.”  

But it isn’t just young black women who find Rae appealing.  

“I’m not as familiar as others here with her web work,” said a smiling Peter Kosmala, a 50-year-old white man living in D.C. “I saw a couple of episodes and was intrigued. And then I heard that she’d come out with a book and I definitely wanted to see her in person.” After listening to her speak, Kosmala said, “I thought she was great.”  

Rae first gained national notoriety for producing and starring in the web series, “The Misadventures of Awkward Black Girl,” which debuted on YouTube in 2011. The YouTube show mined comedic gold from the everyday awkward personal interactions revolving around work, relationships and race.  

Rae said the idea for “Awkward Black Girl” was born out of a frustration with portrayals of black women in film and on television. She felt that the characters she saw on popular shows such as “Flavor of Love” were there merely to entertain by conforming to negative stereotypes of black women. In an effort to get out her story, and those of women like her, Rae sought to create characters who were first recognizable and relatable, but also happened to be black.  

After two seasons producing the Web series, ABC hired Rae to begin working on the pilot for a show entitled “I Hate L.A. Dudes” with one of the most powerful women currently working in television, Shonda Rhimes, the producer behind runaway network smash hits such as “Scandal,” “Grey’s Anatomy” and “How to Get Away With Murder.”  

ABC ended up passing on the pilot, but it didn’t take long for her to land on her feet. HBO recently ordered the pilot for “Non-Prophet,” a show she co-created with television veteran Larry Wilmore (“The Office,” “The Nightly Show”). She also created a stir with “The Michelle Obama Diaries,” which had people debating whether she was hilarious or crossing a line.  

Rae said to prepare for writing her book, she read chart-topping memoirs such as Tina Fey’s “Bossypants ” and Mindy Kaling’s “Is Everyone Hanging Out Without Me? (And Other Concerns) .”  She also said sharing so much personal information in a book was a bit of a challenge, but the writing process ultimately proved to be therapeutic.  

“Writing this book felt like I was writing a journal entry, like I was writing in a diary,” she said. “It was just me alone with my thoughts and my experiences. So I did get to talk about my parents’ divorce and talk about my dad’s infidelity in a way that I never addressed to myself, to my friends or to my siblings.”  

After reading her manuscript, Rae said she felt a bit of trepidation for what she felt was “airing dirty laundry.” But after speaking with her father, she was encouraged to be respectful of her family, yet honest in telling her story.  

Throughout the book, she strikes a delicate balance of telling stories that target a very specific audience (“Hair Hierarchy” — a hilarious account of her struggles in embracing her natural hair style) with those containing a broader appeal (“New York, NY” — about falling in and out of love with the Big Apple). And of course there are stories that hit on more universal themes, such as her advice on navigating awkward workplace situations, “ABG Guide: When Co-workers Attack.”  

The book, which has drawn praise from the likes of Kaling and Lena Dunham, was released on Feb. 10 and made The New York Times’ best-seller list.  

“I thought it was hilarious,” Ashley Henriquez, a 24-year-old woman who describes herself as a huge fan, said of her experience at Sixth & I. “It was very personable. I felt she related to everyone in the crowd.”  

It’s perhaps Issa Rae’s honesty and relatability that inspires such devotion in fans.  

After the interview, her book-signing line nearly wound outside the door and just as the Q&A segment began, a fan ran up to the stage and threw her a pair of large white “granny” underwear before yelling, “I love you Issa Rae!”  

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