From YouTube star to multi-hyphenated artist, Jo-Issa Rae Diop (known to many as Issa Rae) has made her mark in the entertainment industry as an actress, writer, producer, and entrepreneur. With the fifth and final season of her hit HBO show Insecure coming to an end, many of her fans are marveling over watching her grow on and off of her show.
Issa began her career in college with her web show Dorm Diaries, as she wrote and directed the show based on the lives of her friends while at Stanford University. After she graduated in 2007, she began a fellowship at The Public Theater in New York. She then decided to create The Mis-Adventures of an Awkward Black Girl, which was based on her personal life as she had difficulty meeting new people and navigating uncomfortable situations. She also wanted to create the perspective of an awkward, nerdy black girl because that was missing in the entertainment industry. The show gained popularity during its time and even won a Shorty Award for Best Web Show.
In 2013, she began writing the pilot for Insecure, which follows the life of Issa Dee as she enters her 30s and defies the “strong, confident Black woman” narrative that is mostly seen on TV and in movies. Much like The Mis-Adventures of an Awkward Black Girl, the series follows Issa through uncomfortable everyday situations. Since the show’s beginning in 2016, it became increasingly popular because of its authentic storytelling of real-life situations that the characters go through revolving around work, sex, and friendships. Aside from highlighting gentrification and areas that don’t get enough recognition in LA, Issa also wanted to put a spotlight on African American actors, writers, and producers by giving them jobs on her show. She states that it’s her, and those working with her, mission to “open the door and keep the door open to make sure that we create a pipeline.” For many people working on the show, it was their first time working in a truly diverse environment where they weren’t criticized because of their race, gender, or sexuality. She also changed the lives of many of the production crew and actors by providing them with their first experience with entertainment.
Outside of the production process, Issa began to revolutionize the TV industry by providing the world with a show that captures black life and culture in a real and positive light. The show gained popularity because it’s one of the few mainstream shows that portray black life and culture without drowning its viewers with black trauma, suffering, and stereotypes. In an interview with Issa by Entertainment Weekly, the show’s stars talked about the show’s authenticity. “It’s like, we don’t want to watch normal life — but once you get into it, you realize that’s important because we need to normalize these things because we don’t see them enough.”
While Insecure took up most of Issa’s time, she also starred in many movies including The Photograph, Little, and The Lovebirds. She has also continued to provide new opportunities for up-and-coming artists and creatives through her production company HOORAE, formerly known as Issa Rae Productions. This company is made up of her many interests in Film, TV, and other digital content. Working with HBO, HBO Max, and Warner Bros., her company has created many new shows including Sweet Life, A Black Lady Sketch Show, and Rap Sh*t, which began production this past summer. Issa also began work in the music industry with her label Raedio, which works with music supervision, publishing, and the creation of music and audio for film, tv, and brands.
Even though she’s received many award nominations, graced several magazine covers, and recently signed a nine-figure deal with WarnerMedia, she still feels uncomfortable and out of place, and that feeling, the same one that sparked The Mis-Adventures of an Awkward Black, will always be within her.