Issa Rae: Issa Rae. Producer: Insecure. Jo-Issa Rae Diop, credited professionally as Issa Rae, is an American actress, writer, producer, and comedian. Rae first garnered attention for her work on the YouTube web series Awkward Black Girl. Since 2011, Rae has continued to develop her YouTube channel, which features various short films, web series, and other content created by black people.