Issa Rae With her own unique flair and infectious sense of humor, Issa Rae's content has garnered over 25 million views online and a Golden Globe nomination for Best Actress for her hit show, HBO's Insecure. Issa's web series, The Misadventures of Awkward Black Girl, was the recipient of the coveted Shorty Award for Best Web Show and her first book, a collection of essays, is a New York Times Best Seller. Issa has graced the cover and pages of major national media outlets including Essence, The Hollywood Reporter, Vanity Fair, The New York Times, CNN, VOGUE, TIME, with appearances on The Tonight Show with Jimmy Fallon, Good Morning America, The View, and more.