How Issa Rae Built the World of <em>Insecure</em>

Sitting in a New York City hotel room with a plastic flute full of prosecco and strappy black Manolo Blahnik heels resting near her bare feet, Issa Rae looks like the kind of woman who would have petrified an earlier avatar of herself. If you remember J, the endearingly cringe-inducing protagonist of Rae’s early-2010s YouTube series, The Misadventures of Awkward Black Girl, then you know she was a far cry from the woman who now has her face on magazine covers, billboards across the country, and the festive blue cake sitting on the table in her hotel suite.

Today’s Issa Rae is also a long way from Issa Dee, the cloddish Millennial at the heart of the acclaimed HBO dramedy Insecure, which will end its fifth and final season on Sunday. For much of the series, which draws on Rae’s own travails in her late 20s and 30s, Issa Dee has been, in the simplest of terms, a mess. She has stumbled through infidelity, the protracted demise of a long-term relationship, several more unfortunate romantic entanglements, and a series of unglamorous jobs. Issa Dee certainly doesn’t wear Manolos: In the first episode of Season 5, a thief deems her shoes too tacky to steal.

’s popularity has always been powered by its candid explorations of career-related ennui, the difficulties of maintaining old friendships into adulthood, and the allure of trying on a new life. The series has been devoted to showing how these everyday trials are experienced by Black characters, even if those characters are sometimes trying to navigate predominantly white corners of the professional world. In the years before and debuted in 2016, viewers were unaccustomed to seeing the mundanities of Black life depicted on television; with some notable exceptions, many Black people on TV at the time were either minor characters on white-led series or reality-TV personalities. By filling that void, became a Black, coined in the show’s pilot, even inspired .