The 2010s were a good decade for creators of web comedies to level up to TV. Some have been straightforward translations, like the stoner buddy comedy of Broad City or the extremely Canadian content of Letterkenny. Insecure co-creator and star Issa Rae, meanwhile, took some elements of her popular web show The Misadventures of Awkward Black Girl with her when she made the leap to premium cable, even though she was playing a (somewhat) new character. Over the course of five seasons of incisive comedy and character study, Rae’s Issa Dee struggled to figure out relationships of various kinds as she exited her late twenties and had to accept the burdens of unequivocal adulthood. Would she end up with on-again, off-again boyfriend Lawrence (Jay Ellis), or one of the many charismatic men who wander into her life? Would she ever feel comfortable as a Black woman in a well-meaning but patronizing white-run nonprofit that helps children of color? Would she and best friend Molly (Yvonne Orji) be able to prioritize each other with so much drama in their lives? And most important, would Issa ever make peace with the face in the mirror that questioned every choice she made? By the end, both Insecure and Issa had all the answers we wanted from them.