WIRED Pilot Program: Insecure

Issa Rae’s series is a smart, empathetic comedy about the self-doubt of being in your late 20s that engages with race without being defined by it.
InsecureIssaRae.jpeg
John P. Fleenor/HBO

Each fall, most of the broadcast and cable networks debut a ton of new shows in the span of a few months, making it difficult to sort out which ones to make time for and which to skip. So we’re starting the WIRED Pilot Program, where we highlight what you should continue watching, and what you can just let sit on your DVR until it automatically deletes. Today's entry: Insecure

The Show: Insecure (Sundays, HBO)

The Premise: Issa (Issa Rae) is 29, and afraid of settling: for her job at We Got Y’all, a south LA nonprofit staffed by clueless white idealists, for her boyfriend Lawrence (Jay Ellis), pondering his app’s business plan from the couch, for a life that isn't quite what she imagined. At the end of her 20s, self-described “aggressively passive” Issa and her driven best friend Molly (Yvonne Orji) are insecure about their life choices—and whether they’ve chosen at all.

The Pilot Program Take: As fans of her web series, Awkward Black Girl, have seen, Issa Rae knows how to make heartfelt humor about feeling uncertain. Rae brings that self-aware confusion—and rapping—to HBO’s Insecure, which she developed with former Nightly Show host Larry Wilmore.

And Rae delivers. In the pilot, Issa concisely explains herself to a classroom of skeptical kids—and to an equally skeptical bar at a rap open mic night—but it’ll take her a season to articulate who she is to herself. As she tries to figure out whether she’s landed in a life she doesn’t want, Issa is self-deprecating and indecisive, but she’s also witty and sharp. Her off-handed cleverness is especially great played against her out-of-touch boss, whose black cultural references are W.E.B. Du Bois and Booker T. Washington, and her overeager, idealistic coworkers. (When one coworker asks her why some of the black kids aren’t swimming on a field trip to an LA beach, Issa responds with a straight face: "Slavery.")

But Issa isn’t the only fully-formed character: The show works so well because her supporting cast is nuanced and unsure, too. Molly, an associate at a law firm who is asked to advise a new hire on toning down the way she talks, is both frustrated and unapologetic about her high standards; Lawrence starts out floundering and unambitious, but develops into an earnest guy just as confused by where he's landed as Issa. Even Frieda (Lisa Joyce), Issa’s painfully politically correct coworker, gets over herself enough to become an actual friend.

The Verdict: Insecure is a smart, empathetic comedy about the self-doubt of being in your late 20s that engages with race without being defined by it. (Much like Atlanta.) It’s funny and self-aware and raunchy, while still earnest.

TL;DR: If you’re ready for the uncertainty of 29, watch it.

https://www.youtube.com/watch?v=MubTJyWukp8