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Review: Issa Rae's 'Insecure' Returns to HBO With a Third Season Focused on Your Work Self, Your Real Self, and the Messiness of Both

By Roxana Hadadi | TV | August 13, 2018 |

By Roxana Hadadi | TV | August 13, 2018 |

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“Life’s a bitch and then you die,” go the lyrics of Radiant Children’s “Life’s a Bitch,” used on the closing credits of last night’s Insecure season three premiere. Is that more fatalistic than we’re used to on Issa Rae’s groundbreaking half-hour HBO comedy? Sort of, but “Better-Like” is the introduction of a season focused on that itch to prove yourself, professionally and personally, which becomes more persistent the longer you stay in the same place, stuck in the same rhythms.

If you never change, then yeah, life is is a bitch and then you die. And sometimes even if you change, those transformations don’t go down exactly as you hoped or envisioned. Life is getting up every day and doing the damn thing over and over again, and that’s where we are with “Better-Like,” which takes place a few weeks after the events of the season two finale “Hella Perspective.” In that episode, which cycled through the perspectives of Issa (Rae), her best friend Molly (Yvonne Orji), and her ex-boyfriend Lawrence (Jay Ellis), we saw each character make significant moves: Molly realized that her law firm would never appreciate her talent, Issa moved out of the apartment she used to share with Lawrence before she cheated on him with old flame Daniel (Y’lan Noel), leading to their breakup, and Lawrence’s new relationship with a coworker fell apart.

In “Better-Like,” Lawrence is nowhere to be found, but Issa and Molly are each tackling something new, and the show handles these developments with its characteristically excellent writing, electric chemistry between Rae and Orji, and strong sense of self and place. On top of her full-time job at the nonprofit We Got Y’all, where she remains removed from field work, Issa has also started driving for Lyft. Offering her riders Capri-Sun pouches and candy (were those gummy bears? PARTY LYFT!), Issa uses Lyft not only for extra cash but also to escape the sounds of Daniel having vigorous sex with Vanessa (Candice Ramirez), who Daniel’s sister, whom we meet along with his niece, calls “old girl.” While Issa is hustling, Molly is relaxing, going on vacation by herself and returning to a new job, having finally left her old law firm after spending most of season two trying to prove herself to the white male higher-ups. During a diner meal that is one of the best examples of friendship I have ever seen on TV (so much heat between Issa and Molly over that broken vase!), Molly pledges her new approach to “know better, do better,” but soon she’s on the receiving end of some vigorous oral from Dro (Sarunas J. Jackson), the married man she can’t seem to quit.

Old habits die hard; later in the season (I’ve seen “Better-Like” and the next three episodes, “Familiar-Like,” “Backwards-Like,” and “Fresh-Like,” but I’ll try to avoid spoilers here), characters say things like “Too old for this shit” and “It’s hard to start over,” which sound like clichés but in the context of Insecure, which is so interested in how and why people make the choices they do, make perfect sense. When you’re in your 30s, certain behaviors may no longer be healthy, but they’re all you know: chasing after professional opportunities after a string of failures, hooking up with the same people, indulging in the same petty arguments and disagreements with people who were once your friends. Your 20s are supposed to be messy, but your 30s? Aren’t you supposed to have it together by then? Shouldn’t your credit score be better? Shouldn’t you have settled down with a romantic partner? Shouldn’t you feel fulfilled in your job? If you only have one of those things — or none of them — what do you even have to be proud of?

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The “older and wiser” assumption is one that Insecure disproves with each episode, while at the same arguing for the benefits of incremental, consistent progress. Daniel and Issa have history, so his parting declaration of her as “roommate” is certainly a dig, but Issa needed someone to finally call her on her bullshit — to force her to admit that Daniel is one of the only consistent people in her life, and more important to her than a hook-up. Dro’s wife may be OK with his relationship with Molly, but how ugly he turned when she asked for her key back is a sign of possessiveness that Molly needed to see — is Dro really worth all that self-doubt? And that’s just the romantic stuff; whether Molly can stand to stay at We Got Y’all now that she’s stuck doing paperwork all day and seeing the shortcomings of the organization, or how Molly will approach her new job after only having experience at one other place, are question marks, too.

But that’s adulthood, right? Attempting to make the right choice, doing all the “right” things to get there, and realizing that nothing is guaranteed, that you can’t control other people’s reactions or opinions, that you can only take hold of yourself. Look at how often Issa thanks Daniel this episode, attempting to put in words how he makes her feel, or how many times Molly acts in ways that are contradictory, doubling back on promises to herself because the temptation to self sabotage is too strong. Think about how Dro says to Molly after the fight in the Lyft involving rider Nathan “with the face!” (Kendrick Simpson) that “You and Issa do the fucking most,” and of the pair of young women that Molly and Issa picked up who reminded them so much of their prior selves. Molly and Issa aren’t those girls anymore, but they’re not the people they want to be quite yet, either. That space in between is what Insecure is so good at exploring, and season three is stronger than ever.

Other odds and ends:

+ The show within a show this year is Kev’Yn, a reboot of a fictional black sitcom that features the familiar faces Erika Alexander (Living Single!), Bill Bellamy (was I the only person who watched Fastlane?!), and Darryl M. Bell (A Different World!).

+ How much Issa reps for Los Angeles is a consistent theme throughout the first half of season three, and I appreciated that both Issa and Frieda (Lisa Joyce) wear shirts from LA Iranian-American fashion designer Melody Ehsani, whose boutique is a must-shop destination for locals.

+ The music this season continues to be excellent; here’s the Spotify playlist.


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Roxana Hadadi is a Senior Editor for Pajiba. You can follow her on Twitter.

Image sources (in order of posting): HBO Twitter, Insecure Twitter