David B Morris

Nov 2, 2021

4 min read

Saying Bye To Issa, Molly and Everyone

Insecure Begins Its Farewell Season

I’ll miss you, okay? harpersbazaare.com

It’s always hard to express your love for a series you know you’re not anywhere near the demographic for. But I’ve had a torch for Issa, both the character and the namesake behind one of the greatest comedies in HBO’s storied history, Insecure. Because there’s no reason I should ever have liked it: it deals with the lives of thirty-ish black women in LA, often has them discussed topics I can’t began to understand and deals a lot with sex scenes that often make the ones Samantha was having on Sex and the City seem tame by comparison.

But it’s because these African-American women — and quite a few men — live and in many cases openly mock the world that people like me feel comfortable in and speak with a candor and honesty that is unmatched by few series that I have come to love this series. It’s impossible not to worship the brilliance of the incredible Issa Rae, who has a level of awkwardness in just about everything she does that makes everything that goes wrong make you love her all the more. She is constantly unlucky in everything often in spectacular ways — she may make blunders at her job by pushing for an artist who they don’t like and then won’t agree to the notes, she may throw an epic block party and then have it ruined when some one thinks they see a gun, and she will constantly get in her own way with her love life — but that just always make us love more. We root for Issa the same way we root for Molly (the incredible Yvonne Orji) who climbs the business far better than her friend, but is unlucky in love and has only just realized that the gift she has for relationships is destroying them. She’ll even sacrifice her own friendship with Issa to try and save one — as made up one of the most painful storylines in the show’s history — and then learn from that same boyfriend that she can be to hard to deal with. Is it any wonder she finds it so hard to listen to her mother try to set her up yet again?

But all good things come to an end, and Rae herself said that she always planned for the series to end after five seasons. And so the series begins in final arc with Issa and Molly going with their friends to their tenth college reunion having made so much progress and not feeling it one bit. Issa finds herself talking at a panel of entrepreneurs and is, as is her fashion, utterly incapable of saying the right thing. Molly finds herself dealing with an old college crush she can’t approach. Of course, there’s far deeper hilarity — one of their friends is listed as dead, even though she’s at the reunion with them and is royally pissed off by the eulogies that are there — and both Issa and Molly go out for dinner and find themselves being robbed by one of their old classmates. In typical fashion, they return to the car and start laughing hysterically at the experience.

It does look at the very least that Issa and Molly are finally rebuilding the friendship that was shattered last season after what seems to be a year of trying. One of the sweetest pieces of last night’s episode was Issa and Molly getting together to watch TV, Molly dozing off and Issa pulling the couch open to sleep beside her friend. And for a change Issa’s career may finally be heading in the right direction — after an event that looked like it would be a disaster, her bosses actually seemed to love the performance. Of course, romance is not looking as good for her. She still is pining after Lawrence (Jay Ellis) and just as it seemed like last year they were finally going to get their timing right, in the last minutes of the season Lawrence learns his last girlfriend was pregnant. They seemed to have been trying to go on in the interim, but it didn’t look good in season premiere and it’s really clear she’s not ready to move on.

“If you knew this was the end, how would you like to be remembered?” one of the friends says in a podcast in the fifth season premiere. It’s a totally self-aware moment, of course, but if Insecure hasn’t earned it by now, I don’t know when they will. Here’s how I’d like to remember it: one of the most brilliant comedy series of the 2010s, launching to superstardom the careers of some truly brilliant actress and a whole lot of nominations and awards from every possible group that exists. Insecure’s already managed the first two, in my book. As for the last one, let’s have the Academy have the same nagging voice in their head that Issa always does.

My score: 5 stars.