Insecure Intermissions: We May Be Saying Our Final Goodbyes, but ‘Everything’s Gonna Be, Okay?!’

Every Monday of the fifth and final season of HBO’s cultural flashpoint show, Insecure, Very Smart Brothas Senior Editor Panama Jackson and Contributing Freelance Writer Shanelle Genai have broken down the latest episode. But just like the fan-favorite show, all good things must come to an end. Since Panama recently said his goodbyes, Staff Sports and Culture Writer Jay Connor will be joining in to help close out the season, okay?! Spoilers ahead.

Shanelle Genai: Aaaaand, we’re back at it again with the last and absolutely final Insecure series recap. As you all know, the series finale aired the day after Christmas and due to the holiday being observed on Monday this year, this is coming a day later than usual. But, as MLK once said: “a recap delayed is not a recap denied.” (OK, so maybe that’s not really how it goes, but y’all get my point.) Speaking of influential Black figures with highly quotable quotes, though, let’s dive right into Issa Rae, Insecure and how things wrapped up for our fave four friend group.

I suppose I should start by saying congratulations to all members of the #LawrenceHive, as we saw Issa and Lawrence finally make their way back to each other, get married, and embark on their redefined relationship (thanks largely to the presence of Baby Jah and the absence of Mirror Bitch). Molly finally made her momma (RIP, Mrs. Carter) proud and married Mr. Morehouse himself, Taurean—at a fly ass wedding; Kelli found love and we also found out she was with child (imagine all the baby preguntas); and Tiffany and Derek are also expecting baby number 2 out in Denver. As we’ve said before many times, I wasn’t sure how Insecure would wrap things up at the pace they were going, but this ending was satisfying, despite how rushed it felt at times. Jay, how did you feel about the finale?

Jay Connor: Y’all really thought Team Lawrence was about to choke in the finals with a championship on the line?! Of course, we took home the Larry O’Brien trophy. That’s just what champions do. I wasn’t particularly fond of the fact that boring-ass Nathan let Issa off the hook by finally lining up his beard making the decision to remove himself from the situation, but within the context of their relationship and his saloon showdown with Lawrence, that actually made complete sense—even if it made for an anticlimactic, easy out. But as for the season itself, I’m glad Molly knocked her redemption arc out the park (she finally found true love and repaired her relationship with Issa), Kelli resurrected from the dead in order to flourish on her own (shout out to my homeboy James Bland for holding it down as Desmond), and Lawrence put a ring on it (blink and you’ll miss it).

I would’ve loved to see Issa chose herself and forge her own path forward without Nathan, Best Buy’s former employee of the month, or Daniel, but could this series really end any other way? There would’ve been blood in the streets.

Shanelle Genai: Ha! I, too, was Team Issa Choose Yourself but the longer I thought about it, the more it actually made sense for Issa to choose Lawrence in the end. As Jay Ellis eloquently put it on IG—it was always Issa. And it was always Lawrence. Despite the grand detours they both took before their paths led them back to each other, there was absolutely no denying that they loved loved each other. And as the cliché goes, love always wins. I won’t sit up here and act like I just wanted them to ride off into the sunset together, though; I was Team Daniel, mostly. (Yup, I said it. I stand by it and I’mma stick beside him.)

But I wasn’t as mad as I thought I was going to be with the outcome. You mentioned Best Buy earlier and I think that’s a great way to highlight one of my absolute favorite moments in the finale: Issa’s drive home. There were so many cute callbacks to previous seasons: Thug Yoda at The Dunes, The guy with the Best Buy uniform, the Rite-Aid store. I cried earlier in the ep when Molly and Issa had their heart-to-heart after the wedding but that drive home made me mad emotional too.

Jay Connor: For sure. For the most part, I’d be lying if I didn’t say the season as a whole felt uneven, but they absolutely stuck the landing and made the price of five seasons of admission well worth it. Would I have liked it if Desmond got a bit more of a build-up prior to the finale? Yes. Did we really need to see Jah helping Lawrence make a birthday cake for Issa? Nope. In a perfect world, it would’ve ended with Lawrence and Issa kissing in her office with a complimentary side of Molly’s wedding. But I also need to take a moment to shoutout Insecure head writer, executive producer, and otherwise hilarious ass nigga—as well as my homie—Amy Aniobi. She’s held this show down since day one and deserves every last one of her flowers. She’s the first person I hit up to congratulate after the episode ended. But I gotta ask: Should HBO follow 50 Cent’s lead and kick off the Insecure Cinematic Universe with a spinoff?

Shanelle Genai: Yes! Shoutout to Amy and all the phenomenal crew. There is quite literally no show without them so I’m adding in some additional flowers too, Coming to America style. But as far as a spinoff goes: as much as I would like for them to, I think they should leave it where it’s at. There’s no doubt that any of the characters would make for a good spinoff content, regardless of how many seasons it may last. But I think we’ve seen all we should when it comes to the lives of Issa, Molly, Tiffany and Kelli. I’d like to see what other amazing goodness Issa and her creative teams have up their sleeves—though I admittedly also would’ve loved to see them dive into Ahmal and Kelli’s disdain for each other because their digs were some of the best moments of the series, as were Chad’s one liners. Damn, I’m gonna miss them. What do you think about spinoffs? You up for Insecure-ish? Or Insecure Book II?

Jay Connor: Nope, but I’m here for Thug Yoda: The Animated Series. We can never have enough Black superheroes, and who doesn’t wanna see Issa’s favorite neighbor flying the friendly skies while dodging the letter “C” like a COVID variant? “You bute and you thick. What’s your name?” was Shakespearean poetry.

Shanelle Genai: That would be bool. Very, very bool, indeed. Well, seeing as how Issa was able to fast forward to the part of her life when everything turned out okay, I suppose this is where we do the same to our fave four friend group. And to you, our consistent readers, in hopes that despite whatever comes next for us all in 2022, everything will be OK, Okay?! Let’s do this again some time. See y’all in the new year!