9 unforgettable moments of Insecure Season 5

For five years, Issa Rae’s HBO show Insecure has captivated viewers with one of the most authentic and complex portrayals of the Black female experience on TV today.

Co-created by Rae and Larry Wilmore, Insecure was born of Rae’s popular YouTube series The Misadventures of An Awkward Black Girl and follows best friends Issa Dee (Rae) and Molly (Yvonne Orji), and their other friends Kelli (Natasha Rothwell) and Tiffany (Amanda Seales), as they stumble through life and adulthood.

And it has always been relatable, whether it’s dealing with Issa and Molly’s messy dating lives, their friendship, which has defined some of the show’s most memorable moments, or their very different professional lives.

Away from Issa and co’s dramatic lives, Insecure has also showcased Black culture – from Issa wearing bold T-shirts that make a political statement or pay homage to music icons like Nina Simone and Prince, to displaying murals and art by local Black artists from Issa’s Inglewood neighbourhood to featuring great soundtracks by both established acts like Kendrick Lamar and SZA and lesser-known, emerging R&B and hip-hop acts.

During the course of its five-year run, Insecure has racked up 11 Emmy nominations, including Outstanding Comedy Series in 2020 and Outstanding Lead Actress (for Rae) in 2018 and 2020, three Golden Globe nominations and four Critics’ Choice Awards nominations.

The show has also remained fresh for all five seasons with a score of 97% on Rotten Tomatoes, and in a fitting send-off for a historic show, the fifth and final season currently has a 100% critics’ rating.

But even great things have to come to an end at some point, and for Insecure, it’s truly a bittersweet moment as we bid farewell to a show that has become a cultural phenomenon and one that has left a mark on television history.

With all five seasons now streaming on Showmax, here are nine moments from Season 5 that we can’t get over.

Spoiler alert! If you haven’t watched Season 5 of Insecure yet, stop reading here, and come back when you’re done.

Kelli “dies”

While Issa, Molly, Tiffany and Kelli are attending their 10-year college reunion at Stanford, Kelli learns that her name has been included among the “deceased” to be celebrated with an In Memoriam video – a hilarious mistake that prompts her on a journey of self-discovery throughout the season.

Here’s a fun fact: Rae graduated from Stanford IRL.

Issa and Molly are friends again

Romantic relationships be damned, Insecure has always been stronger when it’s focusing on Issa and Molly’s friendship. Their bond is tested in Season 4 when everything they’ve held back for years comes spilling to the surface, causing them to drift apart as they grapple with their own growth.

So, to see them warm up to each other in episode 1 of Season 5 is a satisfying way to kick off the final season. Yes, it’s awkward at first but they finally get there – after an unexpected robbery from an old college friend that leaves Molly without shoes and Issa wondering why her shoes are not worth stealing. Just the ice-breaker they needed.

Issa breaks up with Lawrence

In the Season 4 finale, Lawrence (Jay Ellis) dropped the bombshell on Issa that his ex-girlfriend Condola (Christina Elmore) aka Condolences or Condominium (Twitter is ungovernable) was pregnant. Issa breaks up with Lawrence at the end of episode 1 because thriving-and-growing-Issa has worked too hard to be pulled into some baby mama drama.

Issa kicks Condola into the trash

In perhaps this season’s most hilarious moment, Issa confronts Lawrence and Condola and gets her revenge by kicking Condola into the trash right after tossing baby Jah across the hall. It turns out that Issa is just daydreaming but we already knew that – otherwise we wouldn’t laugh at Issa throwing Lawrence’s baby, now would we?

Molly and Taurean get ridiculously high on edibles at Tiffany’s party

Molly and Taurean (Leonard Robinson) are definitely a couple we never saw coming, seeing as he’s always been her nemesis at work. But here they are at Tiffany’s party, being all loving and caring, eating edibles together and getting high, having the munchies and raiding the buffet table for some mac and cheese balls. If that’s not love, we don’t know what is.

Kelli finds love

Armed with deadpan humour and quotable one-liners, Natasha Rothwell’s Kelli has delivered much-needed comic relief throughout the entire five seasons, earning a special place in the hearts of fans as the only character deserving of her own spin-off.

In Season 5, Kelli is still the gift that keeps giving, serving one iconic one-liner after the other, but this time she gets an arc worthy of her character (sort of). After quitting drinking to work on herself, Kelli, who never keeps any man around for too long, finally finds love and becomes pregnant!

Issa and Lawrence get back together

Issa and Lawrence’s on-and-off relationship finally gets a resolution when Issa chooses Lawrence over Nathan (Kendrick Sampson). They’ve had their ups and downs and have gone through one of the messiest breakups on the show but we always knew that inevitably, it would always come back to this moment. #TeamLawrence must be grinning.

Molly and Tauren tie the knot

Molly finally gets her happy ending by marrying Taurean. While all characters have grown so much in Insecure’s last moments, anyone who’s followed Molly’s journey – from her insanely high standards to overthinking everything – will agree that her growth is by far the show’s biggest win.

Issa and Molly share an emotional bathroom moment after the wedding

While getting Molly out of her wedding dress, Issa and Molly share a beautiful moment that had fans weeping. “Thank you for everything, Issa, just for being you and for loving me while I was me. And girl, I don’t know where life is gonna take us, but I just know that as long as you’re around, Imma be okay.”

We’re not crying, you are.

Forget Lawrence and that scene of him playing house with Issa and a now-grown baby Jah, the ultimate love story on Insecure has always been between Issa and Molly.

Relive every moment: binge Insecure S1-5 and the behind-the-scenes documentary, Insecure: The End, on Showmax.