Goodbye Issa, Molly, & Co., An ‘Insecure’ Final Season Replay, 2015-2021

Molly (Yvonne Orji) and Issa (Issa Rae) are back to bosom buddy status in Insecure’s season five opener— Reunited, Okay? directed by Melina Matsoukas and written by Amy Aniobi. 

“You’re always gonna be in my loop.”—Issa Dee to Molly Carter [insert hearts for eyes emoji here]

On October 9, 2016, a brilliant show debuting two days after my birthday, cordially introduced us to two Black women of similar complexion in leading roles defining change from the typical dark skinned versus the lighter skinned setup— toxic colorism often seeping into the characterization. Part comedy and part drama, Insecure on HBO brought attention to specific problems young Black women faced— tokenism/undermining at the workplace, neighborhood gentrification, lack of communication in romantic relationships, questioning self-worth/value, and that specific kind of love reserved for our girlfriends. With the backdrop of Los Angeles starring as another character including The Dunes in Inglewood, the struggles of Issa and her friends were relatable, honest, and refreshing. 

College Issa (Issa Rae) and Molly (Yvonne Orji) shown at Tiff and Derek’s going away party.  

The fifth and final season begins with the gang heading to their old college stomping grounds— Stanford University. After a rift that slowly ruptured mid-season three all the way to cracking into smithereens in the previous fourth season, Issa and Molly are trying to repair the damage. Why not restart at the very place they met? Although Molly asks Kelli for advice on how to begin anew, it shows growth that Molly decides to present this question to Issa herself. 

“Are we going to be okay?”

Thankfully, it is a resounding “yes.” 

Before Issa (Issa Rae) and Molly (Yvonne Orji) sleep, Molly starts singing the corny “You’re My Best Friend” song— very sweet throwback nod. Unfortunately, Issa tells Molly it’s wrong in episode two’s Growth, Okay?! directed by Mo Marable and written by Phil Augusta Jackson. 

Growth, Okay?!, the second episode, contains super special moments only true BFFs could share— cooking together or ordering out, sleepovers where a friend will give you a pillow because you’ve fluffed hers out, movie nights, phone calls— all the cozy stuff. Plus, Molly is rocking a gorgeous natural cut— which reminds one of first season Issa’s fresh TWA. 

The girls— Kelli (Natasha Rothwell), Molly (Yvonne Orji), and Issa (Issa Rae)— looking good for the beach in Faulty, Okay?! directed by Mo Marable and written by Syreeta Singleton.  

The overall key highlights were the growth and trust Issa and Molly were able to achieve. By the end, their conversations were coming from healthy angles. None of the judgment or shame or side eying took usual steed. They safely asked each other questions on relationships and career choices— taking the time to listen and offer critical feedback from a much friendlier angle. The incredible loyalty that they show has definitely become one of the most compelling “ride or die” stories ever told. 

The girls hug it out during a round of games, joints, munchie snacks, and wine (nonalcoholic for Kelli) in episode seven’s Chilling, Okay?! directed by Amy Aniobi and written by Fran Ritcher. They did not eat any real food this episode. 

The Denver move is sad yet believable part of life. Friends actually move away— create roots in another city, another state. When Tiff announced the news during the seventh episode Chilling, Okay?!, a certain reality started to sink in. This foursome would be losing a key person, a person still recovering from a vulnerable year. Tiff— already somewhat private about her emotional/mental health and never completely sharing what happened between her and Derek— isolated with only Derek and Simone is both heartbreaking and bittersweet. Kelli, Issa, and Molly will no longer access Tiff in their traditional way, but that bond with Tiff will not be completely severed. Maybe Denver represents a new perspective for Tiff. 

Overall, this was such a delightful joy! Molly not ever watching Love Jones— a hot mess. The throwback John Legend and Alicia Keys— what a time! The A Different World setup as the girls changed clothes. Kelli’s outbursts. Baked cookies with Doritos? And of course the Daniel King / Daniel Kaluuya love. 

Molly (Yvonne Orji) gets slapped by Kelli (Natasha) for not sharing an edible with her friends at Tiff’s swanky going away party in season five, episode nine’s Out, Okay?! written, directed, and cameo’ed by Prentice Penny. 

The last episode was all about crying, crying again, and crying some more. Whether a big surprise, an intimate dinner, or travel to Mile High City, Issa, Molly, Kelli, and Tiffany keep the promise to celebrate their birthdays together. From Los Angeles to Denver, in the face of change, the girls are determined to hold on tightly to their extremely close friendship. Meanwhile tragedy strikes in between. Molly losing her mother hit home for me personally having lost my beautiful single parent last summer. My brother was also the caller of bad news. Thus, when Molly broke down and cried, I cried along with her— a day after Christmas, sobbing at the reality of such a significant loss. No one can ever be truly prepared for that kind of grief. 

Also Molly’s wedding day— marrying Taurean, the father/daughter dance, Molly’s coworkers as bridesmaids (the very ones she tried upstaging long ago) alongside her best friends, and Issa and Molly’s tender gown scene—tears for eyes at that point. Out of all the characters, Molly has the most genuine maturation. She has easily come from being number 10 on the Top Insecure Characters to somewhere in the Top 3. Her progress shows that inner reflection, diligent patience, and understanding will pay off in a good, positive way. 

And Issa.

Wow.

Our girl went from being a disrespected token at her disingenuous workplace (that unfortunately still exists) to becoming her own boss and having the very best intern/assistant in Quiona. Issa always knew that she wanted to give to the community. Always. That mentality, that drive was in there— waiting. Once she faced tough challenges head on, she could no longer be stopped. In an imagined future, we can see a few We Got Y’all kids coming to The BLOC events, happy to see Miss Issa not only thriving for herself, but also for them and their community. 

Birthday girl Issa (Issa Rae) shares a laugh with her now married BFF— bringing it full circle right down to the Broken Pussy song in the Insecure finale— Everything Gonna Be, Okay?! directed by Prentice Penny and written by Issa Rae. 

Although on December 26, 2021 the last ever Insecure episode aired right after Christmas Day, like The Misadventures of Awkward Black Girl, it will not ever be forgotten. Thank you, Issa Rae, Prentice Penny, and the rest of the excellent cast and crew for being a crucial part of so many lives for five seasons. Your generosity, talent, and direction has been commendable— has been cemented in our culture. We will always look back on this inspiring, award-winning/award-robbed show with great fondness, especially for the laughter, the music, the art, the fashion, and the hairstyles. 

At last, with Insecure our scene is seen.