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. 

Happy Birthday, Issa Rae: Fem Film Rogue Icon Spotlight

 

On this day, a superstar was born at the right time to a Senegalese doctor father and a teacher mother, Jo-Issa Rae Diop known to the world as simply Issa Rae, a humorous actress, talented writer/producer/creator/New York Times Bestselling author, and avid supporter of Black voices. 

Rae, a Stanford grad took a huge bite of American pie, taking on the web with the terrific series The Misadventures of Awkward Black Girl. TMABG was a fresh, relatable view at the other side of Black girl life in a hilarious, vivid arena that television could not touch most likely due to its star and storytelling being unapologetically Black during a moment where such crucial stories were not always told by Black voices, let alone starred monoracial Black women. The big plus was the natural hair movement too— that a dark-skinned J had her big chop and didn’t look back. Essentially, J’s positive mirror reflections would soon migrate into award-winning television. 

Yes. Yes.

Years later, HBO granted Rae the reins to co-create Insecure, another vehicle to showcase her unique characters to a larger audience, showcasing the pitfalls of Black women who still did not have themselves completely together even after turning thirty. They did not have to have it all figured out, let alone be Black women stereotypes. Yet just like in TMABG, female friendships were essential, a glue that was either stuck together or unevenly lopsided much as seen between Issa/Molly. 

In addition to making sure that Black women were watching shows with them first in mind, Rae was producing other talented artists, ushering them into a back door ala Issa Rae Presents, a YouTube platform that features incredible short films like Inamorata and web series like First and the Emmy winning Giants. 

Nominated four times for a Primetime Emmy including for Best Comedy Series and two time (hopefully three) Golden Globe, this BET Award, four time Black Reel, NAMIC, and Satellite Award winner has made many wonderful things happen onscreen and off. On the big screen, Rae has starred in films: Little, The Hate U Give, The Photograph, and The Lovebirds. 

Coming next for Issa Rae is Vengeance, a horror/mystery thriller written by B.J. Novak and a comedy titled Empress of Serenity co-starring Bill Hader. Her Issa Rae Productions will be producing Seen & Heard, a two part documentary on the history of Black television. 

Great moments have happened due partly to Issa Rae’s growing influence— after all, she has defined a whole new vibe. Her vibrant creativity and sweet nod to Black pop culture shows love and respect to those before her while propping up those coming after her. She has inspired up and coming creators to believe in themselves, to acknowledge their respective upbringings, and share unique stories to the forefront. She is not only an innovator, she is a phenomenal leader bringing multitudes of Blackness into a gratifying, fun, hilarious future that we deserve to see. 

Some of Issa Rae’s most memorable quotes include: 

“I’m rooting for everybody Black.” 

“For a long time ... I defined myself by what I wasn’t, which constantly set me up for failure and disappointment. And, my life changed when I focused on what I was good at, what I liked most about myself and what made me stand out.”— from her 2017 Black Girls Rock speech

“It's a bit cliche, but you can't go wrong by writing what you know. Even if you're a horrible writer, your own knowledge and experience is unrivaled. Nobody knows what you know like you know what you know. The way you see things is pretty unique.”

“The black characters on TV are the sidekicks, or they're insignificant. You could put all the black sidekicks on one show, and it would be the most boring, one-dimensional show ever. Even look at the black women on 'Community' and 'Parks and Recreation' - they are the archetype of the large black women on television. Snide and sassy.”

'The Misadventures of Awkward Black Girl' Kept It Real

The Misadventures of Awkward Black Girl logo.

Nothing seems more relatable than the classic The Misadventures of Awkward Black Girl, a two-season web series of 25 must-watch episodes. J (who shares my nickname) has been one of the most iconic characters ever invented, especially for nerdy Black girls looking for quirky images of themselves. 

The first episode was an instantaneous "you get me," like when love hits a person in a full, cataclysmic force.  After a breakup from a long-time boyfriend, J cuts off her hair, her ex comes back, and doesn't see her as desirable anymore. It brushes on most men's long hair fetishes, equating hair with femininity. The Black community is further problematic. When Black women break free of relaxers and pressings, glorying in their natural hair, Black men weren't necessarily on board at first. For darker skinned women, historically seen as closest to masculinity, wearing cropped hair was foolishly viewed as a great evil. J doesn't let the ex's opinion hurt. Her short hair is a defiant statement that never changes as the series progresses along. In addition to her deep brown skin and beautiful short natural, J represents the average Black woman, our bodies, our interactions with the world around us. Such a golden, honest reflection.

J (Issa Rae) often found herself in wacky tough spots, but her TWA and earrings were always on point.

Unfortunately, J has to deal with an awful work environment. Hanna, her boss is an inappropriate culture vulture, Nina is a particularly nasty bully, Germy Patty holds snotty tissues like safety blankets, Darius's whisper voice is irritating, and lovesick A follows J around, not taking the politest of rejection hints. J finds endearing highlights in her best friend CeCe and adorable, seemingly unrequited crush on Fred, the new guy. With CeCe, J has found a great companion, a gal just as awkward as her. In fact, their hallway interactions were delightfully humorous and a spot on testament of office discomfort. 

J (Issa Rae) smiles often, even in situations that don't call for smiling.

J's other office favorite-- the kind, supportive Sir-Smiles-A-Lot, Fred, then begins a big triangle. She has much in common with anger management counselor White Jay, whom she met at Fred's birthday party. Fred realizes much too late that he likes her. She ultimately has to decide between the two, leading to a sweetly surprising season one finale. If including A and the lesbian receptionist in the whirligig of J's love life, J was quite the catch. 

The Misadventures of Awkward Black Girl dishes out a fully thought out curriculum in a smart, refreshing way. It daringly brings up all the things we ever thought about, going over: proper car behavior (if it's someone you don't like or regrettably slept with), dance party etiquette, dating, job interviews, boyfriend's terrible friends, and all those finicky situations in between. Yet displayed through the eyes of a girl that looks so much like us. She doesn't have it quite together. And that is okay. Her rap flows are legendary and her killer internal dialogue is the stuff laughter is made of. 

J (Issa Rae) is every young woman whoever feels out of place-- whether it be at a public function or where we are in our lives (financially, emotionally, physically).

While network TV has room to catch up to Black women in leadership roles and cable is slowly becoming a space, the web series remains the most solid place to find us. The Misadventures of Awkward Black Girl inspired a longing for other great Black women characters in this short digital format. American Koko's Agent Koko, Sam Bailey's You're So Talented, and Hermione and the Quarter Life Crisis's Black Hermione showcase Black women in all faucets of individuality. 

Issa Rae has taken over HBO with award-winning Insecure and is currently in Little (which reunited Rae and Tracy Y. Oliver-- The Misadventures of Awkward Black Girl's Nina and the web series producer/writer). Up next, Rae stars in The Lovebirds with Kumail Nanjiani and Stella Meghie's The Photograph. Insecure's fourth season has been pushed to 2020.

Issa, the bonafide star on the left. The Misadventures of Black Girl cast: Fred (Madison Shockley III), Jesus (Michael Ruesga), J (Issa Rae), White Jay (Lyman Johnson), Jerry the Temp (Ricky Woznichak), CeCe (Sujata Day), and Denise (Devin Danielle Walker).

Every time the desire to binge The Misadventures of Awkward Black Girl comes on, the temptation cannot be denied. Stories are funnier, wittier. Above all, the world of J will never stop resonating.

The First Time I Saw Myself Onscreen

Adepero Oduye in Pariah.

My single mother wasn't the affectionate and maternal sort like Clair Huxtable, let alone affluent and married. So the television raised me on exclusive beauty, slowly and subliminally forcing me to admire fictional characters that looked nothing like me. I grew up watching an endless amount with a preference for soap operas and addressed that in prelude to last year's series on Best TV Couples here. I didn't go to the cinema until around age seventeen, but always had a Halle Berry haircut (though my hair didn't like perms at all, lasting for a week or two before unapologetic nappiness returned). Every boy in school desired Halle Berry. Unfortunately, I (and most of the other Black girls) didn't resemble her at all.

On Saturday mornings, Lisa Turtle (Lark Voorhies) taught me about funky style and fashion on white centric Saved by the Bell.

Her outrageously fabulous wardrobe and dreams for fashion school truly resonated with me. 

When last summer Ava Duvernay asked the question, "when did you first see yourself depicted on screen?" I simmered on the thought for a while, remembering the biracial and non-black women still heralded, still put on higher pedestals in all forms of media. I do recall childhood animated icons: Punky Brewster's Cherie, Jem and the Holograms' Shana Holsford, and The Magic Schoolbus's Keesha Franklin (the later two having been recently turned into racially ambiguous characters). Yet I couldn't hold onto them forever.

Although I didn't watch Felicity, it was special seeing Tangi Miller in those memorable "Oh What A Night" WB commercials. She would the only Black woman, essentially playing the role of spokesperson for our notably absent presence on the network. 

The teenager years were absent of Black girls. I escaped into the WB network (didn't have cable) and eating disorders, wishing to banish the newfound curves alongside my "problematic" short hair and distinctive face that looked like countless masks in the Africa sections of museums than anything on TV or film. It felt entirely wrong to be dark skinned with a broad nose, plump cheekbones, thick lips, and size 0 fantasies. Yet Tangi Miller's sepia skin, dark brown eyes, and long box braids in the commercials between consumptions of Buffy the Vampire Slayer, Angel, and Roswell soothed a great inner belonging. She was in the Seventeen and Teen Vogue magazines, but never graced the covers. Always the support, the sistah girlfriend to Keri Russell's lead, Miller lingered in my mind, my spirit, constantly reminding me that we deserve to fit somewhere. Funnily enough, at the time, she was also dating Angel's J. August Richards. I imagined them as the Black King and Queen of the WB, that they clung to each other on a network lacking the very definition of inclusivity.

Adepero Oduye in Pariah.

Thus, the first time I saw myself depicted on screen was poignantly nestled in Adepero Oduye's performance in Pariah as Alike, the shy writer coming to terms with her sexual identity. I remembered racing down to the Neon Movies-- the only art house theater in Dayton, Ohio-- to watch a film that many heralded online, knowing full well that Black films, especially Black films with strong leads directed by women (Night Comes On and Fast Color) tend not to stay in theatres long.

Oduye's character not only looked similar to my physical (skin tone, prominent African features), she didn't wear makeup, loved English, wrote poetry, rode public transportation, and was constantly ridiculed by her peers for not appearing feminine enough. I sought solidarity in Alike hiding her true self, admiring the authenticity shining through Oduye's performance. She began my search for other similar multifaceted characters, for finding those that don't fit the European gaze, their expectation of Blackness, whilst also looking for validation in gifts they could offer the world.

In addition to Oduye, Whoopi Goldberg and Akosua Busia in The Color Purple, Alva Rogers in Daughters of the Dust, Mouna Traore in Brown Girl Begins, Karidja Toure in Girlhood, Samantha Mugatsia and Sheila Munyiva in Rafiki, Dominique Fishback and Tatum Marilyn Hall in Night Comes On, and Marsai Martin in Little all come to mind as to how I see myself portrayed in both past adolescence and current adulthood on the film screen.

Awkward Black Girl, one of the best web series' ever, conveyed my experiences in the workplace. Plus, Issa Rae's expressions are on point.

Whether it's having a deep dark brown skin complexion like Issa Rae or Lupita Nyong'o, an impressionable gap between teeth like Uzo or distinctive negroid facial features and kinky hair like Viola Davis and Danai Gurira, finding these parts on another person in Hollywood has become a new source of unexpected joy. The representation of Black beauty-- the unapologetic, unambiguous African ancestral pride-- is taking phenomenal shape and putting us all on notice in a big, unforgettable way.