Top Ten ‘Insecure’ Characters

How did the girls (Natasha Rothwell’s Kelli, Yvonne Orji’s Molly, and Issa Rae’s Issa) rank in the femfilmrogues top 10 Insecure characters?

Today is the big day. 

The fifth and final season of one of the best shows on television ends its run— the award-winning, highly melanated Insecure on HBO. We have seen pretty major events— cheating with crushes, various breakups, steamy hookups, ups and downs of career ambitions, and blow out public fights between besties. 

After four beautiful years learning about the Black side of Los Angeles from the mostly Inglewood based perspective, this is a personal list on the irresistible characters worth cherishing. Although some came for a season or two, they delivered a memorable impact that must be noted here. 

Molly (Yvonne Orji) has some redeeming qualities. 

10. Molly is a kick butt lawyer who always fumble relationship bags— Jared, Lionel, Andrew, and even two men from the premiere The League dating pool. From season one to season three, however, in her most imperative relationship, Molly was there for Issa through a tough breakup, donating money and time to We Got Y’all functions, hosting a special Moroccan dinner (season two’s Hella Perspective highlight), birthday hangout at The Last Dragon screening, and of course self care Sunday’s. She could always plan a top notch event. Yet she could come off catty and mean spirited, made assumptions, prioritized herself over others, held grudges, had that whole nasty situationship with Dro, and did not apologize first. 

Sometimes Derek (Wade Allain-Marcus) makes his minutes on screen quite memorable.

9.  Derek is a quiet, humble, successful husband to Tiffany. The love demonstrated in the season four finale really showcased that he was beyond the rich apple to his wife’s eye. He truly cared about her emotional and mental health, going well above and beyond to find her which differed from the pathetic police actions in the show within a show Looking For Latoya. Derek can also give good solid advice, especially to Lawrence who needs an active male listener and active feedback giver in his messy life. Still, while Derek calls out the BS how he sees fit, the words he said about being a girl dad as his daughter laid sleeping were disturbing on many levels. 

Chad (Neil Brown Jr.) adds raunchy delight or a highly enthusiastic shade via beverage intake.

8. Chad breathes random adult humor and loud slurpy sounds into awkward conversations. Often considered the male companion to Kelli, Chad is the one to have a good time with, to conduct your baddest behavior damn the consequences. Crude, obnoxious, and juice crazy, Leah’s fiancé (and we’re still waiting to see the mysterious Leah) is a real hoot— although at times misogynistic. He can be serious for just a real hot moment before skirting back to mischievous intentions. Still, where would Lawrence be without his uncouth best friend, Chad? 

Like Tasha (Dominique Perry), so many of us wasted precious moments on those unworthy of our time, our bodies, our hearts. We give and give and expect and expect only to be let down in the end.

7. Tasha was the saucy bank teller who crushed massively hard on the man depositing unemployment checks and false promises into her station. Yes, she came up to Lawrence’s job hoping for more than batteries and a hot sauce partner to share the lunch hour. When she finally received released tension, she felt comfortable enough to be herself despite primarily being a weekend girl. Yet she kept forgiving Lawrence for his misgivings including cheating on her, but the last straw was ditching her at the family BBQ without saying a damn thing. Downright disrespectful. Tasha deserved far better than the F Buddy status Lawrence wanted. 

Rasheeda (Gail Bean) stayed true to herself much to the dissatisfaction of her fellow employees.

6. Rasheeda aka DaDa refused to code switch it up at the white law firm— even heeding Molly’s advice to be less loud and pretty much be quiet— under the radar. Although the bosses generally liked Rasheeda’s a brash, outgoing personality in the interview, she was too much for them at the workplace daily. Makes one wonder if Rasheeda would benefit at the Black law firm that Molly works at now— maybe Molly can put in a recommendation someday. 

Team Daniel (Y’lan Noel) for a win in another lifetime.

5. Daniel— the scorching hot producer and Issa’s former classmate who encouraged her musical talents—was definitely the one who got away in Issa’s love life. He understood Issa much better than most in her intimate circle and supported her when she needed him. Sure he did the most (showing up at her job and an event hosted by her job), he did let her stay at his place when she had nowhere to go (or so she says— sis could have chosen several spaces). Just as they were getting closer and mixed message signal shooting Issa confused him for the last time, Daniel’s out of pocket behavior in Backwards Like, season three’s third episode put a nail on the king’s coffin. However, still think about what it would have been if Issa had reached out to him to help her with the Block Party instead of going over Molly’s head for Andrew—a man she barely knew. 

Dr. Rhonda (Denise Dowse) is the medicine Molly needs in her otherwise chaotic life.

4. Dr. Rhonda kept it one hundred with Molly— something a lot of people aren’t brave enough to do. The “shoulda, coulda, woulda” bogs many hopes for the future. For someone like goal oriented Molly originally hoping for a marriage similar to her parents, Dr. Rhonda easily burst that bubble, advising Molly to live in the moment and not rush to check all the boxes. 

Jared (Langston Kerman) didn’t go to college, but that didn’t mean he wasn’t as smart, confident, and talented as those who did. 

3. Jared was an incredibly layered character that knew what he wanted. Sure a certain ill-humored song performed on open mic night had the Enterprise employed brother flaking (not Molly’s fault), he eventually came back because she interested him. He managed to impress her bourgeois friends at a house party and sweet talked her into an utterly romantic first kiss near a car outside. Eventually sidelined for more sophisticated men, Jared’s patience was tested again and again as fickle Molly continued stringing him along as a potential boyfriend then friend then lover. Although it was unforgettable to have no errands to run after sharing Cookie Crisp cereal, they could not work out due to Jared’s exploration of his sexuality— not Molly’s (who too did some experimentation), just Jared’s. 

Issa (Issa Rae) took a while to find her worth. 

2. Issa was a mess hotter than those flaming red Cheetos. Yet she related on many ways, especially to those who do work mostly white nonprofit organizations that expect minorities to perform better than the average. The first episode contained a heavy, triggering moment— the kids mocking her hair, her accent, her style— this all hit home. Eventually those same kids grew to love Issa because she showed them the benefits in their neighborhood, aspired them to see beyond the typical Black stereotypes (that her own ingrained coworkers saw them as). Relationship wise— Issa stayed with Lawrence longer than she should have, treated Daniel poorly, took Nathan’s “ghosting” inappropriately, and did not listen to Molly’s warning about Condola. Issa does use people to her own needs. However, she takes initiative, builds up her community, and stays focused on bettering herself. 

Cheers to Kelli (Natasha Rothwell), everyone’s number one and most should have her own show in the future. 

1. Kelli is the most dynamic and hands down the most fascinating. She’s the coolest girl in the circle, another bank girl who knows her worth (like eventually Tasha), the one who can crack a spitfire joke and tell you all about yourself in an honestly frank manner. At the same time, Kelli has her vulnerabilities, her moments that tell the audience that she is not only valuable for a personal laugh track. When Kelli and bestie Tiffany were having problems way before Tiffany’s baby arrived, Kelli’s heart was ripped to pieces watching Tiffany surround herself with uppity, fake socialites. In the end, Kelli was there for Tiffany, being a considerable help in Derek’s search and taking care of their baby. She also advises Issa and Molly time to time on their BS. Plus Kelli’s sharp, witty tongue going head to head with Issa’s hilariously shady brother Ahmal (another top notch character) is often brilliant must-see-comedy.