Who Was the Best Character on 'Insecure'? Ranking Them From Worst to Best

Insecure is a generational show that meant the world to a lot of people. 

The hit HBO series premiered in October 2016 and introduced most of us to Issa Rae, who served as the show’s star, writer, and co-creator. While some were familiar with her from her YouTube series The Mis-Adventures of Awkward Black Girl, Insecure put her on the map in a massive way.  

People from all backgrounds and ages gravitated to the show, but it hit home for a lot of twentysomethings and thirtysomethings who were still finding their way like so many of the characters on the show. The start of the series finds Issa in a dead-end job and a five-year relationship with unemployed and unmotivated boyfriend Lawrence (Jay Ellis). Issa’s frustration with her life and her boyfriend causes her to act out of character, and she cheats on Lawrence with a high school friend. And that situation split viewers into two categories: Team Issa and Team Lawrence. 

Later in the series, Issa and Molly are butting heads, and it once again leaves viewers picking sides. People argued Sunday after Sunday about who was to blame for the dissolution of the relationship and the friendship, and at the time, Insecure was one of the shows that inspired the most communal discourse online. Viewers hadn’t identified so strongly with characters in a show since Sex and the City, and there were more than enough hilarious and relatable people to choose from in Insecure. 

Recently, HBO’s parent company Warner Bros. Discovery entered a co-exclusive licensing agreement that brought the show to Netflix. The move to the streaming platform introduced Insecure to a new audience that perhaps didn’t have HBO when it was airing or were maybe too young to watch. That has sparked conversations yet again about who are the best and worst characters in the series. 

Were you Team Issa or Team Molly? Team Kelli or Team Ahmad? We looked back at some of the most important characters in Insecure and chose our favorites, and we ranked them from worst to best.

Played by: Sarunas J. Jackson

This show is not about good guys vs. bad guys, but if there were to be a villain in my eyes, it would be Dro. Sarunas J. Jackson played the role of Dro, who was one of Molly’s childhood friends. At first, the two share a deep familiarity between them that makes you wonder why they didn’t end up together. He knows Molly’s intimacies and is aware of her fear of ending up alone, but instead of helping, he uses them to prey on her—and they begin a sexual relationship. He says he and his wife, Candice (​​Gabrielle Dennis), are in an open marriage, a fact that Molly nor the show ever seems to confirm. At one point they have sex inside a bathroom at an event his wife is at, and it truly doesn’t get lower than that. That alone lands Dro firmly at the bottom of our list. —Karla Rodriguez

Played by: Christina Elmore

Condola got caught up in the middle of two people who deeply loved each other but weren’t ready to accept it. She seemed like a good match for Lawrence and perhaps would have been a good friend to Issa, but in the end, she was neither. Once she found out that they had a past, Condola ghosted Issa about a project she really cared about, all because of Lawrence? That proved that Conodola isn’t a girl’s girl like Issa is, and in the end, when she had Lawrence over for a Friendsgiving, it was clear that they also weren’t a good match.

For those viewers who were rooting for Issa and him to get back together, Condola was the only thing in their way, and it only made it worse when we find out she is pregnant with Lawrence’s child. Things were starting to turn between Issa and him, and the pregnancy news derailed their reconciliation. While she didn’t deserve the way he treated her when he found out, her choosing to have the child then became a barrier between the protagonist and her guy. Christina Elmore’s character inspired a ton of memes and jokes about how negatively people felt about her. There wasn’t anything necessarily wrong with Condola if we’re being frank, but she just wasn’t our girl Issa. —Karla Rodriguez

Played by: Amanda Seales

Tiffany is the prototype of every fashionable bougie best friend you love to hate. It was hard to miss the ongoing shade that Amanda Seales’ character delivered whenever she was in a scene with girlfriends Issa, Molly, and Kelly. In her initial introduction, Tiffany is a superficial diva, self-absorbed, and selfish friend. The birth of her daughter in Season 5 gave audiences a more vulnerable Tiffany DuBois as she struggled with postpartum depression. While Tiffany may present as a perfectionist with minimal flaws, it was nice to see her layers peeled back over time.  —Keasya Hudgins

Played by: Wade Allain-Marcus

Often overshadowed by Tiffany’s high-maintenance, over-the-top personality, Derek DuBois somehow remains the perfect husband and friend. Compared to some of the other men of Insecure, Derek is a true gem amongst fools. Though it has been alluded to him stepping out on his wife, Tiffany, at some point, it was never fully addressed. Played by Wade Allain-Marcus, Derek is always there to give Lawrence and the other fellas rational advice, all while holding them accountable for all the foolishness that took place in and out of their relationships. As if he couldn’t be any more of a saint, he stepped up when Tiffany was experiencing postpartum depression and enlisted the girls to help find her when she disappeared. If there was ever a character that deserved more of a storyline of his own, it was Derek DuBois. —Keasya Hudgins

Played by: Neil Brown Jr.

Neil Brown Jr. played the funny and inappropriate Chad Kerr, Lawrence's best friend. Though he is only a recurring character on Insecure, you feel his impact. Chad’s funny one-liners, witty responses, and natural ability to make you question the logic in relationships make him the best friend everyone needs in their life. Maybe he doesn’t always give Lawrence the best relationship advice, but he never fails to make the audience laugh whenever he’s in a scene. Next to Kelli and Ahmal, Chad ranks as Top 3 Insecure funny guys. Issa, if you’re reading this, it’s never too late to give us a Chad Kerr spinoff. —Keasya Hudgins

Played by: Alexander Hodge

Andrew, better known as Asian-Bae, had a slow start on the show. Initially, he was introduced as a friend of Nathan but quickly made his presence known with his pursuits of Molly. Of course, in true Molly fashion, she found a million reasons not to give him a chance before starting a relationship in Season 4. Andrew, portrayed by Alexander Hodge, was a breath of fresh air for Molly. He’s a well-rounded character amid the messy bunch. Andrew brought charm, humor, and sensibility, and challenged Molly to grow up and deal with her toxicity. —Keasya Hudgins

Played by: Jean Elie

Making his first appearance in Season 2 of the series, Issa Dee’s brother Ahmal quickly became a fan favorite. Between his ongoing feud with Kelli, witty one-liners, and perfect comedic timing, Jean Elie brings the funny anytime he’s on your screen.  Many argue that his character deserves more moments throughout Insecure’s five-season run. Seeing Issa and Ahmal’s rare but sweet and endearing sibling moments make you love him even more. If there was ever going to be a spinoff of Insecure, please let it be one starring Ahmal and Kelli. I think we would all tune in for that kind of comedy every week. If we was on the show, he would have definitely ranked higher on this list. —Keasya Hudgins

Played by: Kendrick Sampson

One time for the Houston Hotties! Kendrick Sampson and his beloved Insecure character Nathan brought the Southern charm to the LA gang. The Houston native made his Insecure debut in the third season as Issa’s new love interest. The pair had instant chemistry in Issa’s Party Lyft, leading to the infamous Coachella Ferris wheel hook-up and a romantic affair that was going well, until he ghosted her. Eventually, it is revealed that Nathan had returned home to Houston to get treated for his bipolar disorder. His mental health becoming a topic of conversation added more substance to his character, and the show as a whole. Even though they didn’t end up together, Nathan was a great addition to the show, and once he had himself figured out, he would've been a solid parnter to Issa. —Keasya Hudgins

Played by: Jay Ellis 

Lawrence Hive—stand up! Jay Ellis’ character, Lawrence Walker, is Issa Dee’s on-again, off-again boyfriend, eventually turned husband. In Season 1 of Insecure, we saw an unemployed, unmotivated, self-loathing Lawrence. I’m pretty sure Best Buy owes him for the popularity he brought to the company after a short stint working there during the first season. Over the years, Lawrence copes with heartbreak and depression by leveling up in his professional career, dating more women—some questionable at times—and even becoming a father.

While he started his single era a bit recklessly (even catching an STD), and it led to him having a baby, he stepped up to his responsibilities. His rebound situationship with Tasha and fling with Condola eventually led him back to winning Issa’s heart again. Though there’s still a debate on whether the two should have ended up together, the show concluded on a high note for them. While he had a rough start on the show, Lawrence’s journey made him one of the most likable and relatable characters. —Keasya Hudgins

Played by: Y’lan Noel

We get it Issa, we do. Between his infectious smile, seductive eyes, and charming personality, Daniel King, played by Y’lan Noel, had the girls ready to risk it all. We all have that one person from our past who makes us wonder, “What if?” Daniel certainly was Issa’s what-if guy. The aspiring music producer was one-third of the show’s messiest storylines. During Season 1, Issa conveniently found herself running into ex-flame Daniel while she and Lawrence were experiencing issues in their relationship.

After the breakup, Daniel let Issa stay with him (out of all her friends and family, she chose to go to him for help). While she insisted that she just wanted to keep things casual between them, he didn’t hesitate to run to her side when she got into a car accident. That says a lot about him as a man, and how he felt about Issa. Throughout his time on the show, Daniel’s character was caught up in all of Issa’s drama, not allowing much time for us to get to know his backstory. Oddly enough, we never needed more than that if his one job was to show up for Issa and be eye candy for the audience—a job well done. —Keasya Hudgins

Played by: Yvonne Orji

Molly certainly isn’t the first know-it-all Black female lawyer who's brought humor, sass, and wit to your TV screens, but the Insecure character has left a lasting impression on audiences for five seasons. Molly Carter, played by Yvonne Orji, is the best friend and, some would say, soulmate of the Awkward Black Girl herself, Issa Dee. 

Molly’s evolution throughout five seasons of the HBO hit show deserves to be celebrated. Molly began as Season 1’s highly complex, opinionated, and low self-esteem serial dater, who frequently self-sabotaged her relationships, including her friendship with Issa. The duo went through their fair share of ups and downs, including their big blow-up at Season 4’s BLOCC party. Eventually, Molly started going to therapy and digging deeper into her inner turmoil and the issues she had with her parents. Therapy did our girl some good! By Season 5, we were dealing with a self-aware, healed, openhearted, and in love Molly that we eventually came to appreciate. Love or hate her, no one would deny that Insecure would not be the same without her. —Keasya Hudgins

Played by: Issa Rae

Issa was far from perfect, but she tried. She was down on her luck, fresh off a split from a long-term relationship with Lawrence, stuck in a job that didn’t make her happy, while the people around her who seemed to have it all together poked fun at her misfortunes. Issa earned the ire of so many people, especially men, for stepping out on her relationship. While she was wrong, had she not broken up with Lawrence, she wouldn’t have had the motivation to follow her dreams and find herself through her various (and hilarious) dating experiences she had without him. Her friendship breakup with Molly also allowed her to be more independent and to hustle until she became someone her friends could no longer make fun of. Issa found her way. She made a long list of mistakes as a friend, employee, and girlfriend, but she built herself back up slowly.

At times if you found yourself feeling irritated by her actions, it was probably because she was reflecting some part of yourself you also needed to work on. Issa’s moments in front of the mirror were self-reflecting, not only for her but for the people watching her, too. Cheating on Lawrence was a huge mistake, but in doing so she left room for Lawrence to have a child with somebody else—and that alone is punishment enough. Season 1 found Issa feeling insecure about her place in the world. But by the season finale, she is a boss, a wife, and a confident woman who knows what she had to go through to get to where she is. She is not a flawless protagonist, and that’s what makes Issa an endearing and loveable lead. —Karla Rodriguez

Played by: Natasha Rothwell

Choosing Kelli as No. 1 might seem like a surprising choice, but to me? It’s the most obvious one. She wasn’t a main character, but every time Kelli appeared in a scene, the whole episode was better for it. Natasha Rothwell is a comedian at heart, and that funny bone came in handy for this role. Kelli didn’t bite her tongue and didn’t hesitate to be honest with her friends about their shortcomings and their bullshit. She made fun of them, but when it came down to it she was also one hell of a friend. 

When Issa was struggling financially, it was Kelli who sat down with her to go over her finances and help her come up with a plan. When Tiffany gave birth (and was secretly dealing with postpartum depression) it was Kelli who would go over and lend a hand. At Coachella, Kelli caused a scene and got tased by security for our entertainment. While her friends (aside from Tiffany) were having dating issues, Kelli kept things fun and light, but when love came knocking she didn’t shy from it—she leaned in. She was dead set on not having children, but in the end, she softened up when she found the right man. Rothwell made Kelli a fan favorite with her outstanding performance, and made it clear that she was also the most solid corner in Issa’s group of friends. —Karla Rodriguez