Insecure's Funniest Moments

Issa Rae's "Insecure" began its five-season run on HBO in 2016, based in part upon Rae's web series "The Mis-Adventures of Awkward Black Girl." In the years since, the show has established itself as a classic series, earning many awards and highlighting the Black experience. "I just wanted to see my friends and I reflected on television, in the same way that white people are allowed, and which nobody questions," Rae told The Guardian.

In that same interview, Rae referred to "Insecure" as "a show about regular black people being basic," and perhaps that is why we love it so much. The characters are flawed, complex human beings and the relationships between them are truthfully complicated. And while "Insecure" does drama very well, its comedic moments are some of the true highlights of the series. When Issa Dee (Rae's character) and her friends — especially Kelli Prenny, played by the hilarious Natasha Rothwell — bring the funny, it feels both real and ridiculous all at once. In celebration of "Insecure," here are some of the funniest moments from the show's five seasons.

"Insecure" immediately won us over with its stellar pilot episode, entitled "Insecure as F***." We quickly warmed to Issa Dee, a 29-year-old African-American woman working as a youth liaison at "We Got Ya'll," a mostly white nonprofit targeting underserved minority teens in Los Angeles. Issa is portrayed as unsatisfied at work, as well as at home, where she lives with her partner Lawrence (Jay Ellis), who is unemployed and unmotivated. It's all kind of depressing, but the episode utilized its lighthearted elements to strike a balance between drama and fun.

Viewers did not know what to expect when Issa drags her best friend Molly (Yvonne Orji) to an open mic night to track down her former fling Daniel (Y'lan Noel). So, color us surprised when Issa ends up spitting out a side-splitting rap that would go on to define much of the character's first-season experience. The rap is about a girl with a "broken p***y," who scares men away, and is very obviously about Molly and her struggles. While Molly brushes off the rap quicker than one might expect, it comes back to haunt Issa when her students find it on YouTube. Even though Issa does not rap as much after that first season — and almost never outside of her mirror reflection scenes — we have to give props to "Broken P***y" and how much of an earworm it became.

Some of the best characters on "Insecure" are rather minor, like Issa's opinionated brother Ahmal Dee (Jéan Elie) or her former co-worker, idealistic Frieda (Lisa Joyce). Many of these smaller recurring characters are used for humor, and never has that been truer than with Issa's neighbor, Miles (Tristen J. Winger), known by his nickname, "Thug Yoda." Thug Yoda only appeared in nine episodes of "Insecure," but that did not stop Vulture from putting him atop their 27-character ranking of men from "Insecure."

Thug Yoda's introduction came in the second episode of the show, "Messy as F***," when we learn that he is both a gang member (he is a Blood) and a doting dad. How can one not laugh when Thug Yoda refers to the Care Bears as the "Bare Bears," because, as he told his daughter, "we don't use no C-words, sweetheart"? Thug Yoda had plenty of other strong moments that could have easily made this list, but our runner-up is the scene where he tries to pick up Kelli (Natasha Rothwell) at a house party.

"His ability to just be transparent and to be himself is what people loved," Winger said in a 2021 interview with TVLine. "'Insecure' authentically and unapologetically represented and celebrated South Central L.A., and there is a parallel between that and Thug Yoda. He never sugarcoated anything. He never tried to harm anyone. He just wanted to share his thoughts and replace the C's in words with B's."

Issa's best friend Molly is a highly intelligent woman and a successful lawyer, but a loser in love for many seasons. She is especially bad with men in the first season, and her first beau on the show, Jered (Langston Kerman), seemed to suffer from Molly's standards from the start. First, Molly had an issue with the fact that Jared did not graduate college — and she actually ended things with him in the show's third episode because she thought she could find someone better after being accepted to elite dating app The League. The duo got back together a couple of episodes later, and then Molly broke up with Jered when she found out he had once had a same-sex sexual experience (don't get us started on that).

Jered appeared in seven episodes but took part in few comedic moments. We do, however, have a soft spot for Molly's speech in "Real as F***," wherein she tries to make amends with Jered but totally insults him in the process. It's an example of Molly's judgmental ways and also her inability to say the right thing when it comes to men. After Issa tells Molly that she has "unrealistic expectations" for men, Molly heads to Jered's place to apologize. Jered shuts the door on her, and we are all for it — but still laughed when Molly's "apology" showed how little self-awareness she had. "When it came to us, I should have just lowered my standards," she said. Girl, come on!

If you are shy about sex, you may want to skip this one — but then again, it is hard to be an "Insecure" fan and clam up around sexuality. The show never shied away from integrating sexual experiences into the stories, with a good mix of using sex for both plot advancement and humor. The episode "Hella LA" has — for us — one of the funniest scenes of the entire series, when Kelli hooks up with a man under the table at a diner.

In the episode, the girls go to a day party called "Kiss & Grind," where Issa runs into Daniel, Molly is propositioned for sex by an old friend named Dro (Sarunas J. Jackson) with an open marriage, and Kelli meets a man who asks her to meet up at a restaurant later on. At said restaurant, the guy proceeds to digitally pleasure Kelli under the table, right beside a horrified Issa. The idea is funny, sure, but it's the hysterical Rothwell's facial expressions that do it for us. This is one of Kelli's funniest moments, and that is saying a lot, given the character's ability to steal nearly every scene in which she appears.

Kelli's next great scene comes in Season 3, in the episode entitled "Familiar-Like," which is technically about Issa but totally stolen by Natasha Rothwell's comedic performance. At this point in the show, Issa is staying with Daniel, rent-free, which Kelli simply cannot comprehend. She quizzes Issa on what she's offering Daniel –- turns out, it's nothing –- and concludes that she need not "look a gift horse in the dick." This segment is the best part of the scene, but the whole thing is perfection.

The reason Issa goes to Kelli is for advice on her finances –- because, as ridiculous as Kelli can be, she is also a seasoned accountant. The scene is filled with other fantastic jokes, such as when Kelli explains to Issa just how bad her 425 credit score actually is. "The basic credit tiers are excellent, good, poor, bad ... it's Issa, it's all the way at the bottom," she says, hand gestures included. Kelli also has a bunch of great one-liners, like "You concumbining?," "You buying groceries at Rite Aid?," and "Radio Shack ain't even a store no more." We need a Kelli Prenny spinoff, like, yesterday.

No matter whether you are Team Lawrence or Team Nathan –- or even Team Daniel! –- you have to admit that Issa and Nathan Campbell (Kendrick Sampson) have some electrifying chemistry and that their first "date" makes the episode "Fresh-Like" one of the strongest of Season 3. After meeting in a Lyft in the season premiere, Episode 4 has Issa and Nathan run into each other outside of Worldwide Taco, the taco stand she suggested to him at the beginning of the season. The two then go on an impromptu adventure, which leads to a very funny scene in a pool.

Issa and Nathan walk around South Los Angeles, having candid conversations and playing a game of childhood favorite Truth or Dare. They also add breaking and entering to their list of activities when they visit Issa's childhood house and trespass. They end up naked in the backyard pool –- which is actually a very touching scene, wherein both of them peel back the layers. Issa discloses that she hated her job and wanted to be doing something music-related (she quits her job at We Got Ya'll at the end of the episode, too) and Nathan tells Issa about his lack of relationship experience and how Hurricane Harvey affected him. The poignancy of the scene is, in true "Insecure" fashion, interrupted by some fantastic physical comedy when the homeowners notice Issa and Nathan and run them off.

In 2018, Buzzfeed ranked Season 3's fifth episode "High-Like" atop their list of the best episodes from the first three seasons of "Insecure," and we have to agree with their assessment. "High-Like" is an incredible episode from start to finish, and Natasha Rothwell is a powerful force throughout. We will never forget Kelli's drugged-out, melancholic reaction to Molly's lateness and Tiffany's pregnancy, while staring out the window and laughing to herself. "Who's laughing?," she yelled. "Shut up, it's you."

The true focal point of the episode comes when the crew are at Coachella, where they are supposed to see Beyoncé perform. Kelli, off her rocker on an edible, starts a fight after a girl blocks her view of the stage. The group gets kicked out of the concert, and Kelli rightfully asks the security team, "Why do the whites get to stay?" But her rationality ends there, as she attempts to make a break for it, gets tased in the back, and falls to the ground. "I pissed myself. Don't look at me. Remember me different," she mutters from the ground. And then, somehow, Rothwell tops herself when seconds later, as Kelli is being dragged off the ground by one of Nathan's friends, she stops to pose for a selfie before falling back down into his arms.

From the beginning of the show, Issa and Molly are depicted as having a very complicated relationship. And, sure, there are periods where the two are not talking, but a lot of our favorite "Insecure" moments have them working as a dynamic duo. One great example of this is in Season 3's seventh episode, "Obsessed-Like," where Issa pulls a page out of Molly's book and becomes obsessive over Nathan's lack of text responses.

The comedic sequence in question features Issa and Molly randomly appearing at Nathan's home, under the guise of Molly being there to talk to Nathan's roommate, Andrew Tan (Alexander Hodge). Molly had gone on a date with Andrew, so that was their in — but he probably was not expecting Molly to show up on his doorstep, and he most certainly was not expecting a trenchcoated, pajama-clad Issa. Issa poking around in Nathan's room is great sitcom fun, and we're sad when Molly hauls her away from guessing his computer password. We have seen this kind of thing before on TV, but the way that Rae embodies and embraces Issa's awkwardness make this a standout moment.

Look, we know there is a lot of Kelli on this list, but that is because she is the indisputable comedy champ of the "Insecure" cast. In fact, Bustle even has a list solely devoted to Kelli's best moments –- some of which we have highlighted as well. The storylines on "Insecure" can get depressing, but even in the saddest of moments, Kelli knows how to lift our spirits. In "Lowkey Movin' On," we see the fruits of Issa's labor when she has her first block party. Molly attends but gets upset when she finds out Issa had called in a favor from her boyfriend Andrew, after specifically saying no to Issa asking him for help. But we are not here to talk about the fight –- we are here to celebrate Kelli Prenny, who deliciously fakes being British because she's with a man who thought she was from the United Kingdom.

Kelli's accent is over-the-top and uproarious, as she questions her dude on tacos and laughs with an exaggerated "tee-hee." But it's Kelli's interactions with Issa's brother Ahmal that lead to some of the best lines. As Ahmal and Kelli –- who have been known to trade barbs –- converse at the event in front of her new man, Ahmal tries to poke holes in Kelli's British persona. After he asks her what part of England she's from, Kelli comes back with the following: "I am from Poppycock. It's in ... South Central London. Just a biscuit's toss and a fanny away from Benny Hill." We have not loved a fake Brit that much since Robin Williams as "Mrs. Doubtfire."

We don't see Issa and Molly with many friends aside from Kelli and Tiffany (Amanda Seales) –- save maybe Issa's co-worker Frieda and Lawrence's baby mama Condola (Christina Elmore) -– but that does not mean that they don't try to connect with others beyond their core four. After writing Molly off, Issa attempts to be social in Season 4's "Lowkey Done," after meeting some cool girls at an event that she attends alone. As an aside, this episode also sees Issa give a ride to a paranoid old man who accuses her of wanting to steal his information to give it to the government –- a fantastic scene itself.

On the outs with Molly, Issa decides to go to the "Paint & Sip" event by herself –- kind of sad, but also a sign of Issa's growth in independence and confidence since Season 1. She quickly befriends some women who are there for one of their (Dina, played by Kyla Pratt) bridal celebrations. The women forgot to bring booze, and so they bond over Issa's giant stash of wine. Issa feels amazing with these new supportive friends until they dine and dash on her, leaving her with a giant bill (it's a part of their bachelorette scavenger hunt) and a hole in her heart. It's a sad scene –- and the aftermath, in which Issa goes to her mother, is very poignant –- but also quite funny, especially as we get to see how Issa would like to react by way of an imagination sequence.

Kelli undergoes much growth throughout the final season of "Insecure," and we get to see her totally change by the end of the series, where she is shown in a serious relationship with a baby on the way. Much of this growth comes after Kelly faces her mortality –- something she has to do when she is accidentally labelled as "dead" at the gang's 10-year Stanford reunion. She can't even get a name badge, because the school thinks she died.

Though Kelli is unimpressed by the weird things people remember about her in a video montage, we found them very funny. Kelli being known for an allergy to kale and a dance she did to the GS Boyz' song "Stanky Legg?" That tracks with us. And while we are on the subject of Kelli, shout-out to a few of our favorite comedic moments that did not make the list –- Kelli in her "B.A.P.S." Halloween costume, Kelli unsure as to whether a man she spotted was her ex-boyfriend Quantrell, and her monologue on how Black women don't trust each other. It is well-known that Rothwell improvised many of her lines (per Huffington Post), which makes her standout scenes all the more impressive. "The thing about improv that I really love in scripted television is that it really makes a moment authentic ... You don't know what your scene partner's gonna say but you really have to listen and respond accordingly," Rothwell told Huffington Post, adding that her goal is to make the crew and her scene partners laugh.

Yvonne Orji is a very funny standup comic, so it is a little frustrating that Molly is not the funniest of characters. While Molly has some decent comedic moments, her character has always been much more serious than Tiffany, Kelli, or even Issa. That said, we love when we get funny Molly –- and one of the funniest Molly moments comes toward the end of the series, in the penultimate episode.

Molly is in a good place in "Out, Okay?," as her mother had largely recovered from her stroke and she's happy in her workplace relationship with Taurean Jackson (Leonard Robinson). So, when Taurean shows up to Derek (Wade Allain-Marcus) and Tiffany's going away party with a pack of edibles, she jumps into the deep end with him and gets high. This leads to a couple of truly entertaining moments, like the two of them raiding the caterer's stash of hors d'oeuvres in the kitchen and their hookup in the pantry. Knowing the pair get married in the finale, we can only hope that Taurean and Molly live a happy life full of those kind of hijinks.