In Insecure, Issa Dee and her friends take on the challenges that come as they work through their late 20s and early 30s. Issa and characters like Molly Carter have dramatic plotlines with their romantic interests and families. Some fans can't stop speculating who Issa should end up with on Insecure.
However, they also prove to be hysterical as they work through their conflicts with others. Some characters like Kelli Prenny are goofy and easy to recognize as the funniest characters in the series. Issa's other friends like Molly Carter showcase humor that is harder to rank.
Daniel King
Most of Daniel's arc is presented in the first few seasons of the series. He proves to be kind and understanding in his actions. He forgives Issa after she belittles him, and even takes her in when she has no place to stay.
However, his moments on screen are almost entirely dramatic. While Issa's other partners like Lawrence Walker and Nathan Campbell are known to crack jokes, Daniel shines instead with moody peaceful energy.
Nathan Campbell
Nathan is a pleasant guy, and his patience with Issa helps make him one of the more likable characters in Insecure. Although Nathan can be serious, he is no stranger to jokes and he and Issa riff with each other multiple times in the series. When the two first meet, they exchange jokes about Chad Kerr's bench billboard.
However, Nathan is more dramatic than he is funny. His arc has to do with serious issues like mental health and his tumultuous relationship with Issa. While some of Issa's other partners like Lawrence exude a funny aura, most fans would call Nathan smooth. He rarely puts himself in a situation where he acts silly.
Taurean Jackson
Taurean is almost always serious in Insecure. He is Molly's co-worker, and the two don't get along during the first few seasons of the show. However, they become romantically involved in the final season. Taurean doesn't have too many funny moments. However, in the penultimate episode of the final season, he is hilarious.
When he comes to a party with Molly, he brings the wrong party favors. His insecure reaction, telling the hosts he is going to put his gift in the trash, is one of the funniest bits of the season. For funny moments, what Taurean lacks in quantity he makes up for in quality.
Tiffany DuBois
Tiffany is one of Insecure's smartest characters and is one of the most stable women in Issa's group. However, she is the least comical of her friends. Tiffany isn't without humor, but the stakes are high considering the other characters. She has her moments of hilarity, like when she has too much fun at Coachella.
However, for the most part, Tiffany seems to be unconcerned with the funny and silly. Her world seems almost like a model of a secure life to her friends. She exchanges jokes with them and certainly has fun. However, her relentless focus on a strong family and stability over amusement makes her less funny than her peers.
Molly Carter
Molly is Issa's best friend and has a good sense of humor accordingly. Molly's life is wrought with drama and she shares similar goals of security as Tiffany. However, Molly knows how to be silly, and is almost always cracking jokes with Issa. Furthermore, Molly gives fans funny moments outside of the jokes she makes.
Molly is funny when she lets loose. When she parties at Coachella and vents to strangers about the problems after a few drinks, among other things, it makes for one of her funniest scenes. When she goes to a work event, she finds out in the morning that she dances the night away in a hilarious sequence. When Issa wants Molly to role play her apology to Lawrence, her explosive outburst is hysterical. Her funny moments are hard to quantify.
Martin Lawrence Walker
Lawrence is one of the most beloved characters in the series. Saying Lawrence is a villain on Insecure is one of fans' most unpopular opinions. He is the first partner for Issa that viewers are introduced to, and he has the humor to match Issa's perpetual joke-cracking.
While Issa has a tendency to go after more serious men like Daniel, Lawrence often showcases his goofy side. He and Issa make jokes together, but also do acts of physical comedy when they joke around. However, Lawrence's most humorous moments come from the jokes he makes with Issa and his other friends like Chad Kerr.
Kelli Prenny
Kelli is Issa's funniest friend. She is known for making jokes but also shows her funniness in her behavior. Her wild partying often makes for hysterical moments. However, she still cracks audiences up even after she mellows out in the final season. Kelli's funny moments are almost too many to name.
During one of Issa's events, Kelli puts on a fake British accent to seem mysterious to potential partners in one of her most subtle comedic moments. When she is tased at Coachella, she gives audiences perhaps her most outrageous funny scene. However, Kelli's funny bits are so plentiful they show up in every scene she's in. As such, audiences expect it, and some of the surprisingly hilarious moments from other characters make them funnier.
Chad Kerr
Chad is Lawrence's pal, and they often get together to do things like watch sports or help install Lawrence's new TV. However, along the way, some of Insecure's most hilarious quotes come to pass. Chad makes every line he has shine and has funnier quotes than some of the show's most developed characters.
Chad's blunt delivery for almost everything he says underscores his funny comments. Chad isn't the goofiest man in the series, and his funniness comes from the things he says. However, he doesn't present much goofy behavior, leaving him lower on the list than some of his peers.
Issa Dee
Issa is the main character audiences see in Insecure, and she is one of the funniest personalities in the series. Her awkward moments not only present the show's namesake but also showcase a seemingly endless string of funny moments. Issa is funny when she tries to be, but even funnier when she doesn't.
Perhaps the deepest well of hysterical moments from Issa comes from her raps. When she spits rhymes about her life to herself in the mirror, they present her inner conflict. However, the anger, fear, and shame of her decisions come to pass in the raps and are hilariously spoken with the levity of a fun rhyme. The contrast of the venue for which Issa deals with her issues and the severity of the problems make for some of the funniest bits in the show.