A cast and character guide for HBO series Insecure featuring who plays who, information about each character, and other noteworthy information about the show.
Please Note: This content contains pertinent spoilers, descriptions are updated as new information is presented, images changed as better ones are captured, and this is not an exhaustive list of every cast member, guest star, or reoccurring role.
When we first meet Issa, she is 29, from a good family, works at a non-profit, and has been with her boyfriend, Lawrence, for 5 years. However, despite things being okay, considering how her friends are flourishing and she feels like she is on a steady decline, slowly, but surely she shakes things up. Sometimes in productive ways and other times in ways that just causes unnecessary drama.
Additional Information About Issa
3.3: Had been at “We Got Ya’ll” for approximately 5 years
Issa’s boyfriend at the beginning of the series who is one of those dude with vast potential that never came into fruition. But, as he and Issa have issues, and he is forced to look at himself and focus on his development, things change for him. Sometimes for the better, at times for the worse, but it is made clear that he and Issa were a bit stunted thanks to the other person.
Additional Information About Lawrence
1.3: Went to Georgetown
2.5: Was unemployed 2 years
3.6: Is around 32.
4.2: Actual name is Martin Lawrence
4.8: Parents are Marcus and Sylvia
4.8: Explains why he broke down and became a bad boyfriend to Issa
4.10: Gets hired for a major job in San Fransisco and learns he is going to become a father
Issa’s best friend who is a corporate attorney, but don’t let that fool you – Molly can codeswitch. Thus allowing her just as much to communicate in the boardroom as she does with those who are blue-collar or don’t wear no collars. But, despite her professional success, she struggles in relationships and is finding it hard to find someone with the potential to become her husband.
Additional Information About Molly
1.3: Is a third-year associate
2.3: Has multiple brothers
2.5: Her relationship goals are based on her parents who have been together for 35 years.
Joanne is Issa’s boss in the early seasons of the show at “We Got Y’all.” From what we see, and are told, while she is well-meaning, she has quite a few blind spots when it comes to her employees and the kids her non-profit are trying to service.
Kelli is part of Issa’s larger friend group and is the eccentric, usually down for whatever, and crazy one. But, despite how out there Kelli seems, she honestly might be one of the few who actually has her life together. At least in terms of what she currently wants.
Tiffany is a bit of the outlier in the group. While Kelli, Molly, and Issa all have a bit of hood in them and are open about their flaws, Tiffany aims for perfection in all aspects of her life. She does through her marriage, her professional life, and often she comes off very bougie.
Additional Information About Tiffany
Season 4: Has a child and deals with Post-Partum Depression.
Vice Principal Gaines gets Issa a major win at the school he runs by funneling people into the program. However, with him mostly focused on the Black kids, and omitting advocating for the Latinx ones which fill the school, Frieda is left uncomfortable.
Additional Information About Vice Principal Gaines
Tiffany’s husband who is a well to do Black man but, honestly, doesn’t say or do much worth noting – beyond being Tiffany’s husband. Well, at least until his friendship with Lawrence is established firmly.
Additional Information About Derek
2.5: He exists well before this season but really was that unremarkable that he didn’t really seem like someone worth noting till now.