Character Guides Insecure Cast and Character Guide

Insecure Cast and Character Guide

A cast and character guide for HBO series Insecure featuring who plays who, information about each character, and other noteworthy information about the show.

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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.

Issa

Issa Dee (Issa Rae) working on her computer.
Issa Dee (Issa Rae)

Played By Issa Rae

First Noted In – Season 1, Episode 1

Brief Description

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
  • 3.4: Issa’s parents divorced when she was 16
  • 3.8: Turns 30
    • 4.6: Still 30

Quotes


Lawrence

Lawrence gets pulled over after an illegal u-turn
Lawrence gets pulled over after an illegal u-turn

Played By Jay Ellis

First Noted In – Season 1, Episode 1

Brief Description

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

Quotes


Molly

Molly (Yvonne Orji) talking to Issa.
Molly (Yvonne Orji)

Played By Yvonne Orji

First Noted In – Season 1, Episode 1

Brief Description

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
    • Speaks Spanish
  • 2.3: Has multiple brothers
  • 2.5: Her relationship goals are based on her parents who have been together for 35 years.
    • Her mother’s name is CeeCee

Quotes


Joanne

Joanne (Catherine Curtin) listening to a presentation.
Joanne (Catherine Curtin)

Played By Catherine Curtin

First Noted In – Season 1, Episode 2

Brief Description

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.

Additional Information About Joanne

Quotes


Frieda

Frieda (Lisa Joyce) giving a presentation with Issa.
Frieda (Lisa Joyce)

Played By Lisa Joyce

First Noted In – Season 1, Episode 3

Brief Description

Frieda is Issa’s partner at “We Got Ya’ll” and often is the only one in her corner.

Additional Information About Frieda

Quotes


Jered

Jered (Langston Kerman) without a shirt on.
Jered (Langston Kerman)

Played By Langston Kerman

First Noted In – Season 1, Episode 3

Brief Description

One of Molly’s love interest in the series who didn’t go to college and works at a car rental place (Enterprise).

Additional Information About Jered

  • 1.6: Reveals he is bi-sexual

Quotes


Kelli Prenny

Kelli (Natasha Rothwell) pouring drinks for Issa's party.
Kelli (Natasha Rothwell)

Played By Natasha Rothwell

First Noted In – Season 1, Episode 3

Brief Description

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.

Additional Information About Kelli

  • 1.8: Is 30

Quotes


Tiffany

Tiffany (Amanda Seales) smiling towards Issa.
Tiffany (Amanda Seales)

Played By Amanda Seales

First Noted In – Season 1, Episode 3

Brief Description

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

Quotes


Rasheeda

Rasheeda (Gail Bean) talking to Molly.
Rasheeda (Gail Bean)

Played By Gail Bean

First Noted In – Season 1, Episode 3

Brief Description

A co-worker of Molly’s at her firm who decides not to code-switch, which means her being very boisterous and, in Molly’s mind, too hood.

Additional Information About Rasheeda

Quotes


Tasha

Tasha (Dominique Perry) cashing Lawrence's unemployment check.
Tasha (Dominique Perry)

Played By Dominique Perry

First Noted In – Season 1, Episode 3

Brief Description

A bank teller that Lawrence knows that shows an interest in him.

Additional Information About Tasha

  • 1.4: Has aspirations to become a bank manager

Quotes


Issa’s Other Co-Workers at “We Got Y’all”

Sujata Day, Mason McCulley, and Veronica Mannion having a conversation about Issa's project.
Sujata Day, Mason McCulley, and Veronica Mannion

Played By Veronica Mannion, Mason McCulley, and Sujata Day

First Noted In – Season 1, Episode 3

Brief Description

The people who make Issa hate her job at “We Got Y’all” due to either saying some low-key racist things or coming off as skin folk but no kinfolk.

Additional Information About Issa’s Other Co-Workers at “We Got Y’all”

Quotes


Daniel

Daniel after eviscerating Issa.

Played By Y’lan Noel

First Noted In – Season 1

Brief Description

Issa’s ex who comes into her life while things are very rocky with Lawrence, thus causing confusion and bad decisions.

Additional Information About Daniel

  • 1.4: Issa hasn’t really hung out with him in 5 years.
  • Season 1: Is a music producer.

Quotes


Hannah

Hannah (Heather Mazur) talking to Molly.
Hannah (Heather Mazur)

Played By Heather Mazur

First Noted In – Season 1, Episode 4

Brief Description

One of the partners at the firm Molly works in

Additional Information About Hannah

  • 2.2: Has transitioned to the Chicago office

Quotes


Chris

Chris (Jidenna) on a date with Molly
Chris (Jidenna)

Played By Jidenna

First Noted In – Season 1, Episode 4

Brief Description

A lawyer Molly meets and hits it off with.

Additional Information About Chris

Quotes


Chad

Chad (Neil Brown Jr.) talking to Issa.
Chad (Neil Brown Jr.)

Played By Neil Brown Jr.

First Noted In – Season 1

Brief Description

Lawrence’s best friend who he relies on when things with Issa go south.

Additional Information About Chad

Quotes


Dr. Rhonda Pine

Dr. Rhonda Pine (Denise Dowse) having a session with Molly.

Dr. Rhonda Pine (Denise Dowse)

Played By Denise Dowse

First Noted In – Season 2, Episode 1

Brief Description

Molly’s therapist.

Additional Information About Dr. Pine

Quotes


Ahmal

Ahmal (Jean Elie) greeting his sister.
Ahmal (Jean Elie)

Played By Jean Elie

First Noted In – Season 2, Episode 1

Brief Description

Issa’s gay brother who does a little bit of this, a little bit of that, to get by.

Additional Information About Ahmal

  • 2.1: Has beef with Kelli but loves him some Tiffany.
  • 4.5: Is verse

Quotes


Renee

Renee (Leshay Tomlinson) smiling at Molly.
Renee (Leshay Tomlinson)

Played By Leshay Tomlinson

First Noted In – Season 2/ Episode 2

Brief Description

One of the assistants for the partners at Molly’s firm who aides her into breaking into the boys club.

Additional Information About Renee

Quotes


Vice Principal Gaines

Vice Principal Gaines (A. Russell Andrews) trying to talk to Issa and Freida while getting work done.
Vice Principal Gaines (A. Russell Andrews)

Played By A. Russell Andrews

First Noted In – Season 2/ Episode 2

Brief Description

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

Quotes


Eddie

Eddie (Leon Thomas) talking to Issa.
Eddie (Leon Thomas)

Played By Leon Thomas

First Noted In – Season 2, Episode 3

Brief Description

One of the people Issa hooks up with in the second season.

Additional Information About Eddie

  • 2.3: Enjoys watching “Gossip Girl.”

Quotes


Lionel

Lionel (Sterling K. Brown) on a date with Molly.
Lionel (Sterling K. Brown)

Played By Sterling K. Brown

First Noted In – Season 2, Episode 3

Brief Description

What appears to male version of Molly thanks to him having a 5 year plan, wanting kids in the future, and his ish together.

Additional Information About Lionel

  • 2.3: Is a marketing consultant

Quotes


Quentin

Quentin (Lil Rel Howery) during a Skype call.
Quentin (Lil Rel Howery)

Played By Lil Rel Howery

First Noted In – Season 2, Episode 3

Brief Description

One of the members of the Chicago office for the firm Molly works at who tries to get close to her.

Additional Information About Quentin

Quotes


Dro

Dro (Saruna J. Jackson) at a anniversary celebration for Molly's parents.
Dro (Saruna J. Jackson)

Played By Sarunas J. Jackson

First Noted In – Season 2, Episode 3

Brief Description

Molly’s childhood friend who claims he is in an open relationship when he and Molly begin to mess around.

Additional Information About Dro

  • 2.4: He and Molly kissed in middle school

Quotes


Candice

Candice (Gabrielle Dennis) and Dro (Saruna J. Jackson) smiling together.
Candice (Gabrielle Dennis) and Dro (Saruna J. Jackson)

Played By Gabrielle Dennis

First Noted In – Season 2, Episode 3

Brief Description

Dro’s wife who, to some surprise, initiated the idea of her and Dro having an open relationship.

Additional Information About Candice

Quotes


Derek

Derek (Wade Allain-Marcus) having lunch with Lawrence.
Derek (Wade Allain-Marcus)

Played By Wade Allain-Marcus

First Noted In – Season 2, Episode 5

Brief Description

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.

Quotes


Aparna

Aparna (Jasmine Kaur) smiling at Lawrence.
Aparna (Jasmine Kaur)

Played By Jasmine Kaur

First Noted In – Season 2, Episode 6

Brief Description

Lawrence’s co-worker who helps him understand the culture of his new job and becomes his girlfriend.

Additional Information About Aparna

  • 2.7: It should also be noted she is an app developer.

Quotes


Nico

Nico (Diego Serrano) on a date with Issa.
Nico (Diego Serrano)

Played By Diego Serrano

First Noted In – Season 2, Episode 5

Brief Description

One of the people in Issa’s season 2 ho-tation that appears to want an actual relationship.

Additional Information About Nico

Quotes


Nathan (Kendrick Sampson)

Nathan explaining what happened to him for a month.

First Noted In – Season 3/ Episode 1 “Better-Like” [Season Premiere]

Brief Description

Issa’s love interest in season 3, who she meets as she works for a ride-sharing app.

Additional Information About Nathan

Quotes


Antoinette (Karen Obilom)

Antoinette (Karen Obilom) being interviewed by Issa and Frieda.
Karen Obilom as Antoinette.

First Noted In –Season 3/ Episode 3

Brief Description

A new employee at “We Got Ya’ll” who sparks the idea that Issa’s time at the job should probably end.

Additional Information About Antoinette

Quotes


Taurean (Leonard Robinson)

First Noted In –Season 3/ Episode 4

Brief Description

Molly’s rival at her new firm who she constantly bumps heads with.

Additional Information About Taurean

Quotes


Stacy (Nikiva Dionne)

First Noted In – Season 3/ Episode 4

Brief Description

One of Molly’s new co-workers.

Additional Information About

Quotes


Felicia (Kelsey Scott)

First Noted In – Season 3/ Episode 4

Brief Description

One of Molly’s new co-workers.

Additional Information About

Quotes


Andrew (Alexander Hodge)

Andrew noting he isn't sure how he plays into Molly's life.

First Noted In – Season 3/ Episode 6

Brief Description

 

Additional Information About Andrew

  • 4.1: Works at LiveNation

Quotes


Andy (Harry Lennix)

Andy (Harry Lennix) and Lawrence having lunch.
Andy (Harry Lennix) and Lawrence

First Noted In – Season 3/ Episode 8

Brief Description

Lawrence’s father.

Additional Information About Andy

  • 3.8: Lawrence’s mother is Sylvia.

Quotes


Condola (Christina Elmore)

Condola telling Lawrence that she is friends with Issa.
“I think that I might be friends with your ex.”

First Noted In –Season 3/ Episode 8

Brief Description

One of Tiffany’s peers that ends up friends with Issa and coordinates with her on creating a block party. Also, she ends up dating Lawrence.

Additional Information About Condola

  • 4.1: Works at Highline PR
  • 4.3: Is a divorcee
    • The man who left her is named Mark

Quotes


Sheryl (Paula Jai Parker)

Sheryl (Paula Jai Parker) introducing herself.
Sheryl (Paula Jai Parker)

First Noted In – Season 4 Episode 1 “Lowkey Feelin’ Myself” [Season Premiere]

Brief Description

Owns an alcohol distribution company.

Additional Information About Sheryl

Quotes


Calvin “TSA Bae” (Paul Mabon)

Calvin (Paul Mabon) talking to Issa about the side effects of dealing with a big guy.
Calvin (Paul Mabon)

First Noted In –Season 4 Episode 1 “Lowkey Feelin’ Myself” [Season Premiere]

Brief Description

Issa’s friend with benefits in the early part of season 4.

Additional Information About Calvin

Quotes


Delilah (Wendy Raquel Robinson)

Delilah greeting Issa.

First Noted In –Season 4 Episode 3 “Lowkey Thankful”

Brief Description

Ahmal and Issa’s mother.

Additional Information About Delilah

  • 4.3: Is dating a man named Stanley

Quotes


Celia (L. Scott Caldwell)

Celia (L. Scott Caldwell) giving Molly encouragement.
Celia (L. Scott Caldwell)

First Noted In –Season 4 Episode 3 “Lowkey Thankful”

Brief Description

Molly’s mother.

Additional Information About Celia

Quotes


David (Gregg Daniel)

Molly and David (Gregg Daniel) enjoying Thanksgiving together.
Molly and David (Gregg Daniel)

First Noted In – Season 4 Episode 3 “Lowkey Thankful”

Brief Description

Molly’s father.

Additional Information About David

Quotes


Jerome (Malcolm David Kelley)

Jerome (Malcolm David Kelley) talking smack.
Jerome (Malcolm David Kelley)

First Noted In – Season 4 Episode 3 “Lowkey Thankful”

Brief Description

One of Molly’s brothers who has a whole lot of mouth.

Additional Information About Jerome

Quotes


Curtis (Richard Nevels)

Curtis (Richard Nevels) giving the side eye.
Curtis (Richard Nevels)

First Noted In – Season 4 Episode 3 “Lowkey Thankful”

Brief Description

Molly’s brother who works at keeping the family together.

Additional Information About Curtis

Quotes


Nikki (Robin Thede)

Nikki (Robin Thede) being very drunk.
Nikki (Robin Thede)

First Noted In – Season 4 Episode 3 “Lowkey Thankful”

Brief Description

Condola’s friend who reveals quite a bit about her.

Additional Information About Nikki

Quotes


Victor (Stephen Oyoung) and Lydia (Camille Chen)

Victor (Stephen Oyoung) and Lydia (Camille Chen) being introduced.
L to R: Victor (Stephen Oyoung) and Lydia (Camille Chen)

First Noted In – Season 4 Episode 7

Brief Description

Victor is Andrew’s brother loves to play devil’s advocate and be a bit much. Lydia is Victor’s wife, Andrew’s sister in law, who puts up with it.

Additional Information About Victor and Lydia

Quotes


General Information

Network HBO
Creator(s) Issa Rae, Larry Wilmore
First Aired 10/9/2016

Groups & Organizations

We Got Y’all

Where Issa works early on in the series

Meridian

Where Lawrence works starting midway through the first season.


Notable Locations

The Dunes

Where Issa and Lawrence live in season 1


Terms To Know

Woot Woot

The app Lawrence was working on.


Other Noteworthy Information

Social Media

306,475FansLike
372,284FollowersFollow
142,721FollowersFollow

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Review Summary

Amari Allahhttps://wherever-i-look.com
I started Wherever I Look back in 2011 and from movies, TV, the occasional book, play, and Broadway show, have been trying to bridge the gap between a critic and an avid lover of various forms of media.

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