Character Guides Insecure Cast and Character Guide

Insecure Cast and Character Guide

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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.



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.

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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
  • 4.8: Likes Vodka and Prosecco together

Notable Episodes

  • 4.8: Explains why she cheated on Lawrence



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