Saying Goodbye to HBO's Insecure

Research by Mercedes Gonzales-Bazan and Róisín Chapman

HBO’s Insecure said its final goodbye on Sunday, December 26, 2021. As the series comes to a close, we wanted to give it a proper TLL farewell. The show had its start in 2016 and has since then become a staple for so many TV watchers and has made Sunday nights 100x better! Here we share some insight into the world of Insecure and celebrate, not only the show, but some of the talent behind it!

What is Insecure?

  • Insecure is a half-hour comedy-drama series on HBO, created by Issa Rae and Larry Wilmore. The show follows two best friends, Issa (Rae) and Molly (Yvonne Orji), who met in college and live in South Los Angeles. They’re there with each other as they both try to figure out their lives, from career to social life to romance, and all the tricky moments in between.

  • Characters

  • Issa – (Issa Rae) Starts off the series working for a non-profit but has much larger hopes and visions to help her community. 

  • Molly – (Yvonne Orji) Issa’a best friend. Hot shot lawyer who has a tough time in the love department.

  • Lawrence – (Jay Ellis) Issa’s long term boyfriend, who’s unemployed and lacking confidence in season 1 and his story gets a bit more complicated from there.

  • Ellis also directed episode 7 in season 4

Who is Issa Rae? 

  • Los Angeles-born actor, writer, producer, entrepreneur, and the co-creator of the show. This Sengalese-American mogul studied African & African-American Studies at Stanford; this is also where she began making music videos and creating a web series. After college, she was living in New York City when she was first inspired to create her web series the Mis-Adventures of Awkward Black Girl, which is what launched the creation of Insecure.

  • Mis-Adventures of Awkward Black Girl

    • The comedy web series follows a Black woman named J (played by Rae) through her uncomfortable or embarrassing interactions and situations with friends, love interests, and coworkers. 

    • It premiered on Youtube on February 3, 2011 and gained attention through social media and the blogosphere. The series inspired the core tone of Insecure because of its humor and relatable plotlines.

What makes Insecure stand out from other comedies?

Rae’s creative endeavors tell stories about Black women that are relatable, fun, and not often shown on screen. 

  • Friendship– At the core of the show, it’s a love story of best friendship between Molly and Issa. As a viewer, you see their lowest moments and the strongest moments; these two always find a way to come back to each other even when it feels too far gone. 

    • Insecure portrays the realistic drifts and mends between friends. Issa and Molly’s friendship began in college along with Kelli and Tiffany, so after years of personal evolutions, career changes, and relationships, their dynamics as a quad change too. 

    • The communication and emotional growth between Issa and Molly shows the true depth of the series. These two learn independently how to be better to each other.

  • Workplace frustrations – It shows the women evolving and growing within their careers, with setbacks and successes that make it relatable.

    • The series begins with both Issa and Molly in the midst of workplace complications

      • Issa starts off working for a non-profit and is the only Black person on her staff. The microaggressions are endless.Her passions to enact change in her community expand into other ventures far beyond that first nonprofit role.

      • Molly navigates the pay gap between her and a white man lawyer at her firm, which eventually motivates her to move to an all-Black law firm.

  • Mental health is portrayed through multiple characters. From bipolar disorder to postpartum depression, the show makes a point to give these characters well-rounded and authentic story arcs to depict realistic experiences.

    • Nathan Campbell (Kendrick Sampson) – Issa’s other main love interest starting in season 3. His character has Bipolar disorder and has gotten a lot of praise for portraying conversations about mental illness on the show.

    • Tiffany DuBois (Amanda Seales) – College friend of Issa & Molly. The first of the group to get married and pregnant. She loves to be the most put-together and refined one of the four, but her character evolves through her journey with postpartum depression.

Authentic South LA
South Los Angeles acts as another character in the series. Rae made it a point to pay homage to this area of the city and celebrate it through its imagery.

  • Even Issa the character’s entire career mission evolves into finding ways to uplift and showcase the culture and community that make Inglewood so special. 

  • Whether it be a community event Issa the character throws like the season 4 Block Party or just a dinner with Molly, Rae emphasizes throughout the series how important it is to create safe spaces for Black Angelenos in a city that is evolving rapidly.

The Creatives Behind Insecure
No show is made alone and Issa has an amazing team by her side. Insecure was made possible from talented producers, directors, costume designers, DPs, and more. These are a few people from the Insecure team who inspire us!

  • Prentice Penny – Showrunner and Writer

  • Melina Matsoukas – Executive Producer of Insecure, directed the pilot of Insecure as well as plenty of other episodes throughout the series.

  • Amy Aniobi – Head Writer and Co-Executive Producer of Insecure. She’s written many episodes throughout the series and directed episode 7 of season 5.

  • Natasha Rothwell – Writer and actress in the series. She’s the Supervising Producer, as well as the Director of episode 6 in season 5.

    • Rothwell plays Kelli Prenny, college friend of Issa & Molly.

    • Queen of one liners, she’s an improv comedic genius! An audience favorite for sure!

  • Ava Berkofsky – Director of Photography for 17 episodes and directed two episodes as well.

  • Nena Erb – Editor for 12 episodes of the series.

  • Ayanna James – Costume Designer for 19 episodes

  • Shiona Turini – Costume Designer for 15 episodes 

  • Felicia Leatherwood – Hair Stylist for Rae for the entire series.

  • Yvette Shelton – Hair Department Head for 25 episodes

  • Natalie MacGowan Spencer – Makeup Department Head for 23 episodes

  • Notable Featured Crew 

  • Debbie Allen - Actress, dancer, choreographer, singer-songwriter, director, and producer. Directed season 1 episode 6.

  • Stella Meghie - Writer and Director of The Photograph (2020), starring Issa Rae. Directed season 3 episode 4 and season 4 episode 5

  • Regina King - Academy Award-Winning Actress and Golden Globes Nominated Director. Directed the season 3 finale.

  • Kerry Washington - Actress, Producer, Director. Directed season 4 episode 9 and season 5 episode 5

Insecure's Fan Engagement

The show made waves critically- receiving eight Primetime Emmy Award nominations in 2020 for its fourth season, including a Primetime Emmy nomination  for Outstanding Comedy Series.  but its largest impact is with its fan base whose love and dedication to the series runs deep. 

  • #insecurehbo twitter nights

    • If you’ve ever watched Insecure, you know the best place to be after an episode is Twitter. From live tweets from cast and crew to the memes, the weekly episode discussions can get heated quickly, but the jokes keep everyone laughing long after the episode ends. 

    • Some notable Twitter moments include:

      • Condola (played by Christina Elmore) came with an explosive plot and the memes lived on! The list of nicknames Insecure fans gave her, from Canola Oil to Condominium were endless!

      • #LawrenceHive – This fandom originated to show support for the main man of the show, Lawrence, as they passionately vocalize their love for him above all else in the show. 

      • The Golden Dunes - To lead up to the show's finale, the official account shared the winners of the Golden Dunes, a fake award show created just to celebrate with fans!

Supporting Issa Beyond Insecure

This is far from Issa Rae’s last success or culture-changing show, she’s busy at work in the realm of music, entrepreneurship, and more. 

  • Issa’s other ventures

    • Hoorae 

      • Rae’s media company encompasses all facets of entertainment, from film and TV to digital and audio.

      • This year Hoorae signed a five-year film/TV deal with Warner Media

    • Raedio 

      • In 2019, Rae and her business partner Benoni Tagoe launched this audio company designed to uplift new talent. 

        • Tagoe said, “Raedio includes a publishing division powered by Kobalt, a label in partnership with Atlantic Records, and a music library hosted via Synchtank, as well as music supervision services and live events.” 

    • Project Greenlight

      • Working alongside Alfred Street Industries and Marimax, Issa has established a program to discover and mentor up and coming female directors.

    • Sienna Naturals – This textured hair care brand is co-owned by Issa Rae and Hannah Diop. It’s focused on clean ingredients to improve hair and scalp health— founded by Black women with textured hair and made for people with textured hair.

    • Sweet Life: Los Angeles 

      • Rae executive produced this reality show which aired in August 2021 on HBO Max. It follows a group of Black twenty-something navigating friendships, love, and careers in South LA

    • Upcoming projects

      • Rap Sh*t – Rae is producing this upcoming comedy series for HBO Max, about two Miami-rappers (played by Aida Osman and KaMillion) who are trying to make it in the industry.


Sources:
https://www.newyorker.com/magazine/2021/11/29/the-end-of-insecure-an-art-work-and-a-phenomenon 
https://www.ebony.com/entertainment/what-insecure-means-now-that-its-ending/ 
https://www.vibe.com/news/movies-tv/issa-rae-hbo-rap-shit-668039/ 
https://variety.com/2021/scene/news/issa-rae-reality-show-sweet-life-hbo-max-1235045154/ 
https://www.siennanaturals.com/pages/about-us 
https://www.projectcasting.com/blog/casting-calls-acting-auditions/hbo-project-greenlight/ 
https://www.synchtank.com/blog/meet-the-team-behind-issa-raes-growing-raedio-music-empire/
https://variety.com/2021/tv/news/issa-rae-hbo-max-warnermedia-film-television-deal-1234935944/ http://likearenegade.com/index.php/2020/06/17/condola-what-is-her-real-name-again-the-internet-is-trifling/ 
https://www.bustle.com/p/why-the-insecure-lawrence-hive-needs-to-buzz-off-for-good-11772377 
https://www.culturedmag.com/article/2021/12/21/kendrick-sampson-is-not-done-fighting 
https://blackgirlnerds.com/insecure-season-4-beautifully-reminds-us-black-mental-health-matters/ 
https://www.latimes.com/entertainment-arts/tv/story/2021-12-12/insecure-hbo-season-5-issa-rae-prentice-penny-amy-aniobi-syreeta-singleton 


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