9 Things We Learned From 'Insecure: The End' Documentary

Insecure might be gone for good but the show’s legacy will live forever. 

The thirty minute adventures of Issa Dee, Molly Cater, Martin Lawrence Walker and their friends not only permanently changed what television could look like; they ignited careers and sparked dreams. 

Following the finale of the beloved comedy HBO Max released Insecure: The End, a brief documentary special that chronicled the show from idea, to inception, to impact. 

The special featured exclusive behind-the-scenes footage from the production of the fifth and final season of the show, and detailed stories about the long development process. It included a series of exclusive interviews with actors, producers, writers, drivers and the unsung heroes in the hair and makeup trailers who expanded the ideas of what is elegant and beautiful with every brush stroke. 

It also explored the Los Angeles neighborhoods that the show portrayed lovingly throughout its run which are rarely celebrated on camera and often reduced to a few choice new events.

Spend more time with Molly, Issa, Tiffany, Kelli and the brace faced hater who kept dragging Issa in the mirror by watching Insecure: The End. See 9 things we learned from the special below.

01

We Can Thank Gina Prince-Bythewood For Our Sunday Night Laughs

Rae revealed that after spending high school studying theater, she was more interested in creating movies than serialized content. “I was super into film because of Love & Basketball specifically,” she said. “I wasn’t really thinking about TV because TV wasn’t really that poppin’ then. There just wasn’t enough representation then.”

02

Melina Matsoukas Donated Her Own Wardrobe Due To A Lack Of Season 1 Funds

Elite costume designer Shiona Turini might have been draping the characters in Off White and Hanifa in the later seasons but in the beginning they were shopping the crew’s closets. Director Melina Matsoukas shared that the sparkly teal dress clinging to Issa as she shouted about Molly’s “broken p**sy” was actually hers.

03

Episode 507 Features Black Female Designers Exclusively

The glow up was so real for the wardrobe department that Turini was able to dictate that the principles wear Black female designs from head to toe for their night out turned slumber party. “I wanted to try and feature Black female designers for like every aspect from the earrings to the shoes,” Turini said. “It presented a lot of challenges but at the same time it really gave us an opportunity to champion and support Black female designers.”

04

There’s A Connection Between Insecure And Martin

Vonda Morris, one of the people responsible for serving us effortless 90s glam on Martin gives Issa Dee her glow on Insecure. “I’m old school,” joked Morris, who also worked on The Bernie Mac Show. Seasoned Black professionals continuing to work? We love to see it!

05

Prentice Penny Got His Job With A Letter

The showrunner penned a letter to the up and coming writer and producer Issa Rae to express his vision for their partnership. The unexpected move was successful and Rae called him “my brother,” in one of her last addresses to the cast and crew.

06

Issa’s Hair Isn’t Scripted

Unlike wardrobe and location, the hair for Rae’s character is often a spontaneous decision by veteran hair stylist Felicia Leatherwood. “I don’t plan these styles you guys,” she said. “They literally are a creation between Issa and I in the morning,” Leatherwood said. “Sometimes I have an idea of what I want but once I see the wardrobe it could change, so yeah, its off the cuff.”

07

Issa And Molly Were Not Always The Show’s Central Relationship

When Rae was writing outline after outline in development, it was in a meeting with producers that she began was talking about her real-life friendships and showed them a text from her homegirl. The response? “That’s the show.”

08

You Can Literally Count The Show’s Impact

Insecure’s legacy will be felt in film and TV credits for years to come. Co-executive producer Deniese Davis broke down just how impactful it has been in the lives and careers of those the industry often overlooks. “In five seasons we’ve given eight first-time directors the opportunity to direct their first episodes of tv,” she said. Showrunner Penny added: “Seven writers over the last five seasons go on to get their own overall deals, we’ve seen six of our writers from these five seasons go on to become showrunners post-Insecure. We’ve hired and broken in two costume designers, a new DP (director of photography) to television.” He says, “We tried to open as many doors as possible.”

09

The Show Changed The Tide For Than Creatives In Hollywood

It’s difficult to thrive in the entertainment industry off the page as well. Anthony Sims, a driver on Insecure who once connected with Rae at a 7/11 explained how working with Davis on another show put him back in Rae’s orbit and helped him earn days towards his union card. “Fast forward I got a call and it worked out,” said Sims. “This show means so much to me, it’s helping me take care of my family. I can go home and look at my wife and she’s proud of me.”

TOPICS:  HBO Insecure Insecure Issa Rae Yvonne Orji