The critically acclaimed HBO series Insecure kicks off its fifth and final season on October 24, 2021. Despite many calls to make the show longer (it will never be longer) Insecure is a half-hour comedy that centers around the experience of two young Black women as they navigate dating, their careers, and their friendships.
Season 4 of Insecure focused largely on the latter, examining the friendship between lead characters Issa Dee (played by Issa Rae, who co-created the show with Larry Wilmore, writes it, and is an executive producer) and Molly Carter (played by Yvonne Orji). The show has always been celebrated, but its fourth season served as a particularly welcome respite from a world that often ignores and silences the voices of Black women. Here are some things you might not have known about Insecure.
1. We almost had a very different show from Issa Rae.
Most fans know that Issa Rae found initial fame from her award-winning web series Awkward Black Girl. Following the success of her podcast, the actress/writer/producer was approached by Shonda Rhimes and her production partner Betsy Beers. Rae pitched them a comedy about a woman trying to date image-obsessed Hollywood men titled I Hate L.A. Dudes. When the project eventually fell through, Rae told The New York Times that she felt she had “compromised my vision, and it didn’t end up [being] the show that I wanted. It wasn’t funny anymore.’’ Time passed, new opportunities arrived, and now we have Insecure.
2. Insecure is a love letter to Los Angeles.
Much in the same way that its lead character has found her calling showcasing the best of her community, Insecure has always featured the city of Los Angeles as its own character. The block party episode, for example, featured different vendors from the area, which were chosen by soliciting suggestions from the show’s staff, and also featured performances by local musicians.
3. Insecure has attracted a lot of amazing directors.
Insecure has featured the work of fantastic directors like Debbie Allen, Melina Matsoukas, Stella Meghie, Tina Mabry, Oscar-winner Regina King, and many more. This season Kerry Washington directed the penultimate episode titled “Lowkey Trying.” Washington tweeted about her time working on the show, saying: "I've been a huge fan of Insecure since the jump. This is a show that showcases our full humanity. Our beautiful joys & struggles. Our culture, our neighborhoods. Our rich alive Blackness. To direct this show was a privilege! I'm so proud to be part of the @insecurehbo family."
4. Natasha Rothwell is pulling triple duty as writer, producer, and actress on Insecure.
The multihyphenate Natasha Rothwell was on the writing staff of Insecure when she was asked if she would like to play the newly created character (and future fan favorite) Kelli—and the rest is comedy gold. This season’s “Lowkey Happy” was her first solo writing credit on the HBO comedy.
5. Insecure’s show within the show, Looking For Latoya, also has a fictional podcast episode.
Each season of Insecure has included a show within the show that both the characters and the viewers enjoy, from the forbidden slave romance soap Due North, inspired by a writer’s room joke, to Kev’yn, a spoof on '90s TV sitcoms and recent nostalgic reboots. Season 4 featured the mockumentary series Looking for Latoya, a satirical look at the ways that missing Black women are often ignored. It was such a hit, they created a fictional podcast episode.
6. The character of Molly Carter was inspired by a friend of Issa Rae’s.
Yvonne Orji embodies the smart, funny, beautiful, and sometimes aggravating Molly Carter. In the animated short for HBO Backstories, Orji chronicled her journey as a comedian and actress, and humorously revealed that Molly is loosely based on one of Issa Rae’s friends. (Here they are meeting each other.)
7. Solange is a musical consultant for Insecure.
Insecure never disappoints when it comes to the music, and with Solange as a musical consultant it is no surprise. She got involved with the show through Melina Matsoukas, who directed one of her videos. The show frequently showcases up-and-coming artists like Sonny747, St. Panther, Kirby, and many more.
8. Insecure’s wardrobe department works with several up-and-coming Black designers.
Insecure’s costume designer Shiona Turini does a fantastic job capturing aspects of the American black experience for all of the characters with looks like Kelly’s B.A.P.S. costume to Tiffany’s baby wearing a Future AKA hat. This extends to the designers used on the show.
“Not only is it important to me to buy from and support the network of Black and, often, independent designers in the industry, but it's also equally important to our characters,” Turini told Teen Vogue. “They're 'just like us'—diligent, mindful shoppers who are knowledgeable about the importance of supporting Black-owned businesses.” Some of her favorite pieces have been the vintage T-shirts from BLK MKT Vintage and No Sesso.
9. The character of Andrew was almost Australian (sort of).
Alexander Hodge, who plays Molly’s new boyfriend Andrew, is Australian. Hodge recalls that during his chemistry read with Yvonne Orji, Orji learned he was Australian, which prompted her to stop the audition, and launch into a conversation with Issa about whether Andrew should now be Australian while Prentice Penny, the co-showrunner, ate his lunch and waited for the two of them to finish. Ultimately, because the show is a love letter to L.A., it was decided that Andrew had to be American.
10. Insecure’s fifth season was written during quarantine.
While the COVID-19 pandemic has caused delays to the production and release dates of several movies and TV series, the Insecure team wrote the show's fifth and final season from the comfort of their own homes. In an interview with Variety, Rae said that the writers got to work on the new season in early May 2020, albeit virtually.
“I think we have a really good room where people are very, like, sensitive to people speaking,” Rae said of connecting with her team remotely. “We implemented a hand-raising policy just because. That’s the other hard part, like we’re such a jokey room, and it is hard to get in there with the jokes. So we’re finding our rhythm, but it’s still really fun.”
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