In Prep For Season 2, ‘Insecure’ Cast & Creatives Talk Favorite Moments

The cast of Insecure. HBO

When the Insecure cast and creatives gathered for a For Your Consideration panel hosted by Deadline, there were many laughs as the crew talked about season one and how their process is evolving in season two, which is now in production in Los Angeles. The panel included executive producer/star Issa Rae, cast members Yvonne Orji, Jay Ellis, and Lisa Joyce, executive producer Prentice Penny, and executive producer/director Melina Matsoukas.

Here’s what we learned:

  1. This crew is generous. The compliments flowed from the jump. Issa Rae commented on her co-star Yvonne Orji, who plays her onscreen best friend Molly, “You meet Yvonne and you want to be her best friend.” Jay Ellis gave props to the writers, saying, “Playing Lawrence is a dream come true. He’s not the typical character you usually see black men written as.” Yvonne Orji agreed, “They make all the characters so real, so juicy and so relatable.”

  2. Season one stories included real-life experiences from both the cast and the writers. Issa Rae said, “Some characters are combinations of people I know.” Prentice Penny elaborated on the process of crafting the show’s seasons, “Issa and I go to a hotel, drink mimosas and talk about the themes we want to explore and the character arcs. Then we bring in the writers and hear what they think and the ideas snowball.”

  3. The panel chose their favorite season one scenes:

–Issa Rae chose the fifth episode because “it was the tipping point.” Prentice Penny added, “Shoutout to (HBO executive) Amy Gravitt. She told us to move the juicy stuff with Daniel earlier in the season; originally we had it near the season finale. Then Issa’s cheating on Lawrence in the middle and we’re painting ourselves into these corners and it was exciting to figure out how to get out.” Issa Rae said it also changed from Issa just kissing her old flame Daniel to having sex with him, “That also opened the entire book because you can only cheat on Lawrence once.”

–Yvonne Orji chose the fight between Lawrence and Issa in episode seven because “it’s so heartbreaking. You really feel Lawrence, especially when he keeps saying, ‘Who? Who?’”

–Jay Ellis loved the season finale scene with Molly and Issa driving back from Malibu, “I enjoyed watching them tiptoe around each other, not directly talking *to* each other but on the same page at the same time. I’ve never gotten to see two black women do that on television.”

–Prentice Penny liked the fantasy sequence in episode four where Issa was in front of a mirror talking to Daniel, a bottle of champagne and the magical appearance of Ty Dolla Sign. Penny described, “The way director Kevin Bray shot it – Issa saw the champagne coming outta there and the laughs and then Ty Dolla Sign appears. It’s this crazy world. Issa is selling it and then Molly stops it when she says, “Have you forgotten about your man?” and Issa says, “I appreciate you, girl” and then it goes into this serious place and takes a left.”

–Melina Matsoukas chose the final montage in the season finale, “When Issa thinks Lawrence will be there (in the apartment) then we cut to Lawrence having sex with Tasha. We end on Issa and Molly, two women on the couch, there for each other.”

  1. Yvonne Orji is a devoted customer of the Dollar Store. Jay Ellis recounted a story of how Orji learned to deal with her newfound fame and being recognized, “She goes to the Dollar Store to get peanuts and ice.” Orji countered, “I am a frugal African.” Ellis continued, “Now her friends go to the Dollar Store for her and drop packages off to her.” Orji laughed and made the Italian chef kiss gesture saying,  “When you’re broke, Dollar Store peanuts are…”
  2. Melina Matsoukas was eloquent when asked why the experience of working on “Insecure” is different, “The material is groundbreaking and I also think the way it’s told is groundbreaking. We’re people of color telling our own stories, coming from different worlds, trusting in each other’s different experiences. There’s no boundary, no line we have to stay on. We all push each other to do better.”
  3. Rae talked about scaling up when she moved from producing web content on “Awkward Black Girl” to working on “Insecure” with a professional television production crew, “When you’re creating content online, you’re the craft services, you’re the talent, you’re directing, producing, doing all those things and not necessarily doing it well. You’re doing it for no money. The transition to working with people who do this professionally, it felt like a breath of relief. To give trust to people you work with is such a huge, huge relief. I don’t take that for granted. To be able to sit back and chime in when I need to is a great thrill.” Rae also noted that Matsoukas and Penny rose up through the industry ranks and the strength their diverse backgrounds lends to the show, “Melina directed music videos, Prentice started as a writer trainee, he came up in the system, and me, coming from the internet, we had no ego about it. We just wanted to make the best show possible.”

From the amount of questions posed by young black women during and after the FYC panel, it was clear Matsoukas and Rae are inspiring a new generation of female creative talent.

  1. A fan asked how the talented group sets and resets their goals as they achieve success. Melina Matsoukas offered, “Stay humble. Continue to learn. Keep growing.” Prentice Penny had perspective as the most senior member of the company, “In Hollywood, there are degrees of making it. Now I want to dictate what I do. What else is interesting to me as a person?” Jay Ellis was appreciative, “Growth, learning and soaking in what’s around you.” Yvonne Orji summed it up, “Anything not growing is dying. My capacity to dream beyond me is now my goal. How can I help someone else? The goal is to continue to create.”
  2. What’s in store for season two of the comedy? While no spoilers were revealed, the executive producers teased that the new season is about forward motion. Penny noted, “Issa becomes less passively-aggressive over season one.” Rae added, “From the pilot to the end of the first season, Issa’s blossomed and become a different person. We like to see these people change. We want to see a progression.”

Season two of Insecure premieres July 23rd on HBO. 

In Prep For Season 2, ‘Insecure’ Cast & Creatives Talk Favorite Moments