'Insecure' show runner on five years of growth (and more)

Welcome to Thanks, I Love It, our series highlighting something onscreen we're obsessed with this week. 

The episode titles of HBO’s Insecure have always contained clues. 

They’re not hidden, either; Season 1’s episodes, starting with “Insecure as F**k” all end in that choice descriptor. Then it was “Hella,” “-Like,” “Lowkey,” and finally “Okay?!” The tone reflects Issa’s (Issa Rae) mental and emotional state from her 20s into her 30s, from being an adult on paper to someone with the career and relationships she always dreamed of. She hasn’t got it all figured out, but she’s miles from where she started.

“We always knew thematically what the ending was, which was that the show was about our character going from being uncomfortable, and being insecure in her insecurities to being secure in her insecurities,” showrunner Prentice Penny tells Mashable in a Zoom interview. “That they never leave, but that you've learned how to deal with them differently.”

Penny points out an almost universal struggle that Insecure’s characters know all too well; We set goals when we’re younger, benchmarks for where we want to be in life, and when we don’t hit them we feel like we’ve failed. Growing up is moving those goal posts and making peace with it.

“That's why the okays have a question mark,” he adds. “Because it's not about okay, period, because there is no okay, period, right? It's, ‘it's okay, I'm okay. Right now I'm okay, and it doesn’t mean I’ll always be okay.”

"The show was about our character going from being uncomfortable, and being insecure in her insecurities to being secure in her insecurities."

Season 4 dealt largely with the strained friendship between Issa and Molly (Yvonne Orji), but 5 quickly jumps ahead to a time when they’re good again. Playing with time is deliberate, Penny says, a conscious decision by the writers not to gloss over difficult chapters, but to pick out the moments that matter most. 

“It was really about just like, what are the moments we feel we need to see, what are the moments that really matter” he says. “When do we want time to slow down and feel [more] specific? 

The friends share a tense moment in Season 5, episode 1, when they’re cordial but still not back to their old dynamic. “Are we gonna be okay?” Molly asks Issa. There it is again, that tentative “okay?!” that threads through the season. 

“This season is really about getting Issa and Molly to a place where they're much more intentional about their friendship and more intentional about their dynamic and much more intentional about their love to each other,” Penny says. “And knowing that not everything is promised, not everything is perfect, and their friendship is just as fragile.”

Kelly (Natasha Rothwell), Molly (Yvonne Orji), and Issa (Issa Rae) have battled their insecurities for five seasons on "Insecure." Credit: HBO

Episode 2 jumps to a year later, no longer immersing us in the friends’ pain but skipping to a time when they’ve repaired the relationship. A similar jump occurs after episode 3, a character study of Issa’s ex Lawrence (Jay Ellis), who we leave at a critical juncture and won’t catch up with until later.

“We have the benefit of knowing why we did it this way,” Penny adds. “It's almost like WandaVision — it's like ‘I don't know why I'm watching the first two episodes,’ and as soon as you get to episode three or four you’re like ‘Oh, I get it now!’ And then you get to the end and you like it all makes sense.”

“There was a very easy space for this show to be super nuanced about the women and kind of treat the men just like pawns and move them around,” Penny says, reflecting on Lawrence in particular. “But what I love that Issa always allowed the space for was for the men to be their authentic selves too, and to see the ways that they're flawed and not perfect.”

Over five seasons, Lawrence has gone from what seemed like a textbook deadbeat boyfriend to finding his own path in his career and friendships, and his delicate relationship with Condola (Christina Elmore) and their newborn son.

Lawrence (Jay Ellis, left) has done a lot of growing up of his own since Season 1 of "Insecure." Credit: HBO

Penny has been with Insecure from the beginning, after being co-executive producer on Brooklyn Nine-Nine and feeling ready to branch out into his own projects. 

“I went to read the pilot and I was just blown away at how good it was, how real it was, how authentic — how it was saying all the things that I was feeling, my friends were feeling,” he says.

He found similarities with Rae, who is from the same neighborhood, with Issa the character and her work in nonprofit, and with the experience many shared of usually being the only person of color in a room full of white artists. 

“I just wanted to work on something cool,” he recalls. “I wanted to work with Black people — it wasn't that thought out. I read the script, I thought it was great. I was at a point where I was like, ‘I just want to do cool shit’ and this felt cool.”

Growth has been the name of the game in front of and behind the camera, where someone like Rae who had never hired directors or put together a writers room has now become a name synonymous with knocking both those tasks out of the park. Director Ava Berkofsky started as a cinematographer; Penny himself got his first chance at leading a show and made the jump to directing episodes as the series continued. 

“We all kind of felt like we were on our own little island,” Penny says. “We were kind of like the Island of Misfit Toys. We were just gonna come in here and do our own things — just make dope shit with dope people. And when you see dope people you're just like that can only yield something good or creative. So that's what I'm super proud of.” 

Insecure is now streaming on HBO and HBO Max, with new episodes every Sunday.