Interview with Prentice Penny, Showrunner of HBO’s ‘Insecure’

Prentice Penny talks about making HBO’s great new comedy Insecure

Olivia Pope. Annalise Keating. Cookie Lyon. One thing each of these black leading ladies on television has in common is their strength. But when creator, co-writer, and star of HBO’s Insecure, Issa Rae, initially pitched her show to HBO, she told producers, “I’m not a strong black woman; I’m a weak black woman.”

“Typically on TV, the images of black women in narratives are those that are super put-together or that ‘slay’,” said Prentice Penny, showrunner of Insecure. “There’s this idea that black women can’t be as insecure as white women or any other women. What’s beautiful about our show is just seeing black women as people.”

prentice penny
(Photo: HBO)

Insecure follows the career and romance struggles of Issa (Issa Rae), a woman who works for a nonprofit in Los Angeles, and her best friend Molly (Yvonne Orji), a corporate lawyer. “I think at the core of their friendship is that they’re just so real to each other. They’re truly supportive and accept each other for who they are. They have opinions about how each other lives, but they’re never judgmental opinions. They have each other’s best interests at heart.”

A female narrative about friendship? HBO has certainly done this before, with Sex and the City and Girls, but Insecure ushers in a fresh era of female friendship on television and even dismantles the four-girl formula. Although this wasn’t intentional. In the writers’ room, very few discussions came up about the show’s possible relationship to Girls.

“Obviously you can draw comparisons between Issa and Lena [Dunham], both being writer-performers,” said Penny. “But in terms of the story we are telling, our show is very different tonally. We knew we were just going to be our own thing and that would be enough.”

Another change of tone is how truly real this show feels. You won’t find bonding over Jimmy Choos, something Rae, Penny, and the writers were very cognizant of.

“Issa works for nonprofit, so there’s a certain income level she exists in. Plus, her boyfriend is not working, has been on unemployment for a while. With Molly, we wanted her to be the type of person who lives a better life on paper than she does in real life. She wants her life to look like a catalog. We were always trying to anchor the show in finding the reality of people like this.”

Issa also has a rapping quirk that she uses to pump herself up during insecure moments. In the pilot, she actually ends up taking her act on stage for a very candid performance that ends up on YouTube, a medium Rae, herself, is no stranger to. She’s best-known for her YouTube web series Awkward Black Girlwhich has more than 200,000 subscribers. Based on this series, she released a book in 2015 called The Misadventures of Awkward Black Girl.

“I had read articles about Issa before I had seen her web series. I think my mom had forwarded me some information because Issa and I are both from the same neighborhood,” said Penny with a laugh. “You know, your mom always gives you stuff like that.”

prentice penny
(Photo: HBO)

When Penny saw that HBO would pick up Rae’s pilot, he knew he had to be part of this adventure. “I just know opportunities like that are so rare for people of color. I thought I could be helpful. I knew I wanted to be showrunner, so I kind of just went after it and got it.”

Prentice Penny’s resume contains varied and layered work on such shows as FOX’s Brooklyn Nine-Nine to NBC’s Scrubs to the UPN classic Girlfriends. He adds many different projects under his belt to give him more opportunities. “As a writer of color, you can get pigeon-holed. Really any writer in Hollywood can get pigeon-holed. I want to make sure stuff I work on feels different.”

Yet, for as different as each project is, each shares the commonality of representing the unheard. The funny side to life in a hospital. What it’s like to be a black, gay cop. Four black women facing life’s challenges together. When choosing projects, Penny often asks himself whether he’ll ever get another chance to do something like it.

“Things you don’t get to do every day,” he said. “That’s what I gravitate toward.”

Insecure is not a show, or narrative, you see on TV every day. And that’s what Prentice Penny and HBO are counting on.

Insecure premieres on HBO on Sunday, October 9 at 10:30 p.m. EST. The pilot episode is available for streaming now on HBO GO and HBO NOW.

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