‘Insecure’ showrunner Prentice Penny on why diverse writers’ rooms are key and what to expect in season 2

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Issa at We Got Y'all School Presentation Insecure

“Showrunners” is a new podcast from INSIDER — a series where we interview the people responsible for bringing TV shows to life.

The following is a transcript from our interview with Prentice Penny, the showrunner of HBO’s “Insecure.”

Subscribe to “Showrunners” on iTunes here, and listen to the episode to hear the highlights from our interview, and keep reading below for the full conversation.

Prentice Penny on growing up in Los Angeles 

INSIDER: The first thing I really want to know is the story of Prentice.

Penny: Oh, how far back were we trying to go?

INSIDER: Let’s go all the way back.

Penny: I grew up in [Los Angeles, California], and I grew up in the late ’70s or early ’80s, and I was [an] only child. I grew up where there were a hell of a lot of old grandparents, not like grandparents now who are on Facebook and who exercise. These are like old civil-rights [era] grandparents, like real grandparents. They weren’t warm and fuzzy. They were loving, but again not like grandparents today.

Prentice Penny TruTV

When my parents divorced, my dad was in the Air Force and so he moved back to Iowa where he was stationed. My mom was a paralegal who had just started law school at night. I spent a lot of time just with my grandparents. I’m an only child, so I spent a lot of time watching TV shows, or trying to entertain myself. Again, this is pre-video gaming. If you had a video game, it was like the Atari. It wasn’t like tablets now. I had to either draw or write or entertain myself. I [began] entertaining myself by writing or making up stories or things like that, and that’s how I think a lot of that all came to be. I was an only child, loved to write, loved to create, was into TV, and it just all eventually became that.

INSIDER: What were some of your favorite TV shows back then?

Penny: Growing up, I loved family shows, because I would bounce around a lot, like a lot of divorced kids. You spend part of Thanksgiving with your mom and then part with your dad, and then part with the cousins, you know what I mean? It was a very sectionalized kind of growing up, at least certainly on big occasions like that.

So I loved “Family Ties” or “Diff’rent Strokes” or “Facts of Life.” Anything where it felt like a problem was solved in 20 minutes. All that stuff just felt fun and great, so those were the shows like “Growing Pains,” “Love Boat,” all those old, old, old shows.

INSIDER: At what point did it click for you that this could be turned into a career?

Penny: It’s funny, because again it wasn’t like now where you’re aware of the term “showrunner.” Back then, you watched their shows, but you didn’t actually know what like Aaron Spelling did. You would just see his name, or you’d see these names on the end of like “Three’s Company” and they were like, “Oh, those were showrunners.” I just didn’t know what they were called.

For me growing up, and certainly as a person of color, Spike Lee was the first person — at least when I was in middle school and high school — that I became aware of [showrunners] and thought “Oh, this exists, and there’s somebody who looks like me who’s actually doing it.”

I think around ninth or tenth grade, when “She’s Gotta Have It” and “School Daze” came out, he used to do these books where he would [write] a journal of his “making of the movie,” and he would journal from the moment he came up with the idea, to the writing process and the filming, and then he’d put in the script along with stills from the production […] When I got to see it in his book, and hear him talking about taking meetings with heads of studios, it just became more galvanized like this is actually a real thing that I could probably really achieve or really do. Nobody in my family or my world did anything like that.

I really was talking about doing something that nobody in my family could understand, but I come from a family of […] people who are like, “I don’t need other people to make my stuff happen.” They were all self-made people. I think that part of the family helped me do something that again, that I probably, if I hadn’t seen Spike or people like that, I don’t know if I would have done it, or thought I could do [it].

INSIDER: It’s interesting that you say people probably didn’t even know what a showrunner was, let alone what they did, because I think that’s still somewhat the case now, although it’s changing.

Penny: Sure.

INSIDER: The landscape of television is shifting, and it feels more like people are paying attention to showrunners, as if they’re like movie directors.

Penny: Yeah, that is the closest thing. I think in the way that the director is revered in movies, the showrunner is revered in TV. Whereas a TV director will sort of come in and maybe do one, two, or three [episodes], they’re kind of like mercenaries. They’re there and then they’re gone, whereas the showrunner is not just conceiving this episode, but they’re saying, “How does this series work for all 8, 10, 12, or 22 episodes? What arcs are we telling?”

[Showrunners] almost become like, in the way you have Native American traditions where there are storytellers who are not just painting a one-off, they’re creating a world. Sometimes [a showrunner] isn’t necessarily the person coming up with the idea, but certainly they’re hiring the writing staff and running the writers room and figuring out, what stories are we telling, and what the arcs are, and approving outlines, approving scripts, in charge of re-writing, casting, music. From the very beginning to the end, you’re the person steering the ship. That’s very similar to what a director does in movies.

Issa at school Insecure

What being a showrunner for “Insecure” means

INSIDER: What is your day-to-day operations like as a showrunner for “Insecure”?

Penny: The show “Insecure” is based off Issa Rae’s web series [“Awkward Black Girl”] that is awesome, and so she’s obviously the whole reason why we’re here. Our relationship is very special, I think. We have a very unique relationship in that I think we both have a lot of respect for each other. She allows me to do my job as a showrunner, but I also never lose sight of the fact that the show always has to be told through her lens.

The writers often joke in a room that we’re “mom” and “dad,” and neither one of us makes a decision without talking to the other. I would say 90% of the time we’re pretty aligned in how we want to do the show, but then the 10% of times we just talk it out: “I’m thinking this, why are you thinking this?” and then we figure out what’s best for the show.

I think we have a very unique relationship from how we assemble the writers’ room, to all those things, the entire process. We work hand-in-hand in creating a lot of those things, but she’s always very respectful, and I try to obviously always be very respectful in the same way.

INSIDER: So how do you two work together to build your team? What kinds of people are you looking for when you’re hiring for the writers’ room?

Penny: We were very blessed — we brought back every single writer that we had in the first season to the second season, and we hired two new writers. I think our vision in the beginning when we were first assembling our staff was that the show is a comedy, so we know we needed comedic people, but the show has a lot of drama as well, so we knew we wanted a combination of comedic writers and we wanted some drama writers.

What I have found is, especially being a writer of color, I feel like a lot of times I’ve been on a staff where I’m the only person who looks like me. You might have six or seven guys, and it’s no knock on people that went to Harvard, but you’re like, “There’s six or seven guys who all went to Harvard.” They’re amazing and talented and funny, but there’s not six or seven people who look like me.

Sometimes in a writers’ room, voices can be repeated. For us it was, “how do we make sure that we don’t have a repeat voice in the room? We don’t need another Issa in the room.” You know what I mean? It’s like, we have Issa. We don’t need another me. We have a me. So how do we find six other people to be different, and bring a different voice and energy?

It was very purposeful. I knew from my experience that I didn’t want to repeat people. I didn’t want to repeat a sense of humor or a POV, because we wanted every person in the room to feel unique.

Writers’ rooms are tough. You run the danger of them becoming echo chambers of their own thoughts, and similar personalities. That’s death to me. The way to always keep it fresh is to always introduce new things, new elements, so people don’t feel repetitive.

Issa and Molly at Taco Truck Insecure

Obviously the show is about an African-American woman, so we knew we wanted those voices. We also wanted different ages of African-American women, and different sexual preferences of women and men. Again I’m very aware, as a person of color, of making sure that people feel represented in the room, but certainly that things feel fresh and interesting.

We have single people, married people, people with kids, people not with kids. Our room has, I think, four gay and lesbian writers. We have two drama writers, six comedy writers, people who have various dark sensibilities, people who can tell really sweet stories, people who also give you a thing that turns a story on its head in a different way.

INSIDER: You’re from LA, and the show is obviously based in LA, and I feel like LA is such a character in the show itself, but do any non-LA writers ever say, “Oh, this is way too inside, I’m not understanding because I’m not from here”?

Penny: I think sometimes when you’re on network TV, the tendency is to go broad and make sure everybody understands. HBO’s the opposite. They’re saying “be uber-specific to a point where people are either going to get it, or if not, they’ll look it up or they’ll ask somebody,” which also promotes conversation.

Issa and I are both from LA When we connected, we both realized that we grew up a block over from each other, which we didn’t know. I went to school with her brothers. We went to the same elementary school. She’s always good to remind me that I’m 10 years older than her, so she wasn’t there when I was there, of course, but we certainly grew up in the same neighborhood in LA.

One of our writer’s assistants is from LA, but everybody else is from Savannah, Memphis, Kansas City, New York, Dallas, San Francisco, Chicago — all over the rest of the country.

I feel like you see a very specific LA on TV, right? At least for sure with HBO you see “Entourage,” which is a very specific LA and a very specific world. They’re movie stars, so they’re up in the Hills and in Malibu and all these amazing places. Then when you see people of color, and this is no knock, it’s like they’re in “Straight Outta Compton,” or they’re in “Boyz in the Hood.” It paints a very different LA.

Issa and I grew up in an LA that’s neither one of those things, but has its own beauty and life that exists there, too.

Prentice Penny and Issa Rae onstage HBO Insecure

For us it was like, how do we show the Windsor Hill/View Park/Inglewood area [in a way] that seems beautiful and amazing, and becomes a character in the same way that Malibu and Compton and those neighborhoods become like a character?

How do we paint where we grew up as beautiful and amazing, and we don’t necessarily have to have a beach or a mansion to show the beauty and the smallness of our neighborhood. I think in the same way with how Woody Allen shows New York, or Spike shows Brooklyn, it’s like for us it was “how do we make this neighborhood that people think they know?” 

INSIDER: You guys did that with the fundraiser that Issa’s character organizes. She specifically says to the room full of white people, “We can take them to a neighborhood that’s close by, and that has these beautiful things.”

Penny: Yeah and it’s five minutes from them, and looks amazing and beautiful and full of people of color who are doing well, who look like them. It’s funny, because the LA Times just wrote an article about how gentrified that neighborhood is becoming, and it is. It used to be all white people, and then they left, and then they moved back because it’s like, “These are nice houses, at half the price of the houses in Beverly Hills, and it’s the same architect.”

How Penny met “Insecure” star Issa Rae

INSIDER: Just to backtrack a little bit, I want to hear the story of how you came to be the showrunner for “Insecure.” 

Penny: So I was on “Brooklyn 99” at the time. I think I was in my second year there, and I saw that [“Insecure”] was being picked up as a pilot and that Larry Wilmore couldn’t do it because he had to do “The Nightly Show” for Comedy Central.

I knew who Issa was — I was a fan of hers. My mom had told me about Issa like a year or two before. She was like, “Baby, there’s a woman in the neighborhood doing a web series.” You know how like your mom calls and says all that stuff?

I knew who she was, and I knew that the show was at HBO, but I didn’t know where it stood, because it had been there for like two years at that point. I was ready to be a showrunner. I just remember, I had a very cushy position for sure, and I reached out to my agent. I was like, “Yo, get me a meeting on this show. This show is too important, it’s too special. These opportunities don’t come across every day. They don’t happen every day.”

Another agent at the agency went to college with Issa, so they were friends. Her name was Ashley, and so Ashley was like “Reach out to her. Why don’t you write her a letter?” It seemed like a very old-school thing to do, but I wrote her a letter, because I read the script and loved it.

I had worked at a nonprofit before I was a writer. I’ve had situations where somebody, literally in the writers’ room, had asked me what “on fleek” means. I’ve had these [same] moments. If you’re a person of color, you have these moments where people ask you to explain things as if you’re the arbiter of everything African-American, or any person of color. It’s just like a script that anybody can, on a human level, connect to. We’re all insecure about something. We all have our issues, our hang-ups.

So obviously I had had similar experiences to her in the real world, and so I wrote her a letter. I remember, I went to a book signing for her, and I just sat outside. I was talking to other people, and then she just came outside, and we talked for like maybe 10 minutes, and that’s being generous, but we just hit it off.

I figured we would have a follow-up meeting, to actually talk more formally, but they were like, “Yeah, she thinks you’re cool. Let’s do it.”

Issa and Molly Insecure

How music selection can make or break a scene

INSIDER: Another one of my favorite things about “Insecure” is how the music does a great job of characterizing LA and introducing certain tones or emotions. How involved are you with music selection?

Penny: First off, we have amazing people on the music side. Kier Lehman is our music supervisor, who has found amazing music for the show. Solange Knowles was our musical [consultant]. It’s funny, because she was working on [her album] “A Seat at the Table” at the same time, and she was telling us about tracks, and you’re just like, “Oh, that sounds dope.” Then when it comes out and it just hits you’re like, “Oh snap, that’s what she was talking about.”

She and Raphael Saadiq from the group Tony!Toni!Toné! and all his amazingness, does the music.

We have such a good group of people who are working on the music, so it’s almost like a wealth of riches. Our house director, Melina Matsoukas, has an amazing ear, and Issa has an awesome ear for music. Melina will edit the show and then just take a day to play with music.

INSIDER: Has there ever been a song that you guys really wanted to use for something that you couldn’t?

Penny: There’s always money issues, right? Like last year we would have to rob from Peter to pay Paul a little bit. But HBO would say “no, let’s find some extra money.”

Really, the Kendrick Lamar song was the song that we had put in initially [in the pilot]. It hadn’t quite hit yet but then it hit and it was like “Oof, that cost just went up.”

Then we thought maybe we should find another song, because then it [had been] out for a while. We watched it with other music, and thought “maybe we’ll go with some Snoop” because that’s very west coast, but no matter what we put in there, nothing felt LA like Kendrick in that moment. We said “let’s just pony up the money for Kendrick” and it just was perfect.

Issa at beach clean up Insecure

That’s one thing that I’ve learned, especially from HBO, is every show has a budget, right? You have to play within the rules that you have to play in, but [showrunning is] also about not compromising sometimes, and taking your shots when you feel like, “I have to take this shot here. We have to, there’s something special about it.”

That’s what TV to me is about — it’s about moments. I don’t necessarily remember the funniest joke in “The Cosby Show” or the funniest joke on “Friends,” but I think people remember moments. You remember when Ross kissed Rachel, or you remember the moment when the Cosby family sang Ray Charles, or like on “The Office” when Jim and Pam finally get together. You know these moments, right? That’s what sticks with people. I think that’s why people love TV — you get these moments with these people you fall in love with over and over and over again.

It’s about those moments, and never losing sight of that. Even in the wake of all the other production things you have to deal with, never forget that these things are about other human beings having connections with other human people.

Penny’s favorite moments from season one of “Insecure”

INSIDER: Yeah, and especially because “Insecure” is so rooted in the idea of relationships and friendships and romance. What are some of the moments that you were the most proud of from season one, that you felt would really stick with audiences?

Penny: You read moments in scripts, but then they have to actually play out in real time. For me, the moments I love in the show are like when I read the script, the pilot, and the moment when Issa mentions the “broken p—y” — she makes a joke to make Molly feel better.

What’s great about that isn’t the “broken p—-y” — what’s great at that moment is it’s a very human thing, a friend trying to cheer up another friend, right? It didn’t matter what the words were, it’s like this is a moment that we’ve all been to, where we see a friend of ours is hurting, and we’re trying to make that friend feel better.

<img src="http://static1.thisisinsider.com/image/591f5f571cc9c507398b4602-1800/issa%20and%20molly%
Source: http://www.thisisinsider.com/insecure-prentice-penny-showrunner-podcast-2017-5

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