‘Insecure’ Showrunner Prentice Penny Is Ready to Move On

Before Insecure launched in 2016, showrunner Prentice Penny likes to say that he was in the “outgoing call business.” Five years and as many seasons later, the longtime comedy writer with credits on Scrubs, Happy Endings and Brooklyn Nine-Nine finally finds himself firmly in the “incoming call” one.

Now, with the Emmy-winning HBO comedy created by and starring Issa Rae set to end, the 48-year-old producer is focused on what he wants to say when that phone rings. Already, the South L.A. native who got his start on 2000’s Girlfriends has written and directed his first feature (Netflix’s Uncorked), explored his love of finer things as host of late TruTV docuseries Upscale and, as of August, signed a new deal with Disney’s new POC-focused content brand Onyx Collective.

There, if all goes according to plan, the married father of three will finally have a show to call his own. “We came in with a slate of 12 projects, and I’m writing and directing three or four of them,” says Penny. “Insecure made TV feel fun again for me. I want to keep chasing that feeling.”

You’ve spent five years on a show with a very female POV. What have you learned about women?

I also worked on Girlfriends, so more than half of my career has been spent in writers rooms with Black women. When I first started on Girlfriends, I was only married for, like, nine months. I’ve been married 18 years now. What I’ve learned most is how to be a better listener, for sure, and to listen for what’s not necessarily being said. My wife would probably say I have a long way to go.

How was your time on Girlfriends as first Hollywood jobs go?

I didn’t go to an HBCU, so Girlfriends felt like that for me. Mara [Brock Akil] treated everybody, whether they were a co-EP or a staff writer, the same. I would say 80 percent of the things I do, I learned from Mara … just by proxy of that being my first show. It’s like how your parents are your introduction to how people act. If they’re super dysfunctional, you’re either repelled by that or you replicate it down the line.

Your mother, Brenda Penny, is the Superior Court judge in Britney Spears’ conservatorship hearings — which prompted a lot of vitriol aimed at you on Twitter from some of the “Free Britney” crowd.

It’s chilled out a lot, but it was frequent when there were big developments. Now that [the case] is moving in a favorable way for [Spears], none of that happens.

Insecure was your first time showrunning, but it wasn’t your vision you were executing. How did that impact the job for you?

The second I got this job, I called [TV writer] Jonathan Groff. I watched him do the same thing on Happy Endings, nurturing [creator] David Caspe but never getting in the way of what he wanted to do. I tried to apply the same thing with Issa. As she started to figure out what she wanted to do, I could step back and help out in other areas. Because she can’t do everything. She’s in 90 percent of the scenes.

What’s changed the most for your career since taking this job?

Before Insecure, I had been working on a lot of network shows. I missed working with Black people. I was the only one in those rooms, which wasn’t always comfortable — not uncomfortable but isolating at a certain point. Also, when I came into this show, I was in the outgoing call business. Leaving this show, it’s more an incoming call business. (Laughs.) So if the power’s shifting and I get creative control, I have to ask myself, “What are the things that matter to me?”

So, what matters to you?

I want to do more. HBO is awesome, but there’s a limited amount of programming they can do based on their structure. I want to get into animation, do some other docuseries, maybe family stuff … telling stories, not just relegated to people of color but telling stories that matter in some way. I never want to have to justify why I want to make something. I want some understanding, at a base level, of what matters and why that matters. And with Onyx, we can sell to a ton of places — whether it’s Hulu, FX, ABC, ESPN or Disney+.

The last time we spoke, you said you felt conflicted about Insecure getting its first best comedy nomination at the Emmys amid the social unrest of 2020. How do you feel about it a year later?

First, I’m happy to be a part of anything that’s moving culture. But I never want Issa to have to apologize for me or anything I say. So, when the Emmy stuff happened, I had a lot of strong feelings — but I wasn’t trying to get in the way of her moment. And even though they opened more slots for shows of color, I was like, “There’s a systemic problem here that nobody really wants to dive into.” I never understood how we could win a Peabody Award but the guild never nominates us for Writers Guild Awards.

Is it an exposure issue?

Every network wants to win, so they’re putting their marketing dollars toward shows they think can win. Because the voters watch where the marketing dollars go, the voters or the critics talk about those shows. Then the network goes, “That’s what they’re talking about. Let’s keep funneling our budget there.” It’s a loop that nobody will get off. It’s not parity. So how can a show that’s not getting seen get seen?

You’re a WGA member and a TV Academy voter. What would you like to see happen to make those shows get seen by more people?

There are ways that you could legislate certain things. When we got nominated [for an Emmy], it would’ve been a perfect time for the Academy to go, “Hey, now that we have more than five nominated series, these other two or three slots are going to go to the highest-rated shows of color from now on. We’re not letting another majority white show in after our five.” Then critics [and voters] would have to watch those shows, but that’s not what happened.

It’s early for legacy talk, but how would you like Insecure to be remembered?

We’ve got to open doors and tell our stories, unapologetically, by us and for us in a way that wasn’t trying to make it be palatable for other people. I wanted to leave the talent pool of writers, the cast and directors better than how I found it. In terms of the mainstream culture, I hope people can see that art by people of color can also exist at a very high level without needing to be about our pain. Because when I get pitched, “This is about this so-and-so slave that went through … ” I don’t want to write that. I don’t want to get relegated to that — basketball and rap being all that Black people have to contribute to the culture.

What’s the last thing that made you laugh?

I was just rewatching Eastbound & Down, and it’s insane what they did. Danny McBride does what makes him and his boys in North Carolina laugh. That’s the best place to make the comedy from. Smart people in comedy, Norman Lear or Mel Brooks, they do what makes them laugh. When you start messing with your compass, that’s the bad place. It’s like when Tobey Maguire was Venom. Don’t start dancing like that. That’s weird, bro. Just be Spider-Man.

Interview edited for length and clarity.

This story first appeared in the Nov. 10 issue of The Hollywood Reporter magazine. Click here to subscribe.