December 7, 2021

Prentice Penny Displays on the Finish of ‘Insecure,’ Spin-Off Discuss, and an Upcoming Western Episode

17 min read

Last Sunday, HBO’s hit dramedy Insecure started its ascension to TV’s candy hereafter. It’s been an extended journey from damaged pussies and freestyle rappin’ at Issa’s L.A. flat and these characters understand it. “What would you do in the event you knew every thing was coming to an finish?” Kelli (Natasha Rothwell) coos into her podcast microphone.

Earlier in its fifth season premiere, Kelli learns that the organizers of their Stanford alumni reunion have mistook her for useless, and whereas Kelli is often seen as a foil to the seriousness of her circle, she appeared to take it actually laborious. She contemplates her legacy—how she’s seen and the way she’s lived her life to this point. They’re large questions that the present’s been wrestling with for its complete celebrated run, however the showrunner’s hardly needed us to really feel like something is truly closing. What’s a finale however a second in time the place one chapter ends and one other begins?

Prentice Penny, who has served as producer, author and showrunner of Insecure, is sort of optimistic in regards to the present’s that means each inside and outdoors the tube. These kinds of conversations about the place a present will find yourself fascinate Penny up to a degree, however his is a extra sobering learn: “Our present is birthed out of reveals like Residing Single and Girlfriends. They’re enhances. They’re ancestors to this. So I’m excited to see what can be impressed by our present.”

Trying again on its run, Penny’s phrases spill, simply and lovingly, in regards to the lovely progress he’s seen in Kelli, Lawrence, and Molly. He was there on the Essence Competition all these years in the past when “folks might give a shit about what we had been doing,” and within the years after the place they may barely get via the door.

Penny comes bearing a robust TV portfolio with reveals like Scrubs, Brooklyn 9-9, and, sure, Girlfriends in his again pocket. These reveals, and their banter and fluidity, from the ridiculous to the heart-wrenching, outfitted the Los Angeles native with the nerve and acumen to tackle a manufacturing like Insecure. However that couldn’t put together him for the enjoyable of writing jokes with Natasha Rothwell (please chill on the spin-off discuss!), the evolution of Yvonne Orji right into a family title, or taking pictures a model new season throughout a worldwide pandemic. There have been joyous and troublesome classes discovered alongside the way in which—just like the interval between seasons 3 and 4 when each he and Issa took a break to work in movie—however every have imbued Penny with a deep sense of gratitude for his forged and the way far they’ve come. “They’re getting alternatives now that it took me longer to get to. I’m pleased they don’t have to attend as lengthy.”

This interview has been edited and condensed for readability.

How does it really feel to be accomplished with the sequence?

I’m tremendous excited for folks to look at the final season. We’ve been off, not fairly a yr however somewhat greater than that. I don’t know if it completely feels prefer it’s over but as a result of we simply began however every thing is in these bizarre steps. Like first, it’s ending writing, then ending wrapping, then airing. So I feel it’ll kick in after we get nearer to the time, however for proper now it’s undoubtedly pleasure.

The primary episode undoubtedly has audiences considering of the tip. Y’all killed off Kelli! She has that complete monologue on the finish. Like, what in the event you knew the tip was coming? It’s such a meta query.

[Laughs] Yeah, it’s tremendous meta on high of that as nicely.

Was {that a} acutely aware selection of letting the viewers know, hey, the characters kinda know that is it?

I don’t know if we had been excited about the viewers with that. It was extra like, ya know, the present is ending they usually’re additionally at an age the place… the present begins once they’re of their late twenties and the present is now turning to the place they’re coping with extra grownup selections. It sorta looks like your thirties set you up to your forties, and so forth and so forth. There’s a shift taking place of how they need themselves to be remembered and the place they’re rising to. I don’t suppose we had been that calculated however we had been excited about how the characters had been contemplating legacy.

The forged of Insecure go to Stanford in Season 5


Talking of legacy, the forged has been fairly outspoken in regards to the uniqueness of this present within the pantheon of Black TV and TV extra typically. In your estimation what units it aside from reveals like Residing Single or Girlfriends except for the HBO-ness of all of it?

They’re all simply completely different reveals, ya know? They’re reveals which have Black ladies on the core of their foremost characters and clearly these are two superb reveals—considered one of which I wrote on, Girlfriends. However when it comes to setting it aside, it’s kinda like, what units it aside from any present, not simply these particular reveals, you recognize what I imply? I used to be truly texting Mara [Brock Akil, creator of Girlfriends] yesterday simply how grateful I used to be. And the way working for Mara was a masterclass in simply easy methods to be an expert. I used to be telling her, “You had been doing issues that we do now however you had been doing it 14 years in the past.” I bear in mind her speaking about how she needed to make Girlfriends extra single camera-y within the moments that wanted to be extra dramatic than comedic. She was doing all of these issues the place now it’s simply how we make TV, however that wasn’t how we made TV in 2006. I feel our present is birthed out of reveals like Residing Single and Girlfriends. They’re enhances. They’re the ancestors to this. So I’m excited to see what can be impressed by our present.

It does really feel like this continuation. Residing Single was made for its time and Girlfriends was made for its time. Each of them are pushing issues ahead in their very own particular methods. And Insecure is of its time. Just like the millennial ladies and men on this social circle who’re studying easy methods to age and develop up collectively. There’s an underlying theme throughout the first couple episodes the place it’s like, when do these folks determine it out? And the reply is, you don’t! [Laughs]

Yeah! That was all the time a giant driver for us. Thematically, the characters’ arc from the primary episode to the final—Issa wanted to learn to be safe in her insecurities. To know that they by no means depart you, simply study to handle them in a more healthy, higher approach. You simply perceive that that’s all a part of it. There’s no, “Oh, I conquered it.” We’ll by no means conquer it. You simply discover methods to develop and thrive it doesn’t matter what insecurities you might need. However yeah that’s the purpose, ya know? That’s what dwelling is. You study these classes alongside the way in which. It by no means stops or goes away.

There isn’t a figuring-out level however there are moments in a single’s life that modifications them. And it’s like, how are you going to reply to this? This season, particularly for Lawrence, he’s beginning a brand new chapter. The place as soon as he could possibly be a single dude hoeing round, now he has a child. He desires to be part of that baby’s life. It looks as if that is the primary time the characters are coping with child mama/daddy drama. How do you suppose the present skirts that line of displaying the true problem of other parenting setups between Lawrence and Condola?

One factor that we needed to point out was that Lawrence didn’t plan on this; he didn’t rely on this being part of his life. And what we needed all our characters, even Issa, to confront was like, what occurs if you get dealt a hand that you just didn’t anticipate to play? Do you fold? Do you attempt to make one of the best of that hand? For Lawrence, he didn’t rely on this. He had a complete plan of probably being with Issa and having a job in San Francisco. So, what occurs when somebody comes alongside and disrupts that? Do you step up? Do you blame others? Do you might have plenty of anger and frustration? Identical factor for Condola. She tried to play this robust “I don’t want you” function, and we needed to check that. We needed to point out up trustworthy and actual for 2 individuals who didn’t anticipate their lives to finish up this manner.

Are you able to recall how the writing and manufacturing staff approached season 4? It actually appeared like a turning level within the present. It simply appeared like y’all began hitting on all of the issues that made Insecure actually fucking cool. Centering Issa and Molly’s friendship breakup, it’s not one thing that typically occurs on TV. And in addition the cinematography. Y’all simply stepped it up.

Yeah, plenty of issues occurred that yr. The primary factor is we put Issa and Molly’s real love story on the heart of the present. Essentially, these two ladies we beloved, we acquired to see an actual story round with out having males be the motive force of the story. It was an enormous factor for us to care about otherwise than who they had been gonna be with. It’s in regards to the love story in peril, so it modified issues. That season, Shiona Turini, our costume designer, got here in midway via season 3. She acquired to be there for a full season and set completely different seems. That was a time that Issa and I took a break from the present to make films. We each got here again renewed.

And from a directing standpoint, I grew rather a lot directing a function [Uncorked], and I needed to carry extra cinematography, extra issues we don’t usually do in our present like taking pictures in silhouette or in slow-motion. Taking pictures in a single take with out slicing. And even being a greater director telling tales. Usually, that final scene [in season 4] with Issa, Lawrence and Condola, we would’ve made the Condola scene one lengthy flashback. I used to be pitching it as we must always minimize forwards and backwards so it could appear to be one dialog. As a result of visually that could possibly be actually fascinating, and one another solutions the opposite’s questions and we don’t actually know the place we’re at till we’re in it. The viewers received’t know if you’re slicing out of one thing so we might use that for influence. However I don’t know if I’d’ve considered that with out directing a film.

That was a time that Issa and I took a break from the present to make films. We each got here again renewed.

Yeah, it looks as if there’s this nice mixture of continuity and these bursts of recent folks, new concepts. I bear in mind watching that season and simply being like, oh, y’all have figured it the fuck out fully. Only a whole cinematic expertise. The film that you just’re speaking about, although, that’s Uncorked, proper? Have been you simply selecting up suggestions from [cinematographer] Elliot Davis or [editor] Sandra [Montiel]?

I had labored with Sandra on Completely happy Endings and Brooklyn 9-9 and he or she’s such an superior editor. However undoubtedly I discovered a ton from Elliot Davis, how might you not? The man has forgotten extra about films than any of us will ever study. Like, he was the primary AC on the primary Soiled Harry film. Shot Out Of Sight. The man is superb. He all the time inspired me. On daily basis we’d sit in a restaurant and discuss in regards to the script, discuss methods to visually push the imagery. We’d discuss what the characters are feeling. We’d discuss films like Final Tango in Paris after which use these as reference factors, whereas sometimes on a TV present you don’t have the time to try this. And the present is already set, the look of the present. You may play somewhat bit however nonetheless should honor what got here earlier than it. In a film, nothing existed earlier than or after this so it may be no matter it must be. That’s the distinction; that’s the enjoyable half. I discovered a lot from Elliot I needed to carry again to the present to assist how we instructed tales visually. This season too, like thematically, I’d watch different films to assist. Like one episode, I really feel, is a Western.


Yeah, you’ll see when it comes out later. I watched plenty of John Ford, plenty of Excessive Midday and Fistful of {Dollars} as a result of thematically, that’s what was taking place. So I needed to lean into that really feel. We shot it rather a lot like a Western.

That’s actually fascinating.

You don’t watch Insecure considering Western! When that episode airs there are plenty of issues which are Western-y about it.

I watched plenty of John Ford, plenty of Excessive Midday and Fistful of {Dollars} as a result of thematically, that’s what was taking place. So I needed to lean into that really feel. We shot it rather a lot like a Western.

So, simply coming again to the primary episode, first off, RIP Kelli. For them to come back collectively and for Issa and Molly to reunite and to sorta work up on their friendship, what was the selection behind that? As a result of it actually might’ve gone both approach.

We did wish to honor the truth that they wouldn’t be absolutely collectively simply because they talked somewhat bit. It’s like a damaged bone—it takes a while to heal. Within the writers’ room we used the analogy of an athlete breaking a bone they usually haven’t examined it shortly, [so] they needed to come out of the sport. And they also’re nervous about coming again in and doing that transfer. They’re nervous their knee received’t maintain up the identical if it will get hit or no matter. And it’s not till you get your first shot, or dunk, or sort out to know, like, hey, my leg’s okay. We all the time measure whether or not Issa and Molly are okay primarily based on the hijinks they get into, whether or not it’s damaged pussy or the “wine down” fireplace or the Lyft battle or at Coachella being excessive. There’s all the time some kind of loopy factor they should undergo collectively that they will look again and chuckle about. They aren’t actually proper till they will crack jokes on one another with out worrying, Did I offend you? That’s the entire season, them discovering their approach again, recognizing that their relationship is fragile—and what I imply by that’s that, similar to some other relationship, it may be broken in the event you don’t nurture it. They thought that their friendship would simply final with out considering, no, now we have to be intentional. Now we have to place in actual work on this relationship. However that’s one thing you study as you get older too. Hey, I’ve to be intentional or it could not survive.

I used to be additionally excited about Kelli. Whereas I feel the Kelli of season 1 may’ve been in a position to chuckle off Stanford killing her, it does appear to be it takes an actual toll on her. It’s a kind of meta issues as a result of viewers are like, Kelli is so enjoyable, she deserves her personal spin-off. However then the Kelli throughout the present is reckoning with being a facet character. What was behind that selection?

Folks hold asking if she’s gonna get a spin-off. I hold telling folks Natasha is at Disney now. [Laughs]

Issa Rae in Insecure Season 5


Yo! She’s not checkin’ for no spin-off! [Laughs]

Figuring out Natasha, she has so many different issues she desires to do. I feel she loves enjoying Kelli; she’s doing films and White Lotus now. She’s doing superb. It’s an actual testomony to her wanting that as a result of her performances are all nice. Within the room she all the time offers us a ton of comedy to make use of for the present. However over time you don’t wanna simply be that. I feel it’s completely different if you’re the one controlling the joke. I feel that’s what occurred. Once more, it’s about legacy. She was questioning, is that this how folks actually see me? A reunion is an efficient time to get a way of the way you’re seen. It was solely the second time we acquired to rock Kelli—the primary being when Tiffany left her off the infant stuff. We needed to offer Kelli a journey that would take us via the entire season even when she doesn’t get a complete episode. This arc will proceed to play out right through to the tip. It’s good to see her journey and to offer her actual stuff.

Along with the casting of Black actors, it appeared to me that persons are responding to the leads of the present being dark-skinned ladies. Issa and Yvonne are each supremely gifted however was it important to you, possibly after the actual fact, that darkish pores and skin was not solely getting nice lighting, like hiya, but additionally such a large response?

That was our intention—to forged a dark-skinned Black girl as Molly. From the start. In actual life, Issa’s pal who Molly relies on is dark-skinned. That was all the time the objective; all the time the plan. Props to Issa as a result of her level was you by no means see two dark-skinned Black ladies in these roles which are the core of the relationships. You may see the Issa character with pure hair however the Molly character is perhaps the fairer one. And the second she mentioned it, I used to be like yeah precisely, ya know? It wasn’t even a doubt or a query. I’m glad that folks find it irresistible too.

How’s it been watching Issa and Yvonne and all these of us develop over time?

In some methods Issa and I are like large brother/lil sister. However in different methods I really feel very parental about them. Even once I first met Issa, I knew she was going to take over the world sooner or later. Similar to listening to her goals and targets. And I’m a dreams-and-goals particular person, however she even acquired me beat. So seeing her do it’s not tremendous stunning for her personal stuff. What I really like is how she acquired to be embraced as a dark-skinned Black girl cowl lady. The truth that she acquired to be the voice of the NBA final season. I feel Yvonne, much more so, nobody knew who she was. I bear in mind strolling down via the Essence Competition, we had been displaying the pilot, and folks might give a shit who we had been. [Laughs] No one knew what we had been doin’, why we had been there. Then three hundred and sixty five days later, we couldn’t stroll wherever. The screenings had been bought out. We needed to be ushered off via the pageant; it was a madhouse. To go from nobody is aware of who we’re to folks screaming, Lawrence! Molly! I’m tremendous pleased with all of them and their exterior endeavors too. Everyone’s doing stuff that has nothing to do with them being actors. They’re getting alternatives now that it took me rather a lot longer to get to. So I’m pleased now that they don’t have to attend as lengthy.

How was it watching Keke Palmer slide into her function as Condola’s sister? Did it come about as simply as her sending a tweet, forreal?

It was actually precisely what Keke mentioned: her sending a tweet and us saying to Vickie Thomas and her staff, yo is that this actual? So we referred to as they usually had been like, nah it’s actual! It was humorous that she ended up enjoying Condola’s sister since most of her shade on the present was about Condola. And she or he was like, I didn’t shade you I simply hated the scenario. [Laughs] It’s so loopy as a result of they’re nice collectively, as you’ll see. Keke is simply superior.

Wade Allain-Marcus, Jean Elie, Leonard Robinson, Yvonne Orji, Issa Rae, Christina Elmore, Jay Ellis, Prentice Penny, and Courtney Taylor attend the after get together for the premiere of HBO’s Insecure Season 5 on October 21, 2021, in Los Angeles, California.

Amy Sussman/Getty

There’s been a wholesome dose of drama exterior the purview of the present itself. How does the squad preserve focus within the midst of every thing?

Inner stuff—we haven’t had something on our facet. Nothing that I’ve seen. On the planet of constructing a present throughout COVID, it was tremendous troublesome. The start half was robust since you’re used to strolling as much as actors and having conversations. You couldn’t transfer the way you moved to start with. Like to offer a notice, we’d have to attend and clear issues. The method was simply extra of a grind. However when you begin doing the scenes, then you definately’re simply doing the work. That was the reprieve from it. We needed to finish the season with administrators that we referred to as our faves—not that we didn’t love all our administrators. We love Melina [Matsoukas], Ava [Berkofsky], Kerry Washington, and me, however we additionally needed to offer Natasha [Rothwell] and Amy [Aniobi] and Mo [Marable] and Kevin [Bray] a shot. We had been glad we did, as a result of final season we had completely different administrators for nearly each episode. This yr that wasn’t as doable. However the great point is that we’ve been collectively for 5 seasons and 6 years, so everybody is aware of how we perform collectively. For that half, I’d say it was simpler than if we had been a brand new present. I feel everyone was excited to exit in an effective way and targeted on doing our greatest work. That was the simpler half.

A type of bizarre inversions the place we all know it’s going to be tougher to shoot the season however as a result of the chemistry is so good you may simply ease into it.

If it was not the final season it would’ve been more durable. However actually, I feel that as a result of it was the final season we went into it like nobody needed COVID to win.

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