It still hasn't completely set in that Insecure is coming to an end. For the past five years, Insecure delivered an authentic and unapologetic depiction of Black people that made me feel like I was watching my friends and family on screen. From the hilarious situations that would happen within their deep-rooted friendships to the genuine discourse that would take place on Twitter during each episode, the series felt like home for a lot of us.
In an attempt to block the tears and celebrate five glorious seasons, I sat down with Insecure's showrunner and executive producer Prentice Penny — who's also written and directed episodes for the series — to learn what it was like being a part of such a groundbreaking show from beginning to end.
1. Prentice Penny wrote a letter to Issa Rae, telling her why he'd make an excellent showrunner for her show.
"In the letter, I was basically telling her why I thought I would be a good showrunner to partner with. I talked about what I connected to in the script; I talked about currently being the only Black writer on white shelves for like the last seven years at that time; I talked about us both being from View Park/Leimert Park/Crenshaw area and how I wanted to make those areas feel dope; I talked about working at a nonprofit before I was a writer, so I understood that specific world. And then, of course, I talked about why I thought she was dope and how what she was doing was so interesting. I just wanted to be a part of it. And if she didn't go with me, I let her know I'd still be a resource for her — and I meant it."
2. The whereabouts of the letter are still unknown.
"I'm sure I have it as a file on a different computer. Now I'm curious if I have the letter, that's actually funny. I'm gonna look! Issa might have it."
3. Neither Prentice nor Issa were familiar with the other's work before joining forces together on Insecure.
"I'd never seen [Awkward Black Girl]. She didn't ask me, and if she did, I'm sure I would've lied [laughs]. Before I met with her, I think I saw like one episode, and it was so different than the Insecure script. That's what was so interesting, because she had never read anything I wrote either, and I never asked her. We were basically just like, 'Look, if you're playing at this level, you obviously have talent.' Issa knew I'd been working for like 11 years in the business, and she got a show on HBO, so we're obviously somewhat talented."
4. Their initial meeting only lasted about 15 minutes.
"We just talked for like 15 minutes. It was really a vibe meeting. We definitely did not overthink this scenario at all. It was just a feel. I'm just thankful. I'm blessed that it worked out — not even the show's success, because you can't predict it — it was more about us having a great working relationship. We just loved working together, because we worked together so well."
5. Prentice and Issa have a brother/sister relationship.
"We're like brother and sister. Weirdly, I don't think we've ever had real disagreements. I mean, we've disagreed on things — we can disagree all day, but she'll always be the deciding vote; it's her show. You know, we can disagree all day. Issa birthed this baby and I say that me coming on the show is like the best stepfather that the show could ever have."
6. Preparing concepts for episodes stemmed from their personal lives.
"Before we meet with the writers, a lot of times Issa and I just drink a lot of champagne and talk about what our friends have been going through and what we've been going through. Then we will take those ideas and try to find the theme of a season — sometimes it comes early, sometimes it comes while we're talking with the other writers, and then we sort of share those ideas with the other writers. After, we go on a retreat, which is like three days, and we kind of just take those ideas and they share their own stories (i.e. what they're going through, their dating life, family, careers, etc.), and that's how we start to form our episodes. It's almost like taking a lump of clay and then you continue to mold it into something.
It's kind of like solving a puzzle; you do the borders first, because that's the easiest part, right? Then you have to think about the big ticket things you want to say, like where do we want to end the trajectory of a character or situation wise, and then you start filling in the smaller details of the story."
7. Halfway through each season, an event happens that shakes things up and propels the audience to what the focus of the second half of the season will be.
"We always know halfway through that there will be some sort of thrust to the second half of the season. In Season 1, Issa sleeps with Daniel — that made audiences say, 'Oh snap, now the game is different.' In Season 3, Issa meets Nathan and Lawrence returns. And last year in Season 4, Molly and Issa fight at the block party. There's a midway push to the second half of the season — it's almost like we're building two arcs for our show."
8. The infamous Coachella episode was inspired by a crew member attending the festival.
"The Coachella episode was actually inspired by one of our writers who was going to Coachella. We were like, 'Oh, that's interesting! Is there an episode there, where we could have them travel?' It was Beyoncé — Beychella — so it was a major pop culture moment in real life too, so that was big for us."
8. Lawrence's wild threesome really happened to Prentice's friend.
"In Season 2's 'Hella LA,' when Lawrence has a threesome, that happened to a friend of mine when he was divorced. He literally walked into a store and it just happened. They went back to the house and these white women sort of fetishized him as a Black man. He was newly divorced, so he was like, 'Oh, these are the streets now?! I'm not built for this!' So, episode ideas can start from a very compact conceptual thing or a small personal story, and then we try to tailor these ideas for our audience."
9. Prentice used his traffic stop run-in with police as a reference for Lawrence in Season 2, Episode 4.
"This police officer pulled me over and I was like, 'Oh my God.' It got very tense because soon there were like four cops there, just for a traffic stop. I went to USC, so I have a USC license plate holder around my actual license plate, and one of the cops noticed it. Next thing you know, he just starts cracking jokes with me because he was a UCLA fan. I was just so shook at that point about where that situation could have gone, that I had to now entertain this white cop's jokes."
10. Wendy Raquel Robinson's tearful scene with Issa mirrored a writer's experience with her mom.
"Last year, we had the amazing Wendy Raquel Robinson play Issa's mom. There's a scene where she sees Issa and is just like, 'Come here,' and Issa looks at her confused. Wendy's character can tell something's wrong with her daughter, so again she tells Issa, 'Come here.' Finally, Issa breaks down in tears and goes to embrace her mom in a hug. That actually happened to one of our writers. One of our writers was in New York trying to hustle and when she went back home, her mom just looked at her, and was like, 'Come here.' It played out the same way it did between Issa and Wendy Raquel. We just thought that was so beautiful and we knew we had to add it to the show."
11. The decision to have Issa ignore Molly when she sees her eating at their favorite restaurant was inspired by an event that happened to one of the show's writers.
"When Issa and Molly are arguing and Issa sees Molly in the restaurant but doesn't go in to speak to her, that happened to a writer of ours. She saw her friend in the restaurant they used to go to together all the time, but didn't speak to her because she wasn't ready to have that conversation with them yet. Her friend even saw her and made eye contact, so this was a real thing. The last five years and seasons have all been inspired by people's real stories on that screen."
12. Each season has a theme.
"The themes were always things that we would conceptualize and we would build it off of the previous season. With Season 1, we see the characters making a lot of mistakes, so the theme for Season 2 was, 'I know better, so I have to do better.' Last season's theme was, 'Are the people in your life there for a reason or a season?' We wanted to explore that with Molly and Issa's friendship, as well as relationships with people like Condola, Lawrence, Andrew, and Nathan — are they here for a good time or a long time? This season's theme is, 'Am I going to be okay if...?' So, am I going to be okay if the relationship I'm in doesn't work out? Am I going to be okay if this professional success doesn't hit the way I thought it would? Am I going to be okay if I don't find anybody? Just real questions we'd ask ourselves."
13. Season 5's theme hit home for the cast and crew.
"It was weirdly serendipitous in a way, because we were asking ourselves if we're going to be okay if we don't work together anymore. Are we going to be okay once this show's off the air? It was hard for us to answer these questions, because we've been in our own close bubble for six years. This show has affected all of our lives in a very intense way."
14. Prentice's favorite behind-the-scenes memory with the cast involves Essence Fest.
"One of my favorite moments — there's two — was the first two years that we were at Essence Fest in New Orleans, because the first year we were there we premiered the series. Nobody knew who we were, so we were walking through the French Quarter just happy to be there and excited because we were two months away from the show officially coming out. We had just finished the season, so being in New Orleans gave us the chance to really hang out and let loose. It was so much fun!
When we came back within a calendar year, we had to get escorted to the hotel and all we could hear was people screaming, 'Issa, Lawrence, Molly!' Then when we got to the area where they were showing the episode, we had to be escorted through the back way and underground tunnel. It was crazy how much things changed in a year. We got to witness both sides of fame and that was just a fun thing that we got to do."
15. Champagne is the catalyst for a great episode!
"When it comes to series rituals, the crew retreat is probably the most consistent thing we do. For Issa and I, we'd always sit around the pool, drinking champagne. That's probably the ritual I'll miss the most, because we'd just talk for like eight hours and it was great."
16. Prentice and Issa didn't realize they'd use Wade Allain-Marcus's character as much as they did.
"Sometimes you don't really know until you see it on the screen. Issa and I didn't really realize how much we would use Derek DuBois (Wade Allain-Marcus). He's truly great. One of the most important things we have to consider is how that character impacts the other characters. They have to impact them in a real way, and we saw that with Derek and Lawrence. Derek was the friend who would ground Lawrence, while Chad (Neil Brown Jr.) provided the comedic relief. Chad is so bold that we had to give him a weakness and that weakness was his need to always try to impress Derek. It's a fun dynamic. Lawrence, Derek, and Chad were just so great together."
17. Three actors who auditioned to play Lawrence scored other roles in the show.
"The two parts that we had to test early for the pilot were Lawrence and Molly. For Lawrence, we tested Jay Ellis, who obviously ended up being Lawrence. We also tested Y'lan Noel (Daniel), Neil Brown Jr. (Chad), and Leonard Robinson (Taurean) for Lawrence. Okay, all those four, all the way up for Lawrence. We knew immediately that they were our top four, because they all brought something different. So then we did a chemistry read with Issa in front of HBO and it was clear Jay was our Lawrence. But the chemistry read was also where we quickly realized that Y'lan would be our Daniel, because he had this swaggy energy. He was the guy you want to sleep with."
18. Neil nailed his following audition on the first try.
"When we had the role of Chad come up, Neil was the first one to come in for that, and he crushed it! Wade came in behind him and he was good, but he wasn't Neil. We also brought Leonard in for Chad and he was great too.
All the people you see on Insecure either went up for the role they're in now or others, like the next tier role, and got it. That's really how it happened, especially for the guys. We were just blessed with very talented people."
19. Conjugal Visits, one of Insecure's many "shows within a show" was inspired by Locked Up Abroad.
"All of the shows happened very organically. I forget how Conjugal Visits got started. I think a lot of us were watching Locked Up Abroad and other shows like that. And as we were watching, we thought about how they rarely focus on women in these shows. Now, I think Netflix has a show called Jailbirds, which is about female prisons."
20. The concept for Due North grew from an inside joke about two writers on the show.
"Due North happened because two writers, a Black writer and a white writer, were having lunch. He was married and she's single. There was literally nothing between them, but we just started making up this thing that they had snuck off together. It was just a bit that snowballed. His last name is Dougan and her last name is North, so when we added the slave narrative, we knew we had to call it Due North. Empire and Scandal were poppin' at the time, and Underground was on, so we were like, 'What if we made this like Underground meets Scandal?'"
21. Due North stars Scott Foley and Regina Hall were on the writers' casting wish list.
"Ben Cory Jones and Natasha Rothwell, who wrote Due North, put together a wish list, and Scott Foley and Regina Hall were on there. They both happened to be fans of the show, so they immediately said, 'Yes!' Once that happened, we were able to get Michael Jai White. It became a real show."
22. The resurgence of reboots gave them the idea to create Kev'yn.
"Everybody has been doing reboots of sitcoms, and we were like, 'Why aren't they rebooting Black sitcoms?' So we decided to reboot our own sitcom. We did our version of a Martin-style show with Kev'yn, starring Bill Bellamy, Erika Alexander, and Darryl M. Bell. Then, of course, we had the lovely Kim Fields direct it."
23. Looking for LaToya explored the reality of missing Black girls and women in the US.
"Looking for LaToya was inspired by all the crime podcasts that've been happening, like Serial. We wanted to do one asking why nobody's looking for Black women."
24. There was one show idea that just didn't make its way off the ground.
"I think we were forcing it. It was called Back to Africa — it was a genealogy show, but nobody was really that excited about it. That taught us that we can't just come up with a 'show within a show.' It has to happen organically, usually because somebody does something and it'll snowball from there. I think this was around Season 3 and nobody really got on board. It really wasn't until the reboot stuff (Kev'yn) that we all got excited about rebooting a multi-cam because it was so different for our show to use them."
25. Part of the reason why the show made Molly and Issa fall out is because they were so close.
"It felt like the right time to do it, because they know all the dirt about each other. The good side of being so tight with someone is that you know all this stuff about them, but knowing all that information can also work against the friendship. It can be hard to let somebody grow when you know all the dirt about them, because you can you use it to weaponize. We felt like it was an interesting time to explore that because we never wanted them to be frenemies. They're real friends, but even friendships can be challenging. So we wanted to really explore that relationship and the backbone of that."
26. Prentice refuses to choose between Molly and Issa. Instead, he's focused on how they'll rebuild their relationship.
"I'm not 'team' anybody. I'm #TeamRelationship for them. We were all really surprised by the Molly backlash, because in reality, Issa stays tricking Molly into getting into stuff, Issa's always lying to her...Issa's a user, and she does it a lot! Obviously, Molly's done things too, but like at the fundraiser, Molly literally had Issa's back when she helped hide the cheating mess with Lawrence and Daniel, and then Issa turns around and says, 'You're jealous because I can keep a dude.' It sucks! She just helped you do this cheating thing and then you go sideways on her?"
27. Prentice has an idea about why people side with Issa more than they do Molly.
"But what we probably did anticipate was that if there was a split between the two of them, the audience would probably naturally side with the person whose show it is (i.e. Issa). We probably should have made more of the fights be Issa's fault and skewed it so that instead of it being 50/50, we could make it more 60/40 or 70/30. I also think Molly gets a little bit more backlash just because the character can be a little bit more guarded about her flaws, whereas Issa kind of wears her flaws on the surface.
I also feel like Molly's like most people, but I think most people don't like seeing themselves. I know a lot of Mollys and I know a lot of Mollys who did not like Molly. People throw a lot of shade at Molly, but there are a lot of people like Molly."
28. "Fans can expect unapologetic honesty from these characters in Season 5."
"Nobody's holding back anything, so let's see where that gets them. We always viewed this season as the characters' lives are not ending, it's just that the writers and the audience won't be watching them anymore. We never wanted to write an ending. We always wanted to write it like this is the next phase of their lives, and if you were to watch Season 6, these are the stories we would be telling in this world."
Be sure to catch the fifth and final season of Insecure on Sundays at 10 p.m. EST on HBO, or you can stream it every Sunday, at the same time, on HBO Max.