The showrunner looks back on important lessons learned in season 1, the most surprising fan reactions, and his hopes for the show's legacy.
Issa Rae - Insecure

There's nothing low-key about this: Insecure, Issa Rae's hit HBO comedy, returns for its fifth and final season with one question on its mind.

"'Am I going to be okay?' is a huge theme for really all of the characters this year," showrunner Prentice Penny tells EW.

When we last left off with the series, Issa (Rae) and Molly (Yvonne Orji) took the first step toward mending their broken friendship. Meanwhile, Issa was trying to decide whether she wanted to dive back into a relationship with Lawrence (Jay Ellis), who not only got a job in San Francisco but also found out his ex-girlfriend Condola was pregnant. The status of these pivotal relationships in Issa's life remain up in the air as we head into the farewell season.

Ahead of the premiere (Sunday night on HBO), EW spoke to Penny about the show's remarkable run, surprising fan reactions, and more. (Note: Some of these quotes also appeared in EW's recent Insecure digital cover story.)

Insecure, Prentice Penny
Issa Rae and Yvonne on 'Insecure' (inset: Prentice Penny)
| Credit: Raymond Liu/HBO; Kevin Winter/Getty Images

ENTERTAINMENT WEEKLY: What are you most proud of when you look back at Insecure's journey? 

PRENTICE PENNY: All of season 1 holds a special place in my heart because it was like the show didn't exist yet in the world we live in. It felt like something special that [star and co-creator Issa Rae], [executive producer Melina Matsoukas], me, and all the writers were doing over in the corner — like when you're a kid and you're drawing a little picture at school and you're like, "Nobody's judged it yet." You're being the most creative you can be because there's nothing stopping you from that. Outside of the show, I'm the most proud of breaking new writers and breaking new directors and new Black talent when I have had the chance. [I wanted to] leave the Black writer, director, and actor pool better than when I found it. That is something I'm super, super proud of in the legacy of the show.

In those early days, what were the most crucial decisions you all made that contributed to the show's success?

A lot of the things that we had in the back half of season 1 ended up moving to the front half. The end of the first season, when we initially broke it, was Issa sleeping with Daniel [Y'lan Noel]. [HBO] was like, "No, no, no, make that happen in the middle." We were like, "But what do we have for the end?" "You'll figure it out." They were right. That was the most interesting stuff, and we were kind of stalling the story. It was just a good thing to know — "No, no, no, just keep pinning yourself into a corner and figuring out how to get out of there." The other lesson we learned early on was anything that got a strong debate in the writers' room, that's going in the show.

What sparked the most debate in the room?

I remember one specific thing at the end of episode 7 in season 1: In the fundraiser scene where Issa and Molly are having an argument because Molly helped Issa not get busted by Lawrence and Daniel. I think I typed Issa saying to Molly, "Are you just jealous because I can keep a n‑‑‑‑?" One of our EPs, Amy Aniobi, was like, "Oh, hell no. She can't say that to her. If she said that, I would tell my friend, 'F‑‑‑ you, you're not my friend.'" Amy and I started debating it, and then the room started debating it, and that's when it was like, "If we're arguing it, then the audience will also have the same visceral reaction."

It was around episode 6 and 7 when we were having these arguments. It was around the same time that Molly was dating Langston Kerman, who played Jared, and it was like, "How come women can have gay experiences and not be gay, but men can't?" We were also having that same argument in the room, and the girls actually had that argument on the show. So it was around the same time we were doing both of those episodes, and that just became our thing: If we're arguing about it, it's going in the show.

Natasha Rothwell, Yvonne Orji, Issa Rae, Amanda Seales, and Wade Allain-Marcus on 'Insecure'
| Credit: Raymond Liu/HBO

Was there ever something you discovered organically that changed the course of the series?

One of the things we learned early, even in the pilot, was just how great of an improv [duo] Issa and Yvonne would be together. It was the same with Maya Erksine, who obviously is amazing on PEN15, but when she was playing Molly's friend at work Diane, it's like you [could] just give her anything and be like, "Oh, she's going to make it better." Same with us casting [consulting producer Natasha Rothwell]. She was never intended to be Kelli; she was there to write. But when she would read Kelli at our table reads, we were always laughing. We just gave her the part. We never brought anybody else in.

Insecure has a very vocal fan base. What has been the most surprising fan reaction?

I was surprised that people had a lot of Molly hate in season 4. We thought the Issa-Molly thing might be a little bit more split down the middle, who was mad at who. But it was definitely more 70/30, people mad at Molly than Issa. What I surmised from it was, Issa is our main character no matter what — and if people have to choose, they're going to choose the character we've been following emotionally for so long.

The other thing I'm always surprised by is the small things that people get caught up in, which is the little things we write as jokes that people start QAnon-ing about. We had one joke when Tiffany [Amanda Seales] is like, "Derek lived in a hotel one year." [Fans were] like, "Oh my God, that's not Derek's baby! Simone is not Derek's baby." It's just like, "No, that's his baby. We've done nothing."

When the final season was announced, both you and Issa said you've always thought of this as being a five-season show. How did you settle on five being it?

I think we both said it at the same time. We were like, "How long do you want to do the show for? Look, we'll say our answer on the count of three," and we both said five. It felt like the right amount of time to do a show. We could have been way off, who knows? But I think at the same time it felt like, knowing how long it takes us to make this show, that it would be five years of our life and that's a good amount of time to not overstay your welcome. I'm still leaving when people still want us around.

I think one of the things I learned too from [my work on other] shows is that every show has a DNA. Some shows are only supposed to be 10 episodes a season and sometimes they'll be like, "Oh, the show's a hit. Let's do 20 of them," and you go, "Oh, the show's not that good anymore." It's like, well the show's not good anymore because the show's DNA is not supposed to withhold that many episodes. We always looked at our show as, "It isn't meant to be 90 episodes." We never wavered. I think we just felt that's the right amount of time to tell these characters' stories.

Insecure ep 8 “Lowkey Happy” Jay Ellis, Issa Rae
Issa Rae and Jay Ellis on 'Insecure'
| Credit: Merie W. Wallace/HBO

Coming into season 5, did you look to past shows for the dos and don'ts of final seasons?

A show that we looked towards was Six Feet Under. We thought that their finale was really strong. That was the barometer we used, because initially we put a lot of pressure on ourselves. We kept trying to end their stories and [using] the analogy, "We have to land the plane for all these characters." One day Amy said, "We got to stop thinking about it like [that]." We had to think of these characters' lives will continue. It's just the writers are jumping out of the plane. [We started thinking] if we were going to do a season 6, what would be an interesting starting point for the characters? Then let's end season 5 that way.

How would you tease what to expect from the final season?

I think Issa and I always said the last season [would be about], "Am I going to be okay?" Which is what we all want to know. The show is called Insecure, and when you have insecurities, what you're really saying is, "I'm not okay in these areas of my life." What we wanted to answer in the last season was, "Am I going to be okay if this relationship doesn't work out? Am I going to be okay if this friendship goes away?" Sometimes you aren't dealt the cards you wanted, and then [the question becomes] how do you respond? Can you find a way to be happy? Can you find a way to still thrive?

What do you hope the legacy of the show is?

I guess I hope the legacy of this show… I don't know. I feel like legacy is always for other people to figure out. When you're in it, you're not trying to think about legacy. I can say what a legacy thing means to me, and this is what I would want for the show. So growing up, I was a huge fan of The Cosby Show. Why I was a huge fan of The Cosby Show was [because] I was seeing Black characters that were like my mom and my dad and my friends. My mom was a lawyer, my mom was an AKA like Clair Huxtable was. My best friend's dad was a doctor. My dad did real estate and had his own business. So I was watching families figure it out and it wasn't about the struggle or about, "We're poor. We don't have nothing," typically the way that a lot of Black shows in the '70s are, like Good Times and Diff'rent Strokes. What [The Cosby Show] meant to me was it inspired me to believe that I could write and I could tell my story.

So what I would hope for the legacy of our show is that it inspires the next generations of writers to want to continue to see themselves on screen — Black writers and writers of color to want to continue to say, "Hey, I see myself on screen. That is possible, so let me do it for my show." So that's what I would the legacy is: It would inspire the next generation of Black and people of color writers to want to seem themselves and tell their stories on screen and to know they're as valid as anybody else.

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