"Insecure" Showrunner Prentice Penny Revealed That Each Season Explores A New Theme, And I Can't Believe I Didn't Notice It Before

·4 min read

Spoiler alert: I mention the plot details of Insecure Season 5, Episode 1, so proceed at your own risk! Don't say I didn't warn you!

Now, I know ALL of you tuned into the fifth season premiere of Insecure, laughing and crying your way through its 30-minute entirety.

Still of "Insecure" featuring Yvonne Orji and Issa Rae toasting mimosas, they're both smiling

Laughing because Stanford tried to kill off Kelli (Natasha Rothwell, known for holding purses and having an awe-inspiring Stanky Legg) and crying because this is the last first episode of a season you'll get to experience.

Glen Wilson / HBO

To cope with the loss, excitement, nostalgia, and every emotion in between, BuzzFeed chatted with showrunner Prentice Penny about the series' final season.

Headshot of Prentice, he sports a mustache and wears a pinstripe shirt with a bowtie and blazer
David Livingston / Getty Images

In the interview, Prentice dished on everything from how he was brought on board by creator, star, writer, and executive producer Issa Rae to the thematic structure of each season.

Issa and Prentice at the Season 5 premiere, she wears a tan cut-out long-sleeve dress and he wears a white turtleneck with a patterned salmon suit
Jeff Kravitz / FilmMagic for HBO / Getty Images

"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," Prentice shared of the initial writing stages. "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."

According to Prentice, each season would begin with a conceptual theme that could then be explored in relation to 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,'" he explained. "Last season's theme was, 'Are the people in your life there for a reason or a season?'"

From left to right, Amanda Seales, Jay Ellis, Issa, Prentice, and Melinda Matsoukas pose for the camera

As you'll remember, last season delved into relationship conflict — particularly the one between Issa and Yvonne Orji's Molly. But Season 4 also explored discord through characters like Condola (Christina Elmore), Lawrence (Jay Ellis), Andrew (Alexander Hodge), and Nathan (Kendrick Sampson).

Charley Gallay / Getty Images

Wondering what this season's theme is? Prentice said it essentially explores the question "'Am I going to be OK if...?' So, am I going to be OK if the relationship I'm in doesn't work out? Am I going to be OK if this professional success doesn't hit the way I thought it would? Am I going to be OK if I don't find anybody? Just real questions we'd ask ourselves."

Still of "Insecure" Season 5, Episode 1, from left to right stand Natasha Rothwell, Yvonne, Issa, Amanda, and Wade Allain-Marcus, who are walking around Stanford
Raymond Liu / HBO

And you can imagine how personal the theme was to the series' cast and crew, who were bidding goodbye to a whole world six years in the making. "It was weirdly serendipitous in a way, because we were asking ourselves if we're going to be OK if we don't work together anymore."

Still of Issa from "Insecure," she looks off camera and wears a '90s-style vintage green tracksuit

I'm not crying; YOU are crying.

Glen Wilson / HBO

He continued, "Are we going to be OK 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."

Prentice poses for the camera, he wears a beige suit with blue pants, handkerchief, and tie
Barry King / Getty Images

In line with this season's theme, each episode's title ends with, "Okay?!" with the premiere called "Reunited, Okay?!" And while we're all sad to see the show go, Issa and Prentice planned for a five-season run from the very beginning.

Still from "Insecure" featuring (L - R) Yvonne, Issa, Natasha, Amanda, and Wade at a diner table

"Every show has a DNA," Prentice told Entertainment Weekly. "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."

Glen Wilson / HBO

As for the show's premier star, Issa told Variety at the fifth season screening that she's "in celebration mode." She added that "for the most part, I’m just ready to release it into the world."

Issa on the red carpet at the Emmys, she wears a see-through mesh silver gown with matching earrings
Rich Fury / Getty Images / Via youtube.com

But during a recent appearance on The Late Show With Stephen Colbert, Issa opened up about the pressure she felt to wrap the show and its characters' arcs in a neat bow, admitting that she changed the ending two weeks before filming began. She added that people even told her to not "Game of Thrones it."

Stars Yvonne and Jay also expressed the bittersweetness of the show's ending: "It is that moment where you see the chemistry and the magic, and you're like, 'Oh my gosh, this is ending. This is the last run,'" Yvonne told EW. "And I was having that moment of, we should have fun now because this is the last time we will be Issa, Molly, and Lawrence together."

Yvonne at the Season 5 premiere, she wears a metallic pink ensemble with feathered sleeves and a cut-out bustier top

Once again, YOU'RE the one crying.

Frazer Harrison / FilmMagic / Getty Images

Ultimately, Jay said he hopes people felt seen by the series: "I hope that folks feel like they got a window into a world that reflected theirs and characters that reflected them, their friendships, their romantic relationships and their work situations. Hopefully they felt seen and felt represented and got to laugh and cry along the way."

Jay at the Season 5 premiere, he wears a black fuzzy sweater and white turtleneck paired with two chain necklaces
Amy Sussman / Getty Images

You can (and better!) stream the final season of Insecure on Sundays starting at 9 p.m. ET on HBO and HBO Max.

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