SPOILER ALERT: Do not read if you have not watched the first three episodes of season 5 of “Insecure:” “Reunited, Okay?!,” “Growth, Okay?!” and “Pressure, Okay?”
For the last few weeks, “Insecure” star and co-creator Issa Rae has been focused on toasting the end of the show, basking in the last few moments when the final season is known only to her and the cast and crew behind the show.
“That’s why I’m so bent on celebrating. I’m like let’s celebrate when y’all like it right now. Let’s celebrate the nostalgia before all hell breaks loose,” Rae tells Variety with a laugh.
“People are gonna have many opinions about the second half of the season, I just know they are,” she continues. “And I can’t please everyone, so I just want to live in the positivity as long as I can.”
But on Sunday night, it was time to finally hand the show back to the fans with the kickoff episode of Season 5, titled “Reunited, Okay?!” Rae explained that this season’s titles will all have that exclamation incorporated, a reference to an exclamation she regularly uses in her own speech and a nod to the larger questions the episodes are exploring.
“We applied that to every character because that’s something you wonder when you’re going into this stage of your life, you’re just like, ‘Am I gonna be OK?’” Rae explains.
The 30-minute episode (yes, the show is still only a half-hour long) followed Issa Dee (Rae), Molly (Yvonne Orji), Kelli (Natasha Rothwell), Tiffany (Amanda Seales) and Derek (Wade Allain-Marcus) back to their alma mater Stanford University for their 10-year reunion.
The trip back to their old stomping grounds was full of emotional highs and lows for the characters as they grappled with who they thought they’d become back then versus who they are now. Looming over the trip were a few major questions, while Molly, now single after her breakup with Andrew (Alexander Hodge), was focused on bettering herself and repairing her friendship with Issa, whose own relationship drama was the elephant in the room.
At the end of Season 4, fans were left shell-shocked when Issa and Lawrence’s newly rekindled relationship was rocked by the news that his ex-girlfriend Condola (Christina Elmore) was expecting their baby. So what’s their status now?
The Season 5 premiere answered that question and more, and here Rae shares some insight into the creative process that went into developing the episode.
Issa and Lawrence’s Breakup
In the final moments of the episode, Issa and Lawrence finally said (or rather didn’t say) what was left unspoken between them in the Season 4 finale.
At first it seemed like all was well for the couple, with Lawrence picking Issa up from the airport and greeting her with a kiss. But on the car ride home, their conversation quickly grew stale, with the couple talking about the brightness of the moon and their plans for takeout instead of the existential experience Issa just went through during her trip back to her alma mater.
Something changed and Lawrence could tell.
When they parked outside Issa’s apartment complex, he grabbed her bag from the trunk and began to walk toward the door, asking “Should we?”
“Um, Lawrence I had a chance to think, and…” Issa began, choking up and unable to say more.
“Yeah. Yeah, I know,” he replied.
There was no big blow up or a “this isn’t going to work” admission, just silence — and mutual understanding — lingered between them as Issa took her bag and walked inside, leaving Lawrence standing alone as the episode cut to black.
“In crafting the first episode we wanted to remind people about what the most important relationship in the show is — and that was like getting back to Issa and Molly’s relationship,” Rae says. “It was important to me that that be addressed first and that we focus on that relationship story-wise and use that as a way to also inform where Issa’s headspace was as it relates to this situation that happened with Lawrence.”
Ultimately, Rae adds, the trip “really just helped [Issa] to make the decision that is best for her. And so we hope that viewers will see that as well.”
Teasing Issa Dee’s evolution this season, Rae says that the show will focus on those larger themes of Issa trying to figure out who she is and where’s she’s going.
“It’s always been my goal to answer that by the end of this series,” Rae explains. “So, that’s the journey that we’re watching Issa go on or that’s, I guess, the beginning of the end. But the idea of her finally being confident in that bit of who she is and her path just makes me so happy and satisfies me as a viewer.”
So, are Issa and Molly “Back Back”?
That remans to be determined, but after being set up to be robbed by their old college frenemy, it certainly seemed like Issa and Molly were on their way to getting their friendship on track.
While to some extent, Rae has known how she wants to wrap up “Insecure” for some time (despite re-writing the finale episode two weeks before filming started), finding the right way to pilot these characters toward the show’s end required “lots of discussion and self-reflection.”
“I asked myself just as a viewer what I wanted to see for this character — and then also as a person who influenced the character heavily, what I wanted to see for myself and this character, what I wanted her journey to be,” Rae says.
As far as that relationship with Molly goes, Rae wants to show how good they are for each other, especially after they “blew so much of it up” last season.
Orji is especially ready for some redemption, after fans railed on Molly (and Orji) on social media for much of the year. Sure, the work resulted in Orji’s first Emmy nomination (for supporting comedy actress, while Rae was nominated in the lead category once again), but the experience certainly wasn’t fun.
“Molly should have never actually been crucified on anybody’s cross, because she’s been a good friend. She’s been a darn good friend actually,” Orji argued at the show’s red carpet premiere. “But you know what, she did have some missteps.”
Last week, Rae and Orji watched all of season four together during the fan watch-along screening and the experience was somewhat illuminating for Orji, who admits that “Molly didn’t have her best moments all theme. But sometimes, out of the ashes, we rise.”
Who Came Up with “Prenny’s Preguntas”?
In the lead-up to the big breakup, Kelli sat before a microphone, recording a message for her listeners (who she calls the Kelli Klan), saying, “I know it’s been a minute but I’m back with a question for y’all — if you knew the end was coming, how would you make the most of your time left? What legacy would you want to leave behind? How would you want to be remembered?”
With Ego Ella May’s “Give a Little” playing in the background and a montage of the core four characters as they seemed to ponder where they were at in life and wonder where they were going, the dialogue took on a meta meaning. But, in typical Kelli fashion, things weren’t super serious for long — with the punchline coming in when she revealed the podcast is called “Prenny’s Preguntas.”
Some fans may already know that the character’s last name (Prenny) comes from showrunner Prentice Penny’s childhood nickname.
“But the preguntas came from Season 1 when they’re in Malibu and Issa makes an offhanded joke [to Kelli], ‘Do you ever hear yourself?’ And she’s like, ‘Of course, I do, I have a podcast,’” Penny explains. “And we were like, ‘Oh, we should see this podcast finally.'”
“Insecure” is known for creating shows within the show, including Season 2’s ‘Due North,” the play on “Underground” and “Scandal” that starred Regina Hall and Scott Foley, Season 3’s “Kev’yn,” a fictional ’90s sitcom reboot and Season 4’s true crime tale “Looking for LaToya.”
Beyond feeling like it was the right time to make the callback, Penny explained that the questions Kelli asked align with the larger thematic goals for this season.
“The preguntas — asking questions — rears its head a lot this season in just having the characters go back to square one,” he said. “Going back to Stanford in the premiere and kind of going back home — sometimes you’ve got to go there to figure out, “Who am I? Who do I want to be? What did I say I want it to be?” so it just felt like a natural way to have it.”
Stanford alumni return to campus on screen and in real life this weekend, all for Reunion Homecoming. Catch the Season 5 premiere of @insecurehbo on Sunday at 10/9c, starring @IssaRae, '07, and written by @amyaniobi, '06.
— Stanford University (@Stanford) October 22, 2021
Rae’s Real-Life Homecoming
The premiere episode, directed by Melina Matsoukas, primarily took place on the Stanford University campus in Northern California, marking a major return for Rae (class of 2007) and executive producer Amy Aniobi (’06), who wrote the episode. The duo met while in college, first collaborating on Rae’s web series “The Misadventures of Awkward Black Girl.”
Recounting the experience, Rae marvels at how supportive the Stanford team was: “They’ve never let anybody film on campus before, so that was such an honor and a privilege to just revisit campus in that way.”
While Issa Dee’s experience returning to her Alma mater (and speaking on that “finding your path” alumni panel) might have been a little awkward, things were much more stellar for Rae. “It felt like some boss shit to be like, ‘Here’s my camera crew. Now I’m paying y’all in a different way,” she says.
Rae has been contemplating the legacy of “Insecure” as the show comes to a close, and she says now, “Most of me is ready to move on; I already have moved on. But these last couple of weeks have allowed me to live in the show, and what it is, and what it represents.”
“Now my eye is just toward how it will be received over time. I think the immediate is less important to me, but like the series as a whole: Will it stay in people’s hearts?” she continues.
When it comes to her own personal journey, Rae admits that moving past “Insecure” and into the unknown is “the scary part of it.” But she remains committed to “making shit that I want to see.”
“Whether or not people fuck with it, or buy it, or whatever it is, that’s just my No. 1 goal is to continue to create and collaborate with the creators and the content that I want to see,” she says.
As far as “Insecure” goes, Rae has found it incredible to see the impact of the show on the television landscape.
“I see it even in stuff that I’m pitched, which is incredible. Where people are like, ‘It’s kind of like ‘Insecure’ meets this and it’s just like, we used to use other shows [as examples] and now we are that,” she says.
Rae notes that she’s particularly proud to see the show’s model in the mandates that people issue for their own crews and their own representation, while she’s a little less thrilled to see the white shows use “Insecure” as their template without credit.
“But I think that currently we’re embedded in the culture in a way that I’m so grateful for, and I hope it remains that way,” she says.
Molly’s New Look
Following a time jump to one year after the season premiere episode, Issa and Molly have found themselves rebuilding their friendship — meeting up for pasta and wine after work and celebrating “Freaky Friday” (by watching “Any Given Sunday”), plus Issa bought Molly her own pillow for nights when she sleeps over. (“Your head kept deflating mine,” Issa teased.) But most importantly, the pillow (and a paisley headscarf) were tasked with keeping Molly’s new fade fresh. Yes, attorney Molly Carter is now rocking a cropped coif in the boardroom and (Issa’s) bedroom.
Orji opened up about Molly’s hair journey in season five, describing the new ‘do as “very freeing.”
“When Issa and Melina said, ‘Molly should have her hair short..’ I said, ‘Oh, you all made my life easy,’ cuz, you know, just dealing with the pull and the tugging of wigs [sighs], it was a lot,” Orji explains.
Plus, Orji notes, she’d gone natural at the beginning of quarantine, so it was a relief that the creative team agreed that her chop fit with the character. “I love that they put that in.”
Penny added his two cents while tweeting along with fans during Sunday night’s episode: “We wanted to embrace Molly doing the chop with her hair. She has some cleansing to do.”
Nice to Meet You Crenshawn
Episode two also introduced Kofi Siriboe, whose appearance in the Season 5 trailer sent tongues wagging — though the nature of his guest starring role was unknown. Siriboe ultimately played an fashion designer named Crenshawn, whose designs comment on the prison system and who employs other formerly incarcerated artists to help craft them.
The episode’s plot revolves around Issa and The Blocc working to produce Crenshawn’s community fashion show, with Issa (assisted by Courtney Taylor’s hilarious Quoia) trying to figure out how to navigate the demands from the water brand she’s nabbed to sponsor the event, while maintaining the artist’s vision.
Rae shares that Siriboe ended up winning the role for a few reasons — first being that they’re really good friends.
“With the Crenshawn character, we had like a Nipsey [Hussle] in mind, another artist prototype that matched the love of LA that Issa has,” she explains. “So, in thinking about that character and what he looked like, Kofi was one of the biggest Nipsey fans, and just being from LA, I was just like, “Oh, it’s so cool to have him in this world,” especially just as a passionate person I know him to be too.”
And after starring on “Queen Sugar,” “Girls Trip” and the romantic drama “Really Love,” it’s obvious Siriboe has the range, with Rae confirming that the actor really embodied what the “Insecure” team was aiming for.
Episode 3 introduced Lela Rochon as Condola’s mother Jackie and Keke Palmer as her sister Kira. Rae explained that the casting for Palmer (who’s been a longtime and very vocal supporter of the show) was its own inside joke, coming after the star tweeted that she wanted to beat Condola down for getting in between Issa and Lawrence.
“I saw that tweet from Keke and it cracked me up. And then I was like ‘Okay, say less.’ And then as we were crafting the story, we came up with this idea for Condola’s sister,” Rae said. “And given the context of Keke’s original tweet about beating Condola’s ass, I thought it’d be funny to have her be Condola’s ally instead. So she came on set like, ‘Okay, I see what you did there.’”
“Insecure” airs Sundays at 10 p.m. on HBO.