The creator and star gives a behind-the-scenes glimpse at the season four premiere’s biggest reveals.
This post contains spoilers for Insecure season four, episode one.
Within the first minute of Insecure’s season four premiere, a bombshell is dropped. “Honestly,” says Issa (played by show creator Issa Rae), “I don’t fuck with Molly anymore.” The episode then jumps back in time four months, laying out how, exactly, she and her best friend got to such a broken place.
The concept was dreamt up by showrunner Prentice Penny, Rae said in a recent phone interview. For a while now, Rae had wanted to tell a nonlinear story, zigzagging between the past and present to show how things went south—“like ’90s movies used to do,” she said. Penny then pitched Rae on that surprising opening line.
“I was like, Oh, shit! Yes!” Rae said. “It aligns with a lot of what I’ve been thinking.”
This season’s plot revolves around a block party Issa is trying to throw in Inglewood. As Rae has said previously, Molly (played by Yvonne Orji) is used to being the driven, type A counterpart to Issa’s slightly more aimless slacker. But now that Issa’s got the party to organize, their relationship is getting tense. “What happens when that dynamic changes?” Rae said. “What role do you play in that friendship, and what happens when your friends look at you through old eyes?”
While Issa’s career goals are clearing up, though, her romantic life is still a question mark. In the season premiere it’s revealed she’s got a friends-with-benefits situation going on with a TSA agent played by Reggie Conquest, who happens to be plus-size. The character’s physicality was inspired by a man with whom one of the Insecure writers used be involved. “She just described what he looked like, and we were like, Oh, that’s it,” Rae said. “And thinking about it, when she mentioned that we were like, We’ve never had that representation on the show before [for Issa]. Like, duh, we should. That’s what it came down to.”
Another big reveal in this episode: this season’s parody show within the show, an Insecure tradition that has included a slave drama titled Due North and a faux ’90s sitcom titled Kev’yn. This season the parody is Looking for LaToya, a true-crime docuseries about a 26-year-old black woman who went missing in Crenshaw. The “show” is hosted by an anchor named Rose Cranberry (played by Steve Harvey Show alum Terri J. Vaughn) and includes cameos from Real Housewives of Atlanta star Porsha Williams as Tasha, LaToya’s concerned roommate, and Ray J as Rufus, LaToya’s sleazy boyfriend, who’s outraged that anyone thought they were together-together. “Boyfriend?!” he exclaims. “She said that?”
“We mock up a dream cast list and then just go out to those people and see if they’re down,” Rae said of the parody show’s casting process. Rufus in particular seemed like a perfect role for a meme-spawning Love & Hip Hop: Hollywood star.
“We just saw Rufus and were like, Oh, Ray J,” Rae said. “And he committed.”
Though the show within the show is typically a surprise, Ray J spoiled the secret last December by posting a video of himself on Instagram on the show’s set, standing alongside Williams, Vaughn,SZA, Kandi Burruss, and Carl Payne. “And the Shade Room picked it up and it was all Ray J’s fault,” Rae said, laughing.
But while past shows within the show have operated as pure parodies, fans of Insecure should note that Looking for LaToya is going to operate on a more symbolic level, Rae said.
“We always talked about the metaphor of Issa and Molly’s friendship as a murder and a whodunit, exploring the murder of this friendship and who was responsible,” Rae said. “In that way we wanted the show within a show to align with that, and it kind of does throughout the season.”
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