‘Insecure’ Delivers the ‘90s Black Sitcom Reboot Fans Have Been Waiting For (Exclusive)

Insecure S3

Showrunner Prentice Penny breaks down season three’s “show within a show,” which pays homage to ‘Martin’ and ‘Living Single.’

Insecure is back and better than ever.

Building off the moment of season two, which earned co-creator and star Issa Rae a much-deserved Emmy nomination for Outstanding Lead Actress in a Comedy Series, the new episodes are funnier and deeper, with the storytelling pushing the HBO series beyond familiar territory.

Yes, the show is still about two friends -- Issa (Rae) and Molly (Yvonne Orji) -- navigating the ups and downs of life in Los Angeles. But with the characters now in their 30s, showrunner Prentice Penny tells ET “adulting” is the theme of the new season, with Issa forced to confront her mistakes (and hopefully learn from them), while Molly has to re-evaluate her attitude and perspective on life.

“We never wanted to people to feel like if you seen season one, then you know what to expect in season three,” Penny says about taking some unexpected risks and making some major changes to the story and characters: Episode two doesn’t include Molly; episode four draws inspiration from the Ethan Hawke and Julie Delpy romantic film Before Sunrise, with talk-heavy romantic interlude with Issa; and yes, Issa’s ex-boyfriend, Lawrence (Jay Ellis), is gone. “We really wanted to emulate real life; you don’t need to see your exes all the time,” Rae says, with Y'lan Noel’s character, Daniel, having the largest male presence in Issa’s life -- at least in the first four episodes provided to the press.

But just because Insecure is exploring new territory doesn’t mean that some of the best elements of the show are gone for good. One such example is the series’ recurring “show within a show.”

In season one, it was Conjugal Visits, a fake reality show set in a prison, while season two featured Shonda Rhimes-inspired parody Due North about a pre-Civil War South starring Regina Hall and Scott Foley. And in season three, Insecure does something Hollywood has yet to do: revive a ‘90s black sitcom.

Inspired by the real-life reboots of Full House, Roseanne and Will & Grace (and the many other series starring predominantly white casts), Penny says everyone in the writers’ room kept asking, “How come they’re not rebooting any shows with people of color?”

While TV is currently in the midst of a black renaissance thanks to Insecure and other hits series -- Atlanta, black-ish, Dear White People, Love Is__, Queen Sugar -- there have been no reboots of ‘90s black-led series put into motion, despite nostalgia for A Different World, GirlfriendsLiving Single and Moesha, among many, many others. These are the same shows that Penny says networks like the CW, Fox, UPN and WB were built on but then abandoned once they gained an audience.

The cast of 'Living Single': Queen Latifah, Kim Fields, Erika Alexander and Kim Coles. - Getty Images

“We were like, ‘Look, if no one else is going to reboot a show about us -- a black show from the ‘90s -- then we will. We’ll create our own reboot,’” Penny recalls, revealing that they came up with Kevin, an “original” series that is “very much a MartinLiving Single-type show” starring Bill Bellamy (How to Be a Player), Darryl M. Bell (A Different World) and Erika Alexander (Living Single), and then “rebooted” it for Insecure. Much like the real-life reboots, the show lives within the same concept while tackling modern social issues.

While the cast alone makes the “show within a show” even more believable, any connection between Insecure’s Molly, a black female lawyer, and Maxine, Alexander’s Living Single character who was also a black female lawyer (and very much the first of her kind on TV), is purely coincidental. “I wish I could say I tapped into that,” Penny chuckles. (Although it's worth noting that Alexander told Jezebel earlier this year she's a fan of Insecure. “I really love Issa Rae.”) 

However, the best revelation is that Kevin was directed by Alexander’s Living Single co-star Kim Fields, who played Regina Hunter. “She knows that world better than anybody,” Penny says, adding In an ideal world, “If our fake reboot could launch a real reboot, that would be the most amazing thing for sure.”

In fact, when speaking with ET in July, Kim Coles, who played Synclaire James-Jones on Living Single, suggested that a reboot might be in the works. “[Queen Latifah’s] been talking. Listen what [I'd] love to say is that I have been neither contacted nor contracted. However, something is happening next month that I cannot talk about and that’s all I’m gonna say,” she said, adding when pressed: “That’s all I can say. The six of us together; a reboot-ish. That’s all I can say.”

Until then, fans get Kevin on Insecure.

Insecure season three premieres Sunday, Aug. 12 at 10:30 p.m. ET.