Prentice Penny is the showrunner for HBO’s Insecure.
PHOTOS – Jeff Kravitz/FilmMagic For HBO; Getty Images ILLUSTRATION: Isabella Carapella/HuffPost

As any “Insecure” superfan could attest, the road to success for heroine Issa Dee (series creator Issa Rae) has been long and riddled with disappointment, full of cases where she got overlooked in favor of a white face. Issa now reaps the rewards of her years as an entrepreneur and successful entrepreneur in the fifth season. Even more importantly, she’s bringing other Black folks with her.

It’s a journey showrunner Prentice Penny recognizes intimately. Though he cut his teeth as a writer on the show “Girlfriends” in the early aughts, he later had to navigate myriad predominantly white writers’ rooms. But since the massive success of “Insecure,” he’s become a vocal advocate for other Black talent, even serving as a producer on the HBO variety series “Pause with Sam Jay” and launching a comic book companyFostering marginalized voices

Still, like Rae’s character in the Season Five premiere, Penny sometimes catches himself second-guessing whether he’s worth his salt. “I’m probably still working on if I’m any good,” he admits on a recent call from his native Los Angeles. He thinks about that some more, then explains: It’s not so much that he’s questioned his talent, but rather his confidence in it.

“I would say maybe less good ― I’ve had markers where I felt more comfortable,” he says. “When [creator] Mara [Brock Akil] officially hired me as a writer on ‘Girlfriends,’ [that]It was definitely a landmark thing. Like, ’Wow! Someone I admire so much actually believes that I’m talented.′

That feeling was further validated when “Insecure” premiered in 2016 and instantly clinched the support of Black Twitter. “‘Insecure’ coming out the first season and people responding to it — I think it was a big sigh of relief that Issa and [my] debt on each other was paying off.”

Penny often thinks about the indicators that helped him remember he was on track when he considered this question of success. “I got to deliver a show, from hiring writers and directors and running a writers’ room. Until you hike the mountain, you don’t really know if you can get over it.”

But it shouldn’t come as a surprise, least of all to him, that he’s made it this far. After all, he’s been preparing for this moment since long before “Girlfriends” came calling, when he was growing up just eight miles away from Hollywood. His mother even told him about Los Angeles County Superior Court. Judge Brenda PennyThat he knew he was a storyteller and that Spike Lee was his only source of inspiration in Hollywood.

“From the moment I said I wanted to do that, my mom could not have been more supportive,” Penny says. “Especially at a time when a lot of parents wanted her to encourage me to go into things that were more stable — like doctor, lawyer, engineer.” He understands the reluctance, though. “I don’t really fault that. It was almost like, ′He should be a magician.’”

Penny attributes a lot of his ability to carve his own path in Hollywood to his family ― “on my father’s side particularly,” he says, “as they were sort of less college-educated and more self-motivated entrepreneurs.”

He recalls their words of advice: “′You can get it if you really want it. It’s possible. Do what you got to do to make it happen.′ Unapologetically speaking up for yourself, and advocating for yourself, was a big thing on that side of the family.”

Penny is still amazed at his success as a man, even today. “[He] ran away from Kansas City when he was 14 and was a hobo,” he says. “Then [he]He became a successful businessman, and was among the first Black families in Baldwin Hills. I can’t tell that guy, ‘I can’t make it happen.’ He was like, ‘I was a hobo.’”

Penny puts that same energy into his work as a writer. He says it is like being an entrepreneur, just like his father. “Everything you kill, you earn,” he says. “It’s not like you’re in a company. It’s just you. You might work on a show, but after you leave that show, you’re just you again.”

Coincidentally, this is where the writer-producer-showrunner is today — reveling in the triumph of “Insecure” as it bows out while considering what he wants to do with his success. This is similar to Rae’s name-character on the show. It means helping others.

Writer/producer Prentice Penny and actor/producer Issa Rae speak on a panel during the Sundance Film Festival on Jan. 25, 2020, at the Blackhouse in Park City, Utah.
Prentice Penny (writer/producer) and Issa RAE (actor/producer), speak during the Sundance Film Festival in Park City on January 25, 2020.
Aaron J. Thornton via Getty Images

That’s evident by the career trajectories of behind-the-camera talent at “Insecure.” Writers Syreeta SingletonAnd Phil Augusta Jackson have inked overall deals with HBO/HBO Max and Universal Television, respectively. Singleton will showrun the upcoming HBO Max series “Rap Sh*t,” while Jackson has created the new series “Grand Crew.” And “Insecure” co-producer Grace Edwards has gone on to create “Jodie,” a spinoff series centering the beloved “Daria” character Jodie Landon.

But sometimes success can come with its own set of issues and unanticipated criticism ― as we see in this season’s fourth episode, when Issa struggles to accommodate white stakeholders while trying to keep the vision of a local Black artist (Kofi Siriboe) authentic.

Penny knows that fans are invested in Issa’s longtime professional dream that has finally manifested this season. Rae and Penny wanted to share the truth about this achievement. “One of the things we wanted to talk about was: What are the problems that come with success? We think we’re just so happy to get there, but it’s also [a] be-careful-what-you-wish-for situation. New levels bring new devils that complicate things.”

It’s a lesson that Penny himself has had to learn. “We have this thing: ′Once we get there, it’ll be fine.′ I used to think that way, because you don’t have a context yet of what that actually means. I’m not saying every person thinks this, but if you’re an actor: ′Oh, I’d love to be at Tom Cruise’s level.′ Well, being Tom Cruise is complicated.”

It’s important for Penny that the same level of sincerity he and Rae put into all other storylines — from what it’s ReallyWould you like to be a 30 something Black woman living in L.A. the complexity of female friendships — matches what they bring to this new narrative. That’s especially significant with Rae’s character encountering new challenges as she ascends through life.

“We wanted to explore when you’re so close to success, and the compromises you have to make, or the way you think you can get into the system,” Penny says. “Do this one thing. The bigger picture is just around the corner. What do I have to do to get to that place?”

Penny no longer grapples with these thoughts himself, but he does spend a lot of time pondering his own legacy — and that of “Insecure.” “I think for me, a big thing is eventually to be able to leave the industry with a stronger pipeline of talent of color than where I found it,” he concludes. “One thing I’m really proud of is getting a lot of directors of color opportunities, breaking some careers and just reinforcing others.”

While Penny was able to promote some of the “Insecure” writers to new positions in the past, he really had to think about how he can support them now that giving them a higher title next season is not an option.

“My big thing was getting them other jobs that they could have on their resume [and] go into their next job,” he says. Just a week before this interview, in fact, he was able to help one of his assistants get his first writer’s assistant position.

“Everybody that was in that writers’ room is a step closer than where they were before they got there,” he says proudly. “The fact that he got his first thing, I felt like, ′Ok, now the hard part is over.’”


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