‘Insecure’s Prentice Penny Joins Facebook ‘#BuyBlack Friday’ Show: ‘It Felt Like a Natural Connection’

Prentice Penny - BuyBlack Friday
Willy Sanjuan/Invision/AP

Prentice Penny wants to see life imitate art — imitating life — in joining the effort to inspire people to buy from Black-owned businesses this holiday shopping season.

The showrunner and executive producer of “Insecure,” the HBO comedy created by and starring Issa Rae, is among the guests on Friday’s finale of Facebook’s “#BuyBlack Friday,” a series aimed at turning the annual post-Thanksgiving shopping event into a call for consumers to support Black-owned businesses throughout the entire holiday season.

Penny noted that at the end of “Insecure” Season 4, Rae’s character started her own small business as a “cultural curator,” supporting local entrepreneurs, and the next season will build on the exploration of her new undertaking.

“She’s like an event planner, promoting the businesses, not too dissimilar from what this is,” Penny told Variety. About Facebook’s “#BuyBlack Friday” show, he said, “It just felt like a natural connection for me, especially right now given everything going on with COVID.”

Penny said he relates to the struggles of small business owners: When he was growing up, his family owned a furniture store in Compton, Calif. “I can’t imagine what it would be like if we had to deal with COVID,” he said. “My dad’s side of the family, they’re all business owners.”

Having “Insecure” on HBO (and HBO Max) provides a major platform to talk about the Black community “unapologetically” and “organically,” he added. “On ‘Insecure,’ we do a lot to highlight Black businesses — and specifically Black businesses in L.A.”

The finale of “#BuyBlack Friday” will air on Friday, Nov. 27 at 11 a.m. PT on Facebook’s Lift Black Voices hub, as well as the Facebook app and the Facebook page. In addition to Penny, the two-hour special will feature other Black celebrities, musicians, artists and creators including Gabrielle Union, Kawhi Leonard, Marsai Martin, Prentice Penny, Lavonte David, Sloane Stephens, Tiffany R. Warren, Alexis Feacher (@yungbbq), and musical guests DJ D-Nice and Miguel.

Facebook launched “#BuyBlack Friday” given the particular plight of Black-owned businesses in the U.S., which have closed at twice the rate of other businesses due to COVID-19, according to data from the Federal Reserve Bank of New York. “With ‘#BuyBlack Friday,’ our hope is to build a new way people can keep supporting small while many small business storefronts can’t be open,” Facebook says.

Penny, for his part, will speak about “how authentic Black stories get told” on the Facebook show: “Issa talks about love of her community. That’s what people relate to in the show — you have to make sure it feels authentic.”

Rae is also doing her part to promote local shopping: She’s partnered with American Express for its Small Business Saturday campaign on Nov. 28.

Currently, the “Insecure” team is in the writers room on Season 5, aiming to complete the script by Christmas. The next season will “hopefully” start shooting in the new year, Penny said.

Season 5 will not have any COVID-related themes, Penny said, given that it’s set to come out in the fall of 2021. “Are people going to feel like they are be over COVID by next year?” he said, adding that “Insecure” has consistently tried to avoid time-stamping the show with specific references to real-world events.

Meanwhile, Penny is proceeding on several other projects. Those include an untitled Christmas movie for Netflix slated to shoot in 2021. He wrote and made his film directing debut with “Uncorked,” a father-son drama that premiered on Netflix earlier this year.

He also has a film based on the Compton Cowboys in development at Fox Searchlight, and a late-night show with “Saturday Night Live” writer Sam Jay for HBO.

The “#BuyBlack Friday” show was developed by Facebook’s in-house Creative X team. According to Facebook, since “#BuyBlack Friday” debuted Oct. 30, more than 12 million people have watched the show.

The show’s finale has the theme of All Black Everything, about innovators paving their own paths and influencing their industries. The segment will feature a variety of cultural conversations and promote shopping from Black-owned small businesses including Blk & Bold, Mi Cocina, Coco and Breezy Eyewear, Ayond, Earth Tech Surf, and Amalgam Comics and Coffeehouse.