Prentice Penny

‘Insecure’ Showrunner Prentice Penny Wants to Help ‘Upscale’ Your Life

On his new TV show, the writer and producer is teaching viewers how to live an elevated life, no matter their budget

Prentice Penny

"Upscale with Prentice Penny" Episode 108 Gift Giving

After landing his first job on a TV show back in 2004, writer and producer Prentice Penny found out there was a whole other world full of designer scarves, tailored suits, and fine cuts of meat he knew nothing about.

“I was barely making any money, but when I got on Girlfriends I was exposed to people who were financially doing better,” he tells EBONY.



The experience changed his entire outlook on life. “I was being exposed to more and different stuff, then being like, why do I have to go to the grocery store, why can’t I go to the butcher? Why can’t I go to a shoe cobbler to get my shoes re-soled instead of buying more ones. I just didn’t know, so that’s how it got started.”

Penny, who’s written and produced on shows like Scrubs, Happy Endings, and Brooklyn Nine-Nine, started to “upscale” his life in little ways long before it became the premise of his new TruTV show, Upscale with Prentice Penny. Now, he’s hoping to help viewers upgrade their lives across the board.

Each week on Upscale, Penny will show viewers what it takes to treat themselves, and others, to an elevated life. From picking the best wine to suit individual tastes, to getting a custom-made suit for less than some off-the-rack options, Upscale with Prentice Penny will show fans how to make their lives just a little bit better, no matter their income.

“Sometimes the thing we’re upscaling is how you think; they don’t have a financial dollar attached to it,” he explains. “Upscaling, to me, is about having information. If you know more, you can do more and have more choices available to you.”

While Penny learned quite a bit over the years about taking his life to the next level, the husband and father said the show has had a lasting impact on his family. After filming an episode about dressing up and learning the history of why some suit jackets have buttons on the sleeves–because doctors would sometimes need to roll of their sleeves during an emergency–he was able to share that knowledge with his kids.

“When I talk to my two boys, I’m able to teach them things I didn’t learn until I was 30,” he says. “When I see my son now, who before would go tuck his shirt in without looking to see if he’s looking all crazy, now when I watch him go into the bathroom and make sure his clothes look nice in the mirror, that feels good. There’s no level of upscaleness that tops that to me.”

As with HBO’s Insecure, on which Penny serves as showrunner, it was important for Upscale to reflect the diversity of our world.

“It was important for us to have a ton of people of color and have our experts look like America,” he explains. “We did a segment on beer, and we did a segment on two women–Asian and Hispanic–who run a brewery in Inglewood. We did an episode on manicures, and we had an African-American man who has a manicure spot for men. So you typically don’t see that, but it was important to have this show reflect the world in which we live.”

He adds, “Hopefully we’re upscaling not just the things we’re talking about, but the way we see people who are trying to upscale your life as well.”

Upscale with Prentice Penny airs Tuesdays at 10pm on TruTV





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