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‘Insecure’ Producer Prentice Penny Adjusts to Life in Front of The Camera, Exploring the Good Life for TruTV’s ‘Upscale’

"You never see people of color talk about champagne or travel or wine or cigars," says Penny, who demonstrates how to upgrade to the better things. "But my friends and I do it too."

26551_001 Upscale with Prentice Penny Episode 103 Sex & Romance

Prentice Penny

Justin Jackson

When it came time to host his own TV show, Prentice Penny couldn’t help but feel a little insecure.

Penny hosts the comedic lifestyle series “Upscale with Prentice Penny,” which premieres Tuesday night on TruTV. It’s a bit of an unusual career move for Penny, a writer whose credits include “Happy Endings,” “Brooklyn Nine-Nine,” and “Insecure.”

“I never really thought of myself as a host until we sold it,” Penny said. “And then I was like, ‘woah, shit, now I gotta do this!’ I’m still finding my way, and trying to objectively learn to see myself in a different way.”

“Upscale” follows Penny on an Anthony Bourdain-inspired journey into the world of affordable style. Penny and pals like Adam Pally explore butchers, candle shop owners, tailors and more to demonstrate how anyone can obtain the good things in life.

“It’s a way to upscale things you’re already doing – doing them a tiny bit better,” Penny said. “It’s still you, but an elevated version of you. Growing up, I would just go to the grocery store and get my meat at, say, Ralphs. But I started to be exposed to [ideas like], ‘There’s a butcher? I can get my meat from somebody else?’ I was having those experiences, whether it be wine or travel. And then I found that friends of mine were having these experiences as well.”

READ MORE: ‘Insecure’ Showrunner Prentice Penny on Issa Rae’s Brutally Honest Comedy – IndieWire’s TURN IT ON Podcast

The idea for “Upscale” came from Penny planning a road trip to hit bourbon and barbecue joints across the country. Then someone suggested he film the journey and stick it on YouTube. “It just kept spawning from that germ of an idea to what we have now,” he said. In conversation with his managers, he noted that he was already doing these kinds of things in his personal life.

In the first episode, pegged to “romance,” Penny visits a high-end candle store (“Treat yourself!” Penny says) and enlists ’90s R&B crooner Johnny Gill to sing an original song that pokes fun at the slow jam music videos of the era.

“I wrote this really bad R&B song, and just watched a bunch of ’90s videos and remembered all the tropes,” Penny said. “And I remembered all those Dutch angle shots, and the videos taking place in a room full of candles. We just leaned into those kinds of videos and Johnny was game.”

26551_001 Upscale with Prentice Penny Episode 109 Dressing Up

Prentice Penny

Justin Jackson

In a way, Penny said he was inspired by the themes of “Insecure,” which explores a world not often seen on TV: The friendship between two professional African-American women. Similarly, “when we talk about these worlds, you rarely see a person of color talking about this stuff. But my friends and I are into this stuff – some friends might be into champagne, some might be into golf, but we’re all talking about these things that we never see people of any color reflected in. You never see people of color talk about champagne or travel or wine or cigars. It’s always this sort of middle aged white guy who is, like, ‘This is what you need to do.’ And I was, like, ‘But my friends and I do it too.'”

READ MORE: ‘Upscale with Prentice Penny’ Exclusive Clip: The ‘Insecure’ Showrunner Explores How to Achieve the Good Life

Penny was always going to star on “Upscale” – even though he hadn’t had a lot of on-camera experience in the past. TruTV president Chris Linn said he was sold on “Upscale” exactly because Penny wasn’t an over-rehearsed host.

“Prentice has an incredibly engaging personality which, coupled with his lack of ego in exploring things he knows nothing about, makes you want to go on this journey with him,” Linn said. “It’s something that we noticed immediately in the pitch meeting and has carried through into the series and we’re excited for fans to learn alongside him. It turns out that despite being behind the camera for so long, he’s also really quite funny and comfortable in front of it.”

26551_001 Upscale with Prentice Penny Episode 108 Gift Giving

Prentice Penny

Justin Jackson

Now that he’s back in the writers’ room on “Insecure,” which is in the middle of producing Season 2 (the show resumes shooting on April 3), Penny admits that he’s getting ribbed regularly by his colleagues – particularly now that “Upscale” is being heavily promoted (especially during TruTV’s recent March Madness coverage).

For example, when pancakes were delivered the other day to the “Insecure” writers room, the jokes were immediate: “Oh, do we need some upscale syrup in the room?” Penny says his colleagues have been “super supportive, but they’ve only seen the commercial. In a way I have been waiting, like I’m so nervous and don’t want to be judged, but I know at some point it’s going to be on television and everybody will see.”

At least, with an unscripted series, Penny said he just had to feel comfortable with playing himself.

“It’s weird, but the good thing is that I was doing it every day, for five or six weeks,” he said. “At a certain point you start to find your rhythm, and you start to find what works well and what doesn’t work well. We have a great team who helped me walk through all that stuff, who were protective of me and the show. But still, every time I watch the edit I go, ‘Oh, I’m the worst!'”

Here’s a sneak peek of the first three minutes of “Upscale with Prentice Penny.”

“Upscale with Prentice Penny” airs Tuesdays at 10 p.m. ET on TruTV.

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