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From ‘Insecure’ to ‘Upscale’ With Bright Talent

Showrunner Prentice Penny makes move to unscripted, and new opportunities 3/27/2017 8:00 AM Eastern

Prentice Penny, showrunner for HBO’s freshman comedy series Insecure, steps out in front of the camera for his new truTV unscripted series Upscale With Prentice Penny. The series, which launched March 22, follows Penny as he upgrades his life to experience the finer things in travel, cuisine and fashion. Penny, who also counts in his production credits stints at Fox’s Brooklyn Nine-Nine and NBC’s Scrubs, spoke with Multichannel News programming editor R. Thomas Umstead about the challenges of developing unscripted content and the opportunities new digital distribution platforms have opened up for writers and producers of color to get their projects in front of millions of potential viewers. An edited transcript of the interview follows.

MCN: You’ve worked on a lot of scripted shows in the past, so was Upscale a different challenge for you?
Prentice Penny: Obviously being in front of the camera, it’s much different. I was telling somebody that after my first day I had a whole new respect for Ryan Seacrest because he makes it look so easy, as if anybody can do that, and really everybody can’t do that. So it’s been challenging in terms of just becoming more and more comfortable being in front of the camera, but it’s been fun. With scripted you’re constantly thinking about a story, whereas with [unscripted] there’s also a story, but in a different way.

MCN: You’ve mentioned in the past that Upscale is a passion project for you. Why was truTV the best network for your show?
PP: Really, it was just the freedom of trust. I’ve worked in network television a long time and there are times when everybody wants to go to the right and there are too many chefs fiddling with the formula. Sometimes you have to let the show be the show. What’s been great about truTV is they said, “What are you interested in doing?” and then were supportive of that vision. The most free part is being OK to try something that maybe works or maybe doesn’t work. They’ve just been so collaborative in allowing me to make the best version of the show and that’s been great.

MCN: You’ve been on a roll with successful scripted series, including HBO’s Insecure. Were you surprised by the show’s success?
PP: I’m constantly surprised and I feel blessed. There’s no formula for success. I’ve been on projects where people have said this show’s going to go on forever, and it goes two weeks. You have no idea what people are going to respond to, so I just feel blessed that people responded to Insecure and liked it. You just try to do the best version of your show. You can’t control the viewing public, and you can’t decide what they watch. So you just have to do the best you can do and focus on the work and the other stuff kind of falls into place.

MCN: Given the success of Insecure and of other diversity-themed content, is now a great time for people of color to get their projects distributed, given the multitude of content distribution companies across multiple platforms?
PP: The truth is I have no idea. I hope that lots of voices can get heard. I will say that with the creation of the digital space, people can just make their own content, put it out and connect with people right away; it definitely changes the way content gets to the marketplace. So I think that definitely opens a door for literally anybody that has something to say, which really represents [Insecure star/creator] Issa [Rae]. I think the web and YouTube definitely helps infuse a world of diverse talent that normally might not have had that same avenue in the old days.

MCN: What’s on your DVR?
PP: I definitely try to squeeze television in for sure. I still love movies and I love [Netflix’s supernatural drama] Stranger Things. I loved the O.J. Simpson shows — stuff that I had to watch because I didn’t want to miss it. It felt like fun things to see.

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