‘Insecure’ Showrunner Prentice Penny on Being in Front of the Camera for His Unscripted Series ‘Upscale’

On the new TruTV show, Penny offers up advice and instruction on how to "upscale your life"

26551_001 Upscale with Prentice Penny Episode
Justin Jackson

“Insecure” showrunner Prentice Penny swears up, down, and sideways that he never intended to be in front of the camera — the former “Happy Endings” and “Brooklyn Nine-Nine” writer has been very happy writing comedy behind-the-scenes. But as he explained to Variety, becoming successful meant learning how to buy things better. “Upscale with Prentice Penny,” debuting Tuesday, Mar. 21 on TruTV, is an unscripted tutorial on how to be a more conscious consumer — with an eye toward luxury, quality, good taste, and the finer things in life. In the first episode, Penny uses a (fictional) cheesy R&B music video from the ’90s as inspiration to upscale his date night, which leads him to search for better bedsheets, a nicer evening robe, quality champagne, and a couple of candles to set the mood. (He never does reveal if his wife went for his efforts, but he probably wouldn’t have been in such good spirits when we talked if she hadn’t.) Below, Penny talks why he wanted to make “Upscale,” what he hopes audiences of color will get from the series, and the one thing Issa Rae always writes herself on “Insecure,” no matter how much the rest of the writers know her voice.

In the opening of “Upscale,” you talk a little bit about how growing up, you never thought you’d be able to afford the types of things you can now. 

For me, it was just like — being a [TV] writer, I was just exposed to more. I grew up like a lot of us: You wanted meat, you went to the grocery store. Obviously, I still do all the time, you know what I mean. But as I was getting exposed to other things, it was like, oh, you can go to Trader Joe’s, or you can go to Whole Foods, or wait, there’s a butcher? And I can go, it’s just meat. I would think those things would be super expensive — and then I was like, wait, it’s like two dollars more than what I get at the grocery, but it’s like 10 times better. I was finding that across the board in lots of different areas of my life.   

That’s really just how it started. That started happening for me about 10 years ago — before then, I was a substitute teacher. When I learned is, it’s not about the money, it’s just about having information, and being knowledgeable, and being exposed to more. That’s what it really was about. What I never wanted to do was feel like the show is subjective, where it’s like, oh, you need to get the hot whatever, because it’s not about that. I wanted the show to feel more objective than subjective. It’s like: you may not like the wine I like, or you may not like the whatever I like, but you can go and just explore the world. Because sometimes we’re just afraid to ask questions.

Were you seeing other people around you feel things like this, too?

Yeah. I mean, I think we were all coming of the age where like, my friends and I were starting to do a little better, obviously out of college, financially. And beyond the financial part, I think we were just growing up into grown-ups. At a certain point you got to do your big boy stuff, you got to get a big boy watch, you got to get big boy furniture. Your suits have to start fitting correctly. You can’t just do those things you just do as a kid.

I’m a big fan of [Anthony] Bourdain, and [Netflix docuseries] “Chef’s Table,” but my thing was — as a person of color, usually when I watch shows in that world I don’t see anybody that reflects me, or reflected my friends, or reflected people I knew in lots of different cultures. Sort of felt like there was this middle-aged white guy, sitting there and telling me the authority on fashion, wine, stuff like that. I was just like: Obviously my friends and I do this, I watch us do this, but there’s nobody talking to that to me and of my generation to do that. It felt like a thing that I was looking at in my personal life. If I wasn’t doing this in my personal life, there wouldn’t be a show. Do you know what I mean?   

This show is my life, and how I grew up is in all the ways the show opens. The first episode opens on a bad ’90s R&B music video with Johnny Gill, the musician. Some episodes have flashbacks. Some episodes have a puppet, that’s like a puppet version of myself, a puppet apprentice who’s kind of pathetic. We have animated openings. We have flashback openings. We have a storybook, like a children’s book opening. We have like an old ’70s airline ad as a travel opening thing. So much of my life is reflected in the show.

A lot of that consumer consciousness, or product consciousness, is classed information. It’s interesting that your show is kind of a guide for people to learn what it’s like to appreciate these things, or to be comfortable with having so many resources, that you can start to be more discerning.   

There were a couple things in the show that really had nothing to do with money. We did a whole episode on how to upscale your date nights. A lot of us, we find ourselves in situations where we’ve been in relationships for a long time, we kind of just take it for granted. How do you upscale that? We went to a thing where we talked to an etiquette expert, and we did a segment on etiquette, which has nothing to do with money. It has to do with how you treat somebody, the proper way to do that stuff. We did a segment on there that was about calligraphy — but really what it was about was like how to personalize, or make your invite more formal. Just like writing a note, it’s just like writing a letter as the invite instead of texting what you’re doing. A bunch of the things we do literally sometimes have nothing to do with, oh, it’s about money. Sometimes, again, it’s just about knowing that you can do better — and how you do that most days. It doesn’t always correlate to a dollar amount. Sometimes it’s actually less money than probably what you’re spending out there now.

Another [segment] we did was about gift giving, where we had to give somebody a bottle of wine. You’re still buying a bottle of wine. It’s not about the money, you’re still going to do it. but it’s just knowing. It’s knowing there’s a different way to do and a different way to approach it. That’s what I mean when I say, “It’s not always about money, or you’re already doing these things in your life anyway.” You don’t have to overextend yourself in this way, it’s just upscaling when you think about those things. Sometimes it’s a state of mind, sometimes it’s an actual dollar amount, but I think it’s a way that we can all sort of live our lives just a little bit better.   

How did you come to the point where you wanted to host your own show?

I never set out to ever — I mean literally ever be in front of the camera. That was no goal of mine, ever. I’ve just been a television writer and fine, happy doing that. But that’s it: I was doing these things at home normally, getting into them. Literally, the idea just stemmed from one of my producers and I just talking about it two years ago. We’re big bourbon and barbecue guys, and we were like, we should just fly to Kansas City, live in an RV for two weeks, and just try barbecues. That’s literally how basic — and it wasn’t even a TV show, it was just us as friends. And then it segued into, well, we just film it, just for, we can show our kids one day. Then it was like, we can film it and maybe eat a like, post about little barbecue places we go, on YouTube. Over two years, that initial idea kind of evolved. And again, I was saying that I don’t really see anybody of my generation doing this, and certainly not people of color or world that reflects the world we sort of live in. Those two ideas kind of melded into “Upscale,” and two years later, here we are.

I love Bourdain, and stuff like that, and [Andrew] Zimmern. They’re great, and they’re great voyeuristically. But I also know I’m a father of three; I can’t go to a little village in Thailand, or wherever, and try this amazing foie gras. [Laughs.] I just don’t have the time! But what I can do is I can go to a wine thing and buy a bottle of champagne that I didn’t think about before. I can go to the butcher and get a nice steak. I can go to the tailor and get a suit made and spend basically what I’m going to spend in the store, but it’s going to be made for me.

Those are the things I was trying to do — make it feel more relatable as something that you could actually live your life and do. Bourdain’s stuff is great, because you’re like, oh, that’s cool, I’ll never get to go there. It’s cool I get to see it. But see, I wanted people to have the same experience I was having. The real awakening that I was having, too. I was always thought only rappers or athletes got their suits made, and I didn’t know — it’s totally doable. And what’s funny, is we get to like — we go to a shoe cobbler, we can go to a tailor, we can got to all these places, and talk with peers. It’s funny, because every person would inevitably say, this is the way we used to live our lives. We used to go to a butcher. We used to go to a tailor. Now in the wake of malls, and big box chains and stores, we obviously live differently. But not too long ago, this is all you did. It’s kind of nice to get back to those things, because you start to develop relationships with these people that can open you up to even more things. That’s the stuff that I thought was really cool.

A lot of “Insecure” is also about navigating different cultures and classes. It’s very fitting that “Upscale,” in a different and more instructive way, deals with some of the same ideas.

Yeah it is. It’s so funny, I don’t know if would’ve done “Upscale” the way I did had I not had my experience on “Insecure.” In many ways — like in making sure the world feels diverse and interesting. We had everybody — black, white, Asian, Latino, all throughout “Upscale.” But one of the things that’s also important was cutting against types. We did an episode about summertime — so barbecue, ice cream, all this stuff in there. But one of the other segments was about beer, about how to upscale up to craft beer, something like that. The cool thing was — we found a brewery that was run by two women, which you don’t typically see or think of when you think of the world of beer. They’re brewing up in Inglewood, California. It was amazing.

Contrary to that, we did an episode about date night, we did an episode about getting a manicure. And we found an African-American man who had a manicure spot that’s just for men. Leather chairs, wood walls, and you got a glass of scotch, or beer, or wine when you walked in, and it was just for men. We were trying to also shake things up in terms of the people giving the information, so it’s like, everybody’s comfortable with it.

Even the way we approached the show visually from ‘Insecure’, in terms of having like, making everything feel purposeful. Sometimes I feel like when I watch shows in that world — I feel like they kind of just feel like they just grabbed a camera and just started filming something. I wanted the show to feel cinematic in a way. Our approach was like, if Wes Anderson was going to go a lifestyle show, what might it look like? We wanted things to sometimes feel very portraiture, and very composed, and very visually incorporated. That to me was a fun style to do a show in, and that I felt like I hadn’t seen before. Everything in “Upscale” is very conscious.

You’re doing narration for this show because you’re the host — and while, of course, in “Insecure,” Issa Rae is a real person who narrates, I do feel there are these similarities between the character’s voice and yours in this show. You call some bedsheets “hella plush” in the first episode, and I feel that Issa might say that, too.

That’s a very LA thing. Issa and I are both from LA. It’s a super LA thing to do. [Laughs.]

I mean, [on “Insecure,”] we all do [Issa’s narration] as a staff. The one thing that Issa does that nobody on the show does are the raps. When she’s rapping in the mirror, we just always put “rap TBD.” Nobody can do that like her. None of us, me included, could ever write them like she does, because it’s the most subjective part of our show, and she does them so great. I don’t anybody could copy it, anybody would want to try to copy it, or try to make an attempt at it, because she’s just so good at it.

It’s a very — when you’re on the show and you have somebody’s who’s obviously the star and the creator, the show is always in their voice, but obviously you have other writers who do that, who also obviously write the show. That’s why I kind of love it. That’s the one part of this show that no matter how much she shares, it’s kind of hers as a creator, which I just think is so cool and interesting. But I kind of love that part of the show will always be hers. I think it’s kind of sweet.