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Photo Credit: Justin Jackson/truTV

Prentice Penny Talks Three-Dimensional Representation For People Of Color

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Last week truTV launched a new show called “Upscale With Prentice Penny” which airs Tuesday nights at 10pm.

You may not have heard of Prentice Penny before, but it’s highly likely you’ve seen his work. He was a writer for “Girlfriends” and is currently the showrunner for HBO’s hit show “Insecure.” BOSSIP caught up with him to chat about stepping in front of the camera to host “Upscale” — a show that is all about appreciating the finer things in life, whether that means tailored threads, the finest wines or bedding that guarantees an enjoyable nighttime “experience.” Check out our EXCLUSIVE below!

Photo Credit: Justin Jackson/truTV

BOSSIP: Congratulations on stepping in front of the camera! Tell us how “Upscale” came about, did you always plan on hosting?

Prentice Penny: It’s a little bit different. Legit, this was literally some stumbled into something and not realizing until the last minute. I had no plan. It started from an idea my manager and I had. We are big bourbon drinkers and we love barbecue. We were like, ‘We should fly to Kansas City and just try barbecue.’ This was two years ago. Then, we thought, ‘We should film it and put it on YouTube!’ That slowly evolved into whether people of color talk about these kind of things. It never had it’s origin in me being in front of the camera and then I found myself here.

BOSSIP: How did you come up with the different topics for the show?

PP: It started from topics my friends and I actually enjoy. We’ll go smoke cigars, or go try champagne, or talk about steaks. That became the genesis, and so they didn’t feel disconnected we gave them a theme. So the first episode is about romance — so in that topic it became, what kinds of things do you do to incorporate romance into your life? So we talk about bedding, candles and champagne, the clothes you wear when you come to bed, your pajamas etc… Once we gave each show an umbrella, it was ‘Ok, now what are the topics — if it was date night, upscale dressing up and we pitched on ideas I was doing personally and how to incorporate them.

BOSSIP: What do “Insecure” and “Upscale” do to open up the scope of how black people are represented?

PP: “Insecure,” from a scripted standpoint, we’re able to talk about things and see us as fully dimensionalized people who go through things like anyone else. The ideas of being in love and being faithful and trying to find your place in this world are all things we can relate to. For “Upscale,” I was a big fan of “Chef’s Table” and Anthony Bourdain, but my thing was, my friends and I are into these kinds of things, but I don’t see us reflected in these shows, whether they be “Top Chef,” or what have you, you never see us in the forefront of these shows. It’s just like on “Insecure” where we have these conversations all the time, but you just don’t see them onscreen.

I don’t see anyone onscreen doing this, but I do these things and my friends do these things, but it’s always a middle aged white guy speaking as the authority. As the entryway into those worlds, I want to see more of me reflected in those worlds because I do those worlds and people I know do experience those worlds. You rarely see people of color onscreen talking about travel, but we travel all the time. You never see it onscreen.

Photo Credit: Justin Jackson/truTV

For me, it was important to have a ton of people of color come on the show as experts because it was important that it’s reflected in the show. Not even just people of color, but also gender roles. We did an episode where we visited this really cool craft brewery that was run by two women, an Asian woman and a Latina woman and the brewery was in Inglewood. For our date night episode, we talked about manicures and went to a manicure spot that was just for men, that was started by a black man. You go in and the walls are wood, and the chairs are leather, and there’s a big flat screen on the wall and you get scotch when you come in, so it’s to make men feel good. I was like when are you going to see a man talking about manicures onscreen and it’s a straight black man? You’re just not going to see that. That was important to me that we cut against the type and perception, I wanted to upend a lot of that in the show.

Hit the flip for more from Prentice

Photo Credit: Justin Jackson/truTV

Photo Credit: Justin Jackson/truTV


BOSSIP: There is some real classic hip-hop being woven into the background for “Upscale.” Was that something that was done intentionally?

Prentice: 100%. We don’t have a budget like “Insecure” where we can spend a huge amount of money on Solange and Raphael Saadiq, but I have the same music supervisor, so from every aspect, the guests, the way it’s visually shot, the way it sounds, I wanted it to reflect my upbringing. I grew up late 80’s and early 90’s and I always felt when I watch these shows that the music feels like an afterthought. I wanted the music to have a very specific hip-hop sound. Don’t play me any Jamiroquai/jazzy hip-hop sounds. I don’t want to put that music on the show because you have these really beautiful images and the tendency would be to lean into that. If I’m looking at something really beautiful, I want to hear some trap music. That’s what makes it interesting. It’s like when you have the salty and the sweet. You gotta kinda cut it. It was a very cognizant thought to have that feel sonically.

BOSSIP: Is Prentice Penny your real name?

PP: That’s my real name, yes. I hated it growing up, because when you’re a kid you want to be like Chris. You want to go to Disneyland and see your name on the license plates you can buy with your name on it. There was no Prentice cup. I had people calling me Princess, Pringles… The cool thing is it’s paid off as an adult because nobody has that name.

Photo Credit: Justin Jackson/truTV

BOSSIP: What was your favorite episode of “Upscale”?

PP: Just on some cool stuff — the dressing up episode. I got a custom hat made and shoes and a suit. That was cool but on a more personal stylized note. On the human side, the gift giving episode was a favorite. We went to a glass blower and made drinking glasses. What was cool about it is every episode has a payoff in how you incorporate those elements. I did the episode with one of my best friends, my mom and my dad. It was kind of emotional. My best friend really enjoys smoking cigars, so I gave my best friend a cigar. I gave my mom champagne because it reminded me of Christmas when I was a kid, because she would always drink rosé. She was a single mom for the most part and I’m a parent now so I can imagine how hard it must’ve been. For my dad I gave him the glasses. I told him it reminded me of one of the coolest memories I have, which was when my grandfather was still alive and he would let me sit on his lap and it was like three generations together and they would drink bourbon and play dominoes. At the end of the segment I gave my dad the glasses and we played dominoes together. It was just this really human moment.

Hit the flip for more from Prentice on “Insecure” and breaking into Hollywood.

Photo Credit: Justin Jackson/truTV

BOSSIP: We got your favorite “Upscale” moment, what was your favorite “Insecure” moment?

PP: My favorite comedic moment is the opening from the pilot where Issa’s in the classroom and all the kids are dragging her. I think it just encapsulates the show on a basic core level. My favorite dramatic moment is when she and Lawrence, when he confronts her about cheating and walks out on her. Just to watch that scene in real time when Issa and Jay went for it for like eight takes. On set it was emotionally draining to watch and to see it all come together was great.

BOSSIP: What’s the feedback been like from the finale for you?

PP: “Girlfriends” was my first job as a writer and not since then have I had so many people be invested in the characters as real people. Almost anywhere I’m at now, when people who are fans find out what I do they’re like ‘You make me so mad. Oh my God! You people! When he was f***ing Tasha at the end I was so mad. Oh my God.’ But then on the other side, I’ll get the dudes who are like ‘Thank you Bruh, thank you for holding it down.’ It’s so real, it’s like it really happened. Like these are real people in the world. Then you’ll get some women who are really mad at Issa like, ‘There’s chicks out there f***ing it up for us. We can’t find one man and she’s got one and she’s not happy with him.’

When people find out my connection to “Insecure” it’s always, ‘Ooh I need to talk to you!’ That’s always the first reaction. After that I literally don’t know where it’s going to go, if it’s gonna go to Lawrence or Issa or Molly. It’s such a testament to how good the actors are making those characters come to life. It’s also the cultural and political and racial stuff we talk about. That’s real. I go through that. It’s just awesome. Especially in the climate we’re living in right now, that black people can be seen as three-dimensional people and not just caricatures of themselves.

Photo Credit: Justin Jackson/truTV

BOSSIP: What advice do you have for people of color interested in writing for TV or working behind the scenes?

PP: When I was coming up you had to do the traditional route. You write a pilot or a spec script and you hustle to get anyone to read it. You’re trying to get an agent, you’re trying to get a manager. Now, Issa is a testament to all these types of shows where people are doing their own thing. The world we live in now you can shoot your own show digitally and put it up on YouTube and have it live on the web. There’s really no limit. You can do these type of things, you can pursue the traditional way, but in the world we live in now, I wouldn’t wait on nobody. I would grab a camera, I would write 10 episodes. That’s what Issa did. There’s so many outlets digitally that didn’t exist – even more than when she did “Awkward Black Girl.” I always feel like momentum creates more momentum, just by the proxy of doing something more things steam roll. By moving in a direction, other things start to move as well. You can be doing something ten years and nothing happen, you can be doing something a week and something happen. That’s this business. Inevitably things get better because the more you’re doing, the more you’ll improve.

April of last year, I was walking back from the first table read of “Insecure” and my manager called me and told me ‘We sold the show.'[“Upscale] It’s 11 months from when we sold the show to it coming to fruition.I had all the people telling me “he’s never been a host before, there’s never been a market for this show, then we sold the show the fist time out. You gotta just put your head down and go about your business.


BOSSIP: We were super divided in the office about the “Insecure” finale because the guys were very #TeamLawrence and while the ladies weren’t really #TeamIssa there were some who felt she deserved a pass because she was holding him down when he couldn’t pay the bills.

PP: The Issa justifications are so hilarious to me. She handled it the same way men handle cheating. She was just sloppy. She wasn’t good at it because it’s not in her character. She’s not smooth. She’s not a player. She was just in over her head. She did exactly the things guys do so it was funny to hear women try to justify it because guys are just as bad.

Make sure to tune in to truTV tonight at 10pm for “Upscale with Prentice Penny”!

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