Prentice Penny Swaps Politeness for Public Embarrassment

The "Insecure" showrunner shares how "Upscale with Prentice Penny" can improve our lives, before helping our listeners deal with friends who send too many texts and misuse "shade."

(Photo Credit: Charley Gallay/Getty Images for truTV )

Each week you send us your questions about how to behave, and here to answer them this time around is Prentice Penny.

He’s the showrunner for HBO’s Golden Globe-nominated series “Insecure.” He also wrote for network comedy shows like “Brooklyn Nine-Nine,” “Scrubs,” and “Happy Endings.” And on his new show, he steps in front of the camera.

The show is called “Upscale with Prentice Penny.” He learns how to live the good life, from how to make a perfect burger to how to pick a perfect suit. Which made him a solid choice to answer our listeners’ etiquette questions.



Brendan Francis Newnam: We’re so happy you’re here, but we have to say, we thought we had the greatest job, where we get to talk to smart people and eat good food, but you really have the greatest job.

Rico Gagliano: Yeah. Was the pitch, “I want to get nice stuff?”

Prentice Penny: The pitch was: how do I just do baller stuff?

Rico Gagliano: Good job.

Prentice Penny: Can I get $8 million to just basically drink champagne?

Rico Gagliano: We have to address the elephant in the room. There’s this huge political discussion going on right now about income inequality, haves and have-nots. Here you are with this show celebrating upscale living. How does it fit with the times?

Prentice Penny: Well, really, the interesting thing about the show — it’s not about money, right? It’s just about, sometimes, having information and just doing better.

So, for example, I grew up, like a lot of us, we just go to the grocery store, grab some hamburger meat, go home, make hamburgers, that’s kind of it. Or just grab some American cheese and blah, blah, blah, you’re done. I had never heard of a Whole Foods up until 10 years ago. I was like, “What’s that?”

But you just have to learn about, like, I can go get a steak from a butcher that’s a couple of bucks more, but the quality of all that stuff is going to be a million times better. And I learned it had nothing to do with money. Sometimes the prices are comparable.

It’s like, you’re already buying a bottle of wine, right? But it’s just knowing, maybe, more about how wine is made and what fits your palate. So, actually, sometimes it helps you on the money side because you’re not feeling like you have to spend a bunch of money to get better quality stuff.

Rico Gagliano: I can think of a few other TV showrunners who have made the move in front of the camera. Larry David is one of them. Larry Wilmore, maybe, is another. They’re all named Larry for some reason. I’m wondering…

Brendan Francis Newnam: Yeah, you’re the first non-Larry, Prentice. Well done.

Prentice Penny: Yeah. I’m making it. I’m. Making. It.

Rico Gagliano: You’re changing the paradigm.

Prentice Penny: Here we go.

Rico Gagliano: What maybe surprised you about being on camera?

Prentice Penny: What really surprised me was, you know, you see guys like Mario Lopez and Ryan Seacrest, and you’re just like, “They seem cheesy.” You’re like, “That’s not a job.” You’re just, like, “Whatever.” And when you have to do it…

Rico Gagliano: It’s hard.

Prentice Penny: It’s hard! It seems like it’s not hard. It’s hard.

Rico Gagliano: What was the hardest thing for you?

Prentice Penny: Here was the hard thing that I had to learn: I had to learn to experience the moment because I’m used to being on set, and after we’ll say a line, and I’m scribbling the note of, like, “I want to change this,” or “I have a pitch on this joke right now.”

And I was talking with people, they’d say something funny or do something, and I was thinking of the bit that I could do or thinking of response. Thinking too much and not experiencing the thing. I just learned to start having conversations, which, weirdly, in our culture right now, people rarely have conversations.

Brendan Francis Newnam: Well, I was going to say, now you can empathize with how I was only half-listening to you just then.

Prentice Penny: I totally get it.

Brendan Francis Newnam: I was listening to you, but I was also looking ahead about how we can transition to our etiquette questions.

Prentice Penny: Come on, I’m married. I’m used to that. I’m used to being half-listened to.

Brendan Francis Newnam: All right, so then, are you ready for our listeners’ questions?

Prentice Penny: I’m ready.

Rico Gagliano: That was a good segue.

Prentice Penny: That was a good segue!

The Hummer of the cigarette world

Brendan Francis Newnam: So, this first question comes from J.R. in L.A., and the question is: “I like the smell of cigars in moderation, but they are so pungent up close. How much space should a cigar smoker put between him or herself and unsuspecting bystanders, say, at a park?”

Prentice Penny: There’s lots of things happening there. First off, it seems like you don’t like cigars.

Rico Gagliano: Well, he likes the smell of them.

Prentice Penny: He likes the smell. Well, that’s a tricky thing.

Rico Gagliano: But not up close.

Prentice Penny: Not up close. So, is he smoking them in this situation, or he’s saying other people are smoking?

Brendan Francis Newnam: I think other people are smoking them nearby.

Prentice Penny: I would say: take your left leg, take a step; take your right leg, take a step; and keep stepping until you no longer smell the cigars.

Rico Gagliano: But I think the question then is, is it his responsibility to do that? He’s not the smoker. He’s an innocent bystander.

Prentice Penny: He’s just chilling there. He’s just chilling.

Rico Gagliano: Wandering through the park.

Prentice Penny: Just keep wandering, man. Just keep wandering.

Brendan Francis Newnam: I know, park’s tough.

Prentice Penny: It’s tough.

Brendan Francis Newnam: Because I don’t like secondhand smoke, but a park is an area outside.

Rico Gagliano: Actually, though, I don’t even know. Here in California, are parks off-limits to smoking? Could you call the police?

Prentice Penny: It’s constantly changing. I don’t know. Everything is– it’s changing so fast!

Brendan Francis Newnam: I will say, but cigars — let’s be honest — cigars are the tractor trailers of the cigarette kingdom. They’re huge.

Prentice Penny: They are.

Brendan Francis Newnam: They pollute, and don’t you get the sense when you walk behind someone smoking a cigar that they know that they’re annoying everyone? It feels a little…

Prentice Penny: But if I think about how much he spent on that cigar, god bless you. Smoke that thing. That thing could’ve cost $25.

Rico Gagliano: Isn’t that even worse? You’ve got this expensive thing, and you’re just showing off how terrible you can make life for everyone else with it.

Prentice Penny: He’s still driving a Hummer. He’s still driving a Hummer.

Rico Gagliano: Yeah, it’s more like the Hummer.

Brendan Francis Newnam: It is the Hummer of the cigarette world. That’s a good point.

Rico Gagliano: Exactly.

Brendan Francis Newnam: But you know what? You should be able to drive your Hummer anywhere you want in the park.

Prentice Penny: I agree. If you pony that thing up, and you’re paying for the gas…

Rico Gagliano: Certainly in America, that seems to be OK. So, there you go, J.R. I guess this…

Prentice Penny: Just keep walking, man.

Too many texts

Rico Gagliano: Here’s something from Maya in Henderson, Nevada. And Maya asks: “My friend always sends me seven little text messages when one big one would do.”

Prentice Penny: That’s so real.

Rico Gagliano: “It is”–in all caps– “SO ANNOYING!!!” “I have stopped responding to her, but I think I need a better strategy for letting her know it bugs me.”

Brendan Francis Newnam: Whoa.

Rico Gagliano: Something better than passive aggression.

Brendan Francis Newnam: Maya’s tough.

Prentice Penny: I would say your best thing would be: send eight little texts saying all the ways sending seven little texts is annoying.

Rico Gagliano: Yeah, one word in each text.

Prentice Penny: And one word, period, in each text.

Rico Gagliano: Yeah. You’re generating empathy by doing that.

Prentice Penny: Yes.

Brendan Francis Newnam: I’ll say this, though: sometimes you send short text messages to let people know that you’re communicating with them, as opposed to taking time to draw up one long text.

Rico Gagliano: They’re trying to engage you in a conversation, rather than just bombarding you with info.

Brendan Francis Newnam: That’s right.

Prentice Penny: Right, but I do think, once you get past four texts and the person hasn’t responded, it’s like, chill out.

Rico Gagliano: Take a break.

Prentice Penny: Chill out. Chill out. Maybe they’re doing something.

Rico Gagliano: Maya, I think you got your answer.

Brendan Francis Newnam: That’s etiquette.

When slang appropriation goes wrong

Rico Gagliano: Here’s something from Andy in Chicago, Illinois. Andy writes: “I have a coworker who frequently misuses slang terms.”

Prentice Penny: This is going to be bad.

Rico Gagliano: “Words like ‘shade‘ and even ‘ratchet.’ How do I even tell her that she’s not using these words correctly? Should I sit her down and educate her? Or just let her continue to do her thing?”

Prentice Penny: First off, I’m going to guess that both those people are white. How about I just go out on a limb and say… for sure, the person saying the terms is white. I know that.

Rico Gagliano: Yes, “I heard this on a show.”

Prentice Penny: “I saw ‘Insecure’ and I watch ‘Atlanta.’ I saw 20 minutes of ‘Queen Sugar,’ and I know something.”

Rico Gagliano: “I’m going to deploy these words now.”

Prentice Penny: “I want to drop these things.”

Brendan Francis Newnam: “Stop throwing Venetian blinds at me! I mean shade.”

Rico Gagliano: “Isn’t that right?” So, what does Andy do?

Prentice Penny: You know what? I always feel the best thing is letting them get publicly embarrassed.

So, I would find a situation in which I would bring around a person of color and not get them to say it, but make them feel comfortable that they can say it, and then watch them be embarrassed because that’s almost the best teacher.

That’s like my kids. I think they’re only going to learn if they break their arm. If you tell them, “Don’t jump off the fence,” they’re going to not listen. She might need to get slapped at work. It just might need to happen. It just might need to happen.

Rico Gagliano: Isn’t that a little cowardly, though? You’re now going to foist this responsibility off on your friend.

Brendan Francis Newnam: Rico, this is from a man who breaks his children’s limbs to teach them lessons. So, I don’t think he’s worried about cowardly.

Rico Gagliano: Yep, I guess we got the answer we deserved.

Brendan Francis Newnam: Well, Andy, perhaps that answer is too ratchet for you, but let us know how it works out. Do not throw shade on our dear program. Prentice, thanks so much for telling our audience how to behave.

Prentice Penny: You’re welcome, man.