'Insecure' Showrunner Prentice Penny : It's Been a Minute with Sam Sanders Prentice Penny, showrunner for 'Insecure', joins Sam to talk about the HBO comedy series, which just wrapped its second season. They also discuss what a showrunner does, how he got the job, collaborating with star and co-creator Issa Rae, diversity in television, why he likes Drake (and Sam doesn't), how he came to love television and writing as a kid, how he almost became a marine biologist, and black Twitter. Email the show at samsanders@npr.org and follow Sam on Twitter @samsanders.
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'Insecure' Showrunner Prentice Penny

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'Insecure' Showrunner Prentice Penny

'Insecure' Showrunner Prentice Penny

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Hey, y'all, Sam Sanders here. IT'S BEEN A MINUTE. For today's deep dive, we're talking with someone at the top of his game from the world of television - Prentice Penny, showrunner for HBO's "Insecure." "Insecure" is this comedy series that just wrapped its second season this summer. Its star and co-creator is Issa Rae - may've heard of her. She plays the 29-year-old woman in the show whose life is just kind of stalled, and she's trying to figure out dating, and relationships, and identity, and race, and work stuff and just being kind of awkward.

If you're not watching this show, trust me, you should be. But there's no need to watch the show to enjoy this conversation. Prentice and I cover TV, Emmys, diversity in Hollywood, what a showrunner actually does, how Prentice became a showrunner and why, five years ago, no one was talking about showrunners at all. All of that's in the conversation.

Also a bit of background - Prentice has been in the industry for a while. Before "Insecure," he was a writer for TV and a producer on the Fox sitcom "Brooklyn Nine-Nine." He wrote for literally my favorite sitcom of all time, "Happy Endings" on ABC. And he worked on a really classic show called "Girlfriends," this UPN sitcom from the early 2000s - hugely underrated. Also, like "Insecure," that show was about strong black women trying to figure things out. Anyway, we go there, talk about all of that. And we also have a small fight about Drake. I know. All right, here's me talking to Prentice Penny. I was here in D.C. He was in L.A. We taped this just a couple of days after the Emmy Awards. All right, enjoy.


SANDERS: I've seen enough of you on the Internet. You dress snazzy. You've got a fresh taper. You keep it together every day. That's work. How do you commit to that? Because I can't.

PRENTICE PENNY: I - you know, it's so weird. Like, I have always been like that, so it's almost - like, right now, I'm so bummy (ph) today when, like...

SANDERS: Well, OK, but, like, what's bummy (ph) for you? Like, what - like...

PENNY: No, this is pretty cool. I'm going to the gym right afterwards. So I'm actually, like, in, like, sweats and, like, something I would, like - if you were here in person, I would not dress this way, even if I was going to the gym. So I would still...

SANDERS: But they're probably, like, designer sweat though, right? Don't lie.

PENNY: No, they're the most basic Champion, no-name-brand, Ross Dress For Less sweats.

SANDERS: (Laughter) OK, speaking of how you looked - were you wearing a tuxedo on Sunday at the Emmys? Were you there?

PENNY: No, I wasn't. Well, we weren't nominated, so I wasn't actually at the event. Although, I know Issa was there.

SANDERS: Issa was there, yeah, looking sharp.

PENNY: And I got - obviously, I got invited to a party or two. But, you know, it was - it's weird because, you know, the Emmys are over at 8 - or at least 8 o'clock, you know, West Coast time. And, you know, I got kids. I got three kids, and we got school the next day.

SANDERS: I hear you.

PENNY: And we weren't nominated. And I don't think the thought of, like - and I've done - I've gone to a few parties like that. And the thought of, like, getting dressed up at, like, 8 o'clock to go to a party to drink, to know that I got to wake up at 6 o'clock to get my kids up for school was just like, not. And I've been super busy with the show, so I - you know, I've been trying to spend as much family time as possible before I go back to work. So nah, I just stay at the house. I had a couple drinks at the house and watched it.

SANDERS: So three kids - how old are they?

PENNY: Three - my oldest is a couple of months away from being 10. And then my twins, who are boy, girl, are 7.

SANDERS: That's a lot of kids.

PENNY: It's a lot of kids, man.


SANDERS: So you watched the Emmys. Two - at least two folks that you know well had some fun moments. I enjoyed watching Lena Waithe win.

PENNY: So happy for Lena.

SANDERS: You know, I interviewed her on this show a while back, and she's the sweetest.

PENNY: Oh, really?

SANDERS: Yeah. We talked, gosh, about an hour and a half. And I was like, I don't want you to leave. I love you so much.

PENNY: Nah, she's the best. I love Lena.

SANDERS: Well, and then someone who you work closely with right now, Issa Rae, had a moment on the red carpet.

PENNY: Yes (laughter).

SANDERS: ...That started some chatter.

PENNY: I loved that.

SANDERS: For those listening that haven't heard, when asked on the red carpet who she was supporting to win awards that night at the Emmys, Issa replied - what'd she say? - all the black ones.

PENNY: All the black people (laughter).

SANDERS: All the black people. How'd you feel about that?

PENNY: I loved it. I mean, like - I mean, one, it's like, you know, she's a comedy person. So it was, like - it's a part - part of it's a joke. And then, like, part of it's also real. It's like, we don't really always get moments to be nominated. And so, like, it's no different than black people who were pulling for Obama or when - I remember when I was a kid watching the Super Bowl, and Doug Williams was in the Super Bowl. You, like - you want the black quarterback to win. You want to feel like, yes, we can compete on the same playing field across all areas.

SANDERS: Platforms, yeah.

PENNY: ...As our contemporaries. And so, yeah, like, you - of course you do.

SANDERS: Yeah, you know, it's interesting. You know, like, Sunday night was a night of validation for a lot of people of color - you know, Donald Glover winning twice, Riz Ahmed winning, Sterling K. Brown winning - I mean, such support for your show "Insecure" - like, this seems like a very specific moment specifically for TV made for and by people of color. What made everything happen, and kind of at the same time, it feels like?

PENNY: I mean, I don't know. You know, I mean obviously, you know, we're not involved with what Atlanta's doing and, you know. But I definitely feel like that the absence of it for so long was, like, hey, where - where are we? I feel like while I was, like, working on - on mainstream shows where I was the only person of color in the room, or the only - certainly the only African-American person in the room, like, Issa was incubating and seeing that and being like, well, let me - I want to do something that represents me. Like, when I left "Girlfriends,"...

SANDERS: Also, slide bar snaps for "Girlfriends."

PENNY: There we go.

SANDERS: Love that show, too.

PENNY: That's what's up. That's what's up. But after - like, when I left "Girlfriends," after - that was '07, during the writers' strike, I didn't work with another person of color until - I mean, another black person - until "Insecure" in 2015. So you're talking, like...


PENNY: ...I worked on every other show I worked on, and I'm very happy to have those opportunities, but I was the only African-American person in the writers' room. And - and a lot of the shows were being canceled at the same time. So you're talking eight years, or seven, seven, eight years of not seeing anybody who looks like you on network television unless they are, like, in an ensemble drama on CBS or...

SANDERS: Yeah. Doing some Shonda stuff.

PENNY: ...Or whatever. Yeah.

SANDERS: Yeah. Yeah.

PENNY: Yeah. So I just think, like, people were - after a while, it's like, it took, like, those eight years - seven, eight years for people to be like, hey, I want to see myself, you know?

SANDERS: Yeah. Well, and, you know, what I found really interesting when I talked with Lena, it was almost as if there was this, like, Underground Railroad of black folks in the industry, like, helping each other get that next gig, get that chance, get that shot. And she talked about this litany, almost, of black women that gave her shots and chances that other folks wouldn't. And I was reading about the way you got with "Insecure." You basically made your train on that railroad yourself. Like, you wrote Issa Rae out of the blue and were like, you need me on your show. Talk about that. How'd that happen?

PENNY: Yeah. I didn't say you need me.


SANDERS: What'd you say? But you did, like, write her out of the blue and were like, hey, what's up?

PENNY: Yeah. What happened was, I was on "Brooklyn Nine-Nine..."

SANDERS: What happened was (laughter).

PENNY: (Unintelligible). Like, you need me, girl.

SANDERS: (Laughter). This is what you need.

PENNY: Yeah, it's what you need in your life. Get me in your life.

SANDERS: (Laughter).

PENNY: But, no, like, I - I was on "Brooklyn Nine-Nine."

SANDERS: Also a great show. You're always around great shows.

PENNY: I'm just very thankful that smart people have given me opportunities, for sure.


PENNY: But I saw that the show got picked up to go to a pilot and...

SANDERS: That "Insecure" got picked up.

PENNY: ...This was, like, February of - January maybe-ish, February of 2015, and that they needed a showrunner because Larry Wilmore, who had - who was obviously going to be the showrunner with her, got his - his nightly show on Comedy Central so he couldn't do both duties. And they needed a - they were going to be - they were like, the showrunner search is about to begin. And so I was like, OK. So I emailed my agent and was like, yo, get me an interview to run this show. And just...

SANDERS: Had you run a show before?

PENNY: I had run a show, my own show, on this network called Fuse around 2012 called "The Hustle."


PENNY: Which, weirdly, the two leads of that show were Y'lan Noel, who ends up playing Daniel on our show, and this guy named London Brown, who is also Reggie on "Ballers." So it's so weird that we're all now on HBO and we had done this little - so it was on Fuse, and it was, like, a hip-hop entourage. It was, like, a six-episode show and...


PENNY: It was - Fuse was trying to get into scripted, and...


PENNY: But it was the time I got to hire my own writing staff and run a show and do all that stuff. So I had done that. And then so I emailed my agent, was, like, hey, get me a meeting. And it was a blessing that one of the agents at CAA, who's now at William Morris, Ashley Holland, was like, I went to college with Issa. I know Issa very well, and why don't you write her a letter - 'cause I didn't know Issa - why don't you write her a letter about, like, why you think you guys would be a good fit - why you need me?

SANDERS: Did you write it or type it? Why you need me. Did you write?

PENNY: I mean, I wrote it free. I mean, I typed it eventually, but I wrote it as a free-hand thing. So I basically - what I basically said to her was, you know, look, like, you don't know me. Here's who I am. Here's what I've done. You know, here's my background, and I'd like to be your showrunner. Here's what I love about your script. And I just talked about how what - what was relatable. To me in the script, what's - why it was important, why it's relevant. I talked about what I could bring to it. I thought - I talked about that. And either way, even if she didn't go with me or not, I was just happy to help her in any way possible.


PENNY: And I wrote her that letter and then...

SANDERS: She wasn't weirded out.

PENNY: She wasn't weirded out. She was like, let's meet. And so she was like, I have a book-signing at Eso Won Books in Leimert Park. So she and I talked for, like, 15 minutes afterwards.

SANDERS: Yeah. And she was cool and you were cool.

PENNY: And she was cool and I was cool. And we - you know, we realized, hey, we grew - we both grew up in - in Windsor Hills, in View Park.


PENNY: In LA. And really, now we both live in Inglewood, a block over from each other...


PENNY: ...So that's weird. We live in I-Wood. And then - but, yeah, we just - we just hit it off. And then after about 15 minutes, she was like, yeah, let's do this.

SANDERS: Wow. So right there on the spot, at her book signing, she's like, you got the job?

PENNY: And then - I mean, obviously I still had to be cleared through HBO and 3 Arts, the production company, and her managers. But on her side, I was, like, good. And so that's really how it happened. And...

SANDERS: That's so cool. That takes some bravery. I mean, I feel like I've never in my life written a letter to somebody being, like, hash tag, you need me.

PENNY: (Laughter).

SANDERS: Were you scared to do that?

PENNY: I mean, it's so funny. Like, the only other time I've written a letter, weirdly, was I wrote Larry Wilmore a letter. Like, he was speaking - this was, like, so many - I mean, I think I was in college or maybe just graduated from college and I heard him speak at, like, the writer's (unintelligible). And I wrote him this letter basically like, hey, I'll intern for you or, you know, whatever. You know, I just - I'm a young writer, blah blah blah (ph). And, you know, of course I never heard from him 'cause, like, you get a bunch of letters. You know, it's like, who's this guy? I don't know this guy from anybody else. But that was only other time, weirdly, I had written a letter.

And so at this point I was just like - and it was also a lesson, too, in, like, when you want something - right? - like, it reminds me of when I was watching "The Defiant Ones" and Jimmy Iovine was talking about, like, when you're trying to be or do something that you think is great. And like, it's not about your ego at that point. It's not about, like, anything else except being, like, if you want to be a part of it, figure out how to be a part of it and help make it great, help make it better.

And so, you know, if I wanted to I guess I could have been on, like, some ego. Like, I've written all this stuff, da-da-da-da-da (ph). Like - but that never even entered my mind to even approach it like that or think like that. I was just like, yo (ph), this is dope.


PENNY: I think I want to be a part of something that's dope. I never get to work with people of color.


PENNY: You know, you just have to, you know, just say, hey, how can I fit in there as opposed to thinking about your ego and all that other type of stuff.

SANDERS: So now you're showrunning. And you're doing so at a time when showrunning is kind of like a big deal. I feel like five years ago no one was talking about showrunners or you didn't know what showrunners did.

PENNY: Right. Right.

SANDERS: Now you guys are part of the celebrity of these shows. One, why is that the case? And two, what exactly does a showrunner do?

PENNY: That's a - those are good questions. I think in terms of why it's the case, I think - I think television taking on an air of freshness that movies used to have - like, when you think about movies now it's like...

SANDERS: The same Marvel remake.

PENNY: It's like a lot of - it's a lot of tent-pole - right? - 'cause that's what they're trying to make a lot of their big money on, right? So it's the next "Iron Man," the next whatever the things are - "Batman," whatever. Or you have these really small movies like "La-La Land" or "Moonlight" that are kind of like these little things that kind of are being made very small. Like, the middle-of-the-road, like, movies like when in the '80s when I was growing up, like the "Vacations" or the John Hughes types of teen movies or - they don't really kind of make those movies that much anymore because it's a weird price point to make them in. And they have to make a certain amount - you know what I mean?

SANDERS: Yeah. Yeah.

PENNY: Like, it's just a weird thing. They're banking on spending no money...

SANDERS: Or spending a lot of money.

PENNY: ...Or spending a lot of money.


PENNY: But this mid-level, like, 40 to $50 million movie is just like...

SANDERS: They don't do it.

PENNY: They just don't it anymore. So...

SANDERS: Whereas with, like, TV and streaming especially - it feels like with the advent of streaming there's just more space for creativity. You can have a season be 8, 10, 13 episodes, all that.

PENNY: Absolutely. And I think streaming made it like, one, you can take more chances, right?

SANDERS: Exactly.

PENNY: So it's edgy. You have other voices coming to...

SANDERS: And they're cinematic.

PENNY: Yes, it's very cinematic, right? And now there's not this taboo of like, oh, if you're a movie star and you do TV you're, like, taking a step back. Now it's cool.

SANDERS: Yeah. Now it's like Nicole Kidman getting Emmys for being on TV.

PENNY: Yeah, you've got Nicole Kidman. "True Detective," you've got Matthew McConaughey, Woody Harrelson. I mean, you just have a ton of people who are, like, wanting to do TV. And so I think in the wake of that people go, well, who created that?

SANDERS: Yeah. Yeah.

PENNY: Who created that? So that's cool. So in the way that people know directors for movies - right? - people now know writers for creating worlds, right? "Game Of Thrones," you know, again, "Stranger Things," whatever those shows are. And then also, in the advent of tweeting and tweeting as shows are happening, and you can talk to the show's creators. And like, all of that has put the creators, I think, specifically also in television front and center in a way that, like, movie directors aren't, in a way that movies, I think, also still feels inaccessible to people. Like, I don't know if Martin Scorsese's on Twitter, but I would probably guess he's not.

SANDERS: (Laughter) I would say no.

PENNY: And if he is, he's not tweeting with you. You know what I mean? So like...

SANDERS: Yeah, whereas you're there with...

PENNY: Right.

SANDERS: ...People watching your show.


SANDERS: All right. So tell me exactly - because I feel like the more I read about showrunners, the more I'm like, oh, my God, they do everything. Are they in charge of craft services, too? Like, what else do you do?

PENNY: (Laughter) So basically, the showrunner's job - so, like, in terms with Issa and I, like, we do things like really, like, 50-50 on everything from us figuring out sort of what the season's going to look like, kind of coming up with themes and ideas, to hiring all of our writers, to sitting with the writers and sort of shaping out and sort of molding the clay on the arcs of the season. Breaking all the stories with the writers. Supervising all the writing. Supervising all the rewrites. Casting every single actor on the show. Hiring every single director. Hiring our producers who are going to handle our crew. Hiring our directors of photography who are going to shoot the film. Dealing with the network and addressing notes. Figuring out how we're going to address rewrites.

SANDERS: It's too much.

PENNY: Being on set. Being there with the editors. Cutting the film. Cutting the show. Putting together music.

SANDERS: That's a lot.

PENNY: Yes. You know, talking to marketing once it's done. I mean, literally from the moment the first thought of a season is conceived...

SANDERS: You're in it.

PENNY: ...To when you finally see the end of the season, that's what the showrunner's responsible for.

SANDERS: How long - so how long is your average day?

PENNY: You know, we don't actually have bad days. I'm not a believer in long days. So we usually start a day...

SANDERS: (Snapping) Snaps to you, sir.

PENNY: ...Around 10.


PENNY: We're usually done, like, 5:30, 6. Like...


PENNY: ...I just - yeah. Like, you can stay and work until 10 and 11. I hear about those shows. And I've been on those shows. And it's like at a certain point what you're doing at 11 o'clock - because people just check out.


PENNY: And sometimes you're just - then you feel like you came up with the fix at, like, 2 o'clock in the morning. But really you're just like - everybody's on this, like, second wind, and, like, you don't know if it's going to be any good. You get back there the next day and you go, what the hell is this? This is crazy. And you've got to start over anyway.

SANDERS: Exactly.

PENNY: And so the other thing is, like, our show is about people who - our show specifically is about people who are dating and who are living life. And so it doesn't behoove us to have - and a lot of the writers go out and have stories...

SANDERS: From their dates.

PENNY: ...And they bring those stories back. And they live their life, right?


PENNY: And they bring those stories back, right? But if you're in the writers' room all day, it's very easy - I've seen very - I've seen bad examples where writers' rooms can kind of become echo chambers of other writers' stories. And you're more so talking about what you think is happening in life versus, like, what actually is happening.

SANDERS: They need lives.

PENNY: They need lives. And so...

SANDERS: Yeah. I get it.

PENNY: ...That's just a very important part of the show.

SANDERS: OK. So, like, you're working on the show "Insecure." You were on "Girlfriends." How did you get so good about putting yourself in the head space of strong black women?


PENNY: I was - I mean, I was raised by some strong black women.

SANDERS: There's that (laughter).

PENNY: My mom, my grandmother - I mean, my grandmothers. You know, I'm around one every day with my wife. But yeah, like, you know, I don't know. I feel like, you know, it's weird. Like, there - obviously there's some parts of being a woman I'll never be able to tap into just because I'm not a woman.


PENNY: But, I mean, I think there's a human part - I mean, my friends always say I'm a Drake type dude. I'd be in my feelings a lot. So maybe that's why I can write it good.

SANDERS: You don't like Drake, do you?

PENNY: Yeah, I like - what's wrong with Drake?

SANDERS: He a little too emo for me.

PENNY: Why - everybody want to hate on Drake. But let a Drake song - let "Started From The Bottom" drop right now and we would both be in the studio...

SANDERS: I mean, I would...

PENNY: Of course you would.

SANDERS: He makes bops.

PENNY: Hey, "Back To Back" drops right now, it's banging. I mean, I'll say - we can all - we can say what we want, but it's what it is, right?

SANDERS: I'll tell you one thing. The only good Drake albums are his mix tapes.

PENNY: No. "Take Care" is a good album and...

SANDERS: "Take Care's" fine.

PENNY: And the one started - the "Started From The Bottom" album is gold.

SANDERS: "So Far Gone" is good.

PENNY: "Worst Behavior"? "Worst Behavior's" not good? "PoundCake"? Stop it. Don't let me start playing this album.

SANDERS: (Laughter) I'll keep my...

PENNY: You can just cut this short - you can just cut this short and make the podcast about Drake. Don't - everybody want to hate, but everybody bumps Drake.

SANDERS: Well, every now and then I'll bump some Drake.

PENNY: I went to a Drake concert. Drake's concerts are insane. Nobody beats...

SANDERS: Not better than the Kanye concerts.

PENNY: Huh (ph)?

SANDERS: Not better than Kanye concerts.

PENNY: I mean, I haven't been to a Kanye...

SANDERS: You haven't been to a Kanye show?

PENNY: No, I ain't been to a Kanye.

SANDERS: I went to his tour just after "Graduation" dropped, and it was like I literally recommitted my life to Christ on the floor of that stadium.

PENNY: (Laughter) No, I hear it's religious.


PENNY: I hear it's mad spiritual.

SANDERS: Yes. Yes. Yes.

PENNY: I just can't - I don't know if I could be on the long - like, the 45-minute rants about commercialism.

SANDERS: I was seeing him before he was doing that, before he went off that deep end. Anyway, how did we get here? Kanye. Drake. They're both the...

PENNY: Oh, we were talking about black - we were talking about how I could write black women.


PENNY: But...

SANDERS: And Drake thinks he can, too, but he can't.

PENNY: Hey, don't tell Issa Rae that. You'll catch some hands.

SANDERS: I know. What was that line she had in "Insecure"? She was like, I just feel like he gets me.

PENNY: That's right, he gets her. Yeah, we had a Drake - we had a Drake go-out (ph) lyric all of season one. Last season was Frank Ocean. We'll figure out who we'll do this year. But, yeah, I mean, I think like, just - I think the one thing that - I'm not sure. Except I say that, like, the things that I like to write are about being emotionally truthful.


PENNY: So I think women are more truthful about a lot of things than men can be. So...

SANDERS: I'll snap to that.

PENNY: (Laughter) So I think maybe that's why. But, yeah, I don't know. I don't know.


PENNY: I just tapped into it.

SANDERS: Yeah, it worked.

All right, time for quick break. When we come back, we'll talk about how "Insecure" is part of this larger moment in the culture right now. I'll also put some questions to Prentice from Twitter. BRB.


SANDERS: So, like, you are heading this show that feels like it occupies a very unique space in the landscape of prestige television right now. Like, it symbolizes so much. Like, how do you think "Insecure" fits into the current state of TV right now?

PENNY: Yeah. I mean, I definitely think, like, you know, obviously we - you can't predict, like, who's going to become president and all that type of thing. But I do think the time we're in in terms of - look, we're in, like - you know, I mean, we're in a crazy time, right? So, like, "Insecure" - obviously, we have a lot of things that deal with race, right?


PENNY: And sociocultural issues. And so I think in the world we're talking about, where race is constantly, at some point in the day, being discussed, whether it's by the administration, whether it's by our citizens, whether it's internationally, race right now in this country is unavoidable. And I think, you know, we try to either, A, address that, B, poke fun at it, C, make you look at it from a different perspective than maybe you thought.

And I think also, too, like, I think right now, we're at a thing where, like, people want to categorize or demonize people of color - right? - whether it's black men with the police department. And people be like, I'm so afraid. I just saw a thing the other day where this security guard shot himself accidentally and blamed it on a black man who shot him.

SANDERS: I saw that.

PENNY: It's wild, right?

SANDERS: It's just like - yeah.

PENNY: Like, we're human beings. And I think "Insecure" does something where we show black people specifically...

SANDERS: Being human.

PENNY: ...Being human and being flawed and being imperfect and loving...


PENNY: ...And being - and just being fully dimensionalized as human beings.

SANDERS: Exactly.

PENNY: And I think that's where our show hits a spot right now in the cultural landscape. You know, it was so funny. I had a friend of mine who - a writer I worked with on another show. And he - a white guy. And he tweeted at me - he DM'ed and said, hey, man, I just started watching "Insecure." And he said, I just have to say, like, the show is amazing. And I asked - I said, hey, can I ever share your tweet? And he goes, yeah. So he goes, I'm playing catch-up - I'm reading the DM. It's so good. It's also making me think a lot - and he's a white guy...


PENNY: ...A lot about perspective and race and how you guys are showing me stuff I didn't know I knew about, even though I considered myself woke. I now understand your experience of being the only person of color in a writer's room full of white guys. And then I go, well, what made you say that? I said thank you, obviously, for saying that.


PENNY: It's a weird thing. And he goes - I said, well, what has it made you think? And he responds. He says, it's made me think about how to approach representation in my own writing. He said, there's a fine line, it seems, between writing diverse characters and cultural appropriation. And I was just like, can I share that?


PENNY: And I said that's such a - like, I think our show is, like, highlighting that, right?


PENNY: That, like, we're letting you in on a window that black people experience that you may on its surface - you may think, oh, I know about this. And then - but we're kind of letting you in on a window of like, oh, no, maybe - do I do that...

SANDERS: Exactly.

PENNY: ...You know? And it's not from, like, an accusatory standpoint - just from like a, wow, I didn't know that's what it looks like from your guys' perspective.

SANDERS: I didn't know, exactly, yeah.

PENNY: Yeah.

SANDERS: Well - and I also love the way that you deal with race on the show. You admit that black characters, like Molly and Issa, can also sometimes get it wrong on race.

PENNY: Oh, for sure.

SANDERS: Like, there's this plotline where Issa - with the principal of the school that she works in, they're kind of doing bad by brown students, you know? And it's like - honestly, it's refreshing to see that and have you guys say, black folks don't know it all, either. Like...


SANDERS: ...When she's meeting the guy for the date who's a Latino.

PENNY: (Laughter) Right.

SANDERS: I'm just like, girl, what are you doing?

PENNY: (Laughter).

SANDERS: And, like, even when her and Molly have that dinner - this Arabic dinner - and, like, they're dressing up like they're Arabic. I was like, this feels weird.

PENNY: (Laughter).

SANDERS: But you guys went there. And I'm just like - it was refreshing to see that even people that look like me that some people expect to be perma-woke all the time...

PENNY: No, not at all.

SANDERS: ...Can get it wrong.

PENNY: Can totally get it wrong. And I think it speaks to just a human thing, which is, like, you're sympathetic to the perspective in which you see things, right? And if you don't see it from that perspective, then you, like - or you don't have that experience, you find it hard to tap into it. And I think - you know, we often criticize white people for not doing that. But I was like, we're just as guilty. Like we're saying, it's like we're fully dimensionalized.

SANDERS: Yes, yes.

PENNY: Like, we're not always - like, one of the things that really frustrates me sometimes is when I see - some movies or some things that present us...

SANDERS: As magical Negroes.

PENNY: ...As magical and very Martin Luther King...


PENNY: ...All the time. But we're not always like these people who can rise above a situation. You know what I mean?

PENNY: Exactly.

PENNY: It's like, we're flawed and imperfect...

SANDERS: He was flawed.

PENNY: ...And all these things too, yeah.

SANDERS: I mean, like, Dr. King had a few classes where he almost failed. He stepped out on his wife sometimes. Like, we should be able to say that.

PENNY: Yeah, he wasn't a perfect human being. Right, he was - but I think there is this thing that, like, everybody always has to be, you know, doing something for the movement. Or we're always these sort of, like - you always assume the black person you know - like, the one black guy you know can dance. Or you always assume that, like, your black friend - like, if you're white, you might think, like, your black friend has the best advice.

SANDERS: Yeah, you might assume that your black friend likes Drake.

PENNY: Right - whoa, whoa, whoa.


SANDERS: I'm kidding. I'm kidding. I'm going to let it go now. What's your favorite Drake song?

PENNY: Ooh, I mean, I love "Started From The Bottom" just because it's just like...


PENNY: But I also love - like, "Marvins Room" is so dope.


PENNY: I love "How 'Bout Now." "How 'Bout Now" is my joint when I'm on, like, some petty stuff.

SANDERS: (Laughter) I like - and this was from the first mixtape - the one with Lil' Wayne, "I'm Goin In."

PENNY: Oh, yeah, "I'm Going In." That's dope, too.

SANDERS: (Singing) I support a good song. Yeah.

PENNY: See, you coming around.

SANDERS: (Laughter) When did you know that you wanted to do this type of work - showbusiness, TV?

PENNY: I was always interested. I grew up an only child. And I grew up at a time when, like, I had, like - not grandparents - like, grandparents now are cool. They travel. Grandparents are on Facebook and Twitter. Like, I grew up with, like, '80s grandparents...

SANDERS: (Laughter).

PENNY: ...Who were like - who had a floor-model TV, who watched the news for four hours straight, didn't play outside with you. It was like, go play, and just come back before the streetlights come on. You know what I mean?

SANDERS: Yeah, yeah.

PENNY: And so I was the only child, so I had to entertain myself. And so I - you know, when I was done doing my homework or whatever, I would just watch a lot of TV. I didn't want to watch what they watched. So there was, like, a little black-and-white TV sometimes at my grandparents' house or - and wherever I'd watch, and I just...

SANDERS: So what'd you watch?

PENNY: I would watch, I mean, everything of that day, like "Diff'rent Strokes," "The Jeffersons," "Growing Pains," "Family Ties," "It's Your Move" with Jason Bateman. Shoutout to that show. People will sleep on that show. "Valerie's Family" - you know, all those - all family thing - you know, all the classic '80s shows - "Love Boat," "Fantasy Island," "Dukes of Hazzard."

SANDERS: You watched a lot of TV.

PENNY: Yeah, it was - I was - a lot of TV. So I would just write my own stories. I'd write my own versions of those stories or whatever.

SANDERS: ...Of the show that you watched.

PENNY: No, just of, like, whatever. But I understood like, oh, a character has to speak, so I'd do - I mean, I didn't know how it - what a script looked like. I was writing, like, it in, like, a - more like probably like how plays are written, and sometimes it was just, like, in that kind of a style, I guess.

SANDERS: So you were writing your own TV shows as a kid.

PENNY: Yeah, as a kid.

SANDERS: How old were you when you were doing this?

PENNY: Maybe, like, 8 or 9, maybe 10. And...

SANDERS: Wow. You were ahead of your time. I mean, when I was 8 or 9, I was not writing my own scripts.

PENNY: Well, I like to write. You know, like, my parents used to make me, like, cut out the newspaper and do, like, current events, like, once or twice a week.

SANDERS: Oh, wow.

PENNY: ...And, like, do the who, what, where, when, why and how of an article, you know? So, like, writing to me - and my mom's an attorney, so she was a writer. And, like, she writes a lot, obviously. And my grand - and two of my grandparents were teachers, so, like, writing and all that was very...

SANDERS: It was in the air.

PENNY: Yeah - in my house growing up a lot, like, some - like, seeing writing as a thing.

SANDERS: So your grandparents were in the house with your mom too.

PENNY: No. And but, like, when my mom - when my parents split, my mother decided to go to law school. And so when my mother was going to law school at night...

SANDERS: They would watch you, gotcha (ph).

PENNY: I would be at my grandparents', and so they would watch me certain evenings. And so, but yeah, but I was also really interested in marine biology. I loved the animals. I loved the water. It was a - it's a weird thing. And then I remember, when I got to high school, our school was kind of by the water, so we had, like, a marine biology, like, elective. And so I remember I took that, and I was like, this is really dope.

And then I remember I started to have to make a choice about where I was going to go to school because I was either looking - I was looking at USC and NYU, obviously, if I wanted to do writing. And then I was looking at, like, UC Irvine and other schools that were more geared towards a life of doing things in the ocean.


PENNY: And I remember I had to make a hard choice about where I was going to really apply. And I just was like, I think I love this thing more than, like, beluga whales.

SANDERS: (Laughter) It paid off.

PENNY: And so I went that way. Yeah, it was - it's a - I was, you know...

SANDERS: So you went to USC.

PENNY: Yeah, I went to USC. I went to film school at USC.

SANDERS: OK. What do you think your life would've looked like if you ended up a marine biologist?

PENNY: I mean, there's a part of it that I think is kind of cool though, right? Like, there'd be a part of it where I'm like, man, I probably would've travel the world at a much younger age, you know? But maybe if I were to work with James Cameron, and gone down the Titanic and do some cool stuff like that, maybe that would've been cool, you know what I mean? Who knows?

SANDERS: I want to see a collab project with Prentice Penny and James Cameron. Please do that.

PENNY: Man, you and me both. Man, you and my pocketbook both.

SANDERS: (Laughter) So I want to talk about the relationship between this show and Twitter. There were two moments in season two that had very interesting responses on Twitter. And there was one I felt like, y'all were prepared for it to spark conversation. But I think the other might've caught y'all off guard.

You know, there was that whole plotline with Issa and oral sex. And some things were said at - all throughout the episode, but I think you guys were ready to have people respond to it and talk about it. And that did happen online. But there was another part of the season where there was this discussion on black Twitter over whether or not you guys were showing enough condoms in the show. And it just felt like, where did that come from? Did that kind of catch you off guard?

PENNY: Yeah, I mean, I, honestly - because, one, it was never a discussion. One, it - yes. And I think - and I, also, too - you have to be - I always think you have to be careful in terms of, like, you know, Twitter could kind of become a Twitter tornado, right?

SANDERS: That's a good word for it.

PENNY: So it's, like - it kind of it becomes like a black hole. Like, it sucks a lot of energy. You could also fool yourself into thinking it's the thing everybody's talking about - you know? - because everybody that watches our show doesn't tweet, you know?

SANDERS: So true.

PENNY: And people who were just as much coming out, saying, there should be more condoms - were people coming out also saying, it's not a documentary. It's not a this. It's a comedy show. You shouldn't need a comedy show to tell you to use a condom in 2017.

SANDERS: Come on. (Snapping). Yeah.

PENNY: So, you know, like - so I think, like, creatively, you know, you have 27, 28 minutes to tell your show. So a lot of times, when we are seeing sex, like when Lawrence is having sex with Tasha in the first episode of season two, we're just cutting into the middle of it. So we're not - we don't have time to say, like, you know, oh...

SANDERS: Yeah, you don't have time for a PSA.

PENNY: Yeah, you're trying to create an emotional feeling. Not, hey - also, hey, guys, also use condoms. You know, so - and it's so...

SANDERS: Also get tested every six months. Like, I mean, what is this stuff?

PENNY: Also, like, be a grown-up. You know what I mean? Like - but I think beyond any of that is just, like - it's, like, we're not - we're always trying to imply that our characters are safe, or we'll put them in the background of scenes. And so, like, when Lawrence has a threesome, it's on the dresser. You know, when the girls go to the Sexplosion, there's a whole conversation about - they're actually picking up condoms and talking about condoms. And I was like, also, I don't know other shows that, like, get that heat. I was like, does anybody watch "Scandal" and go...

SANDERS: Oh, totally.

PENNY: Or does anybody watch, you know, "House Of Cards" and go, whoa, why isn't - why aren't the Underwoods using condoms when they having affairs, you know?


PENNY: It was just a weird - I was like, I don't know where this was coming from. And so I'm glad it kind of just, like - yeah.

SANDERS: ...Kind of went away. It's funny, yeah. I was reading some different interview you did. And you said, quote, "you have to be careful because if you try to go up against Twitter, especially black Twitter, you lose out the gate. It's too big of a force." That's something.

PENNY: It is. Black Twitter is no joke. But, you know, black Twitter is also the reason why our show's successful. You know what I mean? And obviously, we love all Twitter - white Twitter, Asian Twitter. Shoutout to Latino Twitter, all the Twitters.

SANDERS: Yeah, shoutout, shoutout.

PENNY: But, you know, but black Twitter...

SANDERS: ...Even Drake twitter. OK, I'm gonna (ph) stop (laughter).

PENNY: There, see? You're coming around. Drake off. But I think that's kind of like the point, you know, is like, their support. So you got to take - you know, I always feel like black Twitter's like your auntie when your auntie is like - you know, she giving you crap, but she's also like, OK, I see you. I see you with the graduation. You graduated. OK, I'm with you.

SANDERS: Exactly (laughter). Yeah.

PENNY: You know, or, you know, your hair looking shoddy, or girl, like, your slip's showing, you know? Black Twitter is going to do all of that. You got to love all of it.

SANDERS: You got to love it all.

PENNY: So I rather have - and honestly, I would rather have Twitter care that they want to see black people being responsible than not.

SANDERS: I hear you.

PENNY: So for that, I'm glad that they care about our show and care about the issue enough that they think about it. So I'm glad for that perspective.

SANDERS: It's true. And I also think part of why black Twitter is watching "Insecure" with such focus is because it feels like it's something new. And it feels like it's something new for black America that we have not seen before. So I think a lot of folks, it comes out of a place of wanting to see this thing be the best it can be.

PENNY: For sure.

SANDERS: And that can feel a bit paternalistic, and like, where the hell are you coming from, black Twitter? But most of it feels like it's a out of place of, like, actual, genuine love for that show.

PENNY: Yeah, and I think it's the same thing where, like, when you feel like this doesn't get a chance to happen every day...

SANDERS: Mmm hmm, so it better be good.

PENNY: ...So you kind of wanting us to be all things to all people, and it's like, obviously...

SANDERS: ...Which is impossible.

PENNY: ...Which is impossible. You know, I'm hopeful that, like, it - our show doesn't have to be the anomaly. And so that's why it's good to see shows like - obviously, like "Atlanta," you know, Nicole Byer, you know, and to see other voices of color like 2 Dope Queens, and Pheebs and all those people just, like, get their time, you know? And...

SANDERS: Yeah, yeah.

PENNY: For sure.

SANDERS: What should we expect in season three of "Insecure"?

PENNY: In terms of any info, I would say...

SANDERS: (Laughter) None.

PENNY: I'm not going to say anything. But, I mean, honestly, Issa and I are supposed to meet next week to start talking about season three. So she and I usually get together for about a day, and we just sort of start talking out ideas and themes. So she and I are going to start talking of that. But I think in terms of thematically, I think you can expect what our show does well, which is characters making some good decisions, characters making some not-great decisions. So, yeah, I don't know. I'm - I've tried to, like, block the show out of my mind for a little bit so I can kind of come back to it fresh.

SANDERS: I hear you. I got one last favor to ask you.


SANDERS: I tweeted this morning that I was going to be interviewing you. And I asked Twitter if they had questions for you.

PENNY: Oh, snap.

SANDERS: I will read a few to you. Brionna Jimerson wrote, I'd like to know a bit more about the show's developing use of LA as a character in the series. Last episode of season two was spot on, #IWood.

PENNY: (Laughter).

SANDERS: I did like the IWood (ph) plotline.

PENNY: Yeah, I mean I live in Inglewood right now. The - all the things that are in our show are actually happening in Inglewood, obviously, because they're building the new football stadium. But yeah, I mean, I think, you know, Issa and I are both, like, native Angelenos from a very specific area. And I think in the way that, like, Issa has said that, like, in the way that Woody Allen does New York, she wants to do for LA. And I couldn't agree more because I think, like, you know, people think of LA, they think of "The Entourage" LA which is, like, Malibu, Beverly Hills. Or you think of the other way, which is like, you go Compton, and - you know, all the crazy stuff. And I'm like, there's a ton of LA that exist in between those, you know, bookends.

SANDERS: Totally.

PENNY: ...That is beautiful and amazing. And I think we will, like, just keep - like, continue to explore these areas that don't really get a lot of looks.

SANDERS: Yeah. Last one - Toni wanted to know the makeup of the writers room - age, gender, race. And you've talked about before wanting to make sure that your writers' rooms have a lot of different perspectives in them.

PENNY: Yeah, I mean, our - if I can try to think real - as quickly as I can, we have three white writers, one Latino writer, seven African-American writers, four men, eight women, one, two, three, four gay, lesbian writers, three drama writers, nine comedy writers.

SANDERS: You know your people.

PENNY: Yeah, I had to think quickly as I go around the writers' room. I'm seeing it in my head.

SANDERS: Yeah, yeah. Hey, man. Well, I wish you all the best. I was thinking to myself today, I was like, oh, this is Prentice Penny's year of Penny.

PENNY: (Laughter) Shoutout.

SANDERS: "Happy Endings" reference.

PENNY: "Happy Endings" shoutout. I love that. That's what's up.

SANDERS: Yeah, man. Keep it up.

PENNY: I appreciate that. Go play some Drake.

SANDERS: (Laughter).


DRAKE: (Rapping) ...My whole team here. Started from the bottom, now we [expletive] here.

SANDERS: All right, man - appreciate it.

PENNY: Absolutely. Take care.

SANDERS: All right. Bye.


SANDERS: Prentice Penny - it's such a great name - had a lot of fun talking to him. Go check out the first two seasons of "Insecure" on HBO NOW. Also, if you want to be my best friend forever, watch the show Prentice used to write on, "Happy Endings." It's so delightful. We'll be back on Friday with a wrap on the week of news and culture and everything. Also, send us an audio message sharing the best thing that's happened to you all week. Send it to Sam Sanders at npr.org. Thank you for listening. I'm Sam Sanders - talk soon.


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