Issa Rae’s Insecure Rewind Podcast ‘Block Party’ + Building Your Foundation & Remembering Your Why

Summary

The Latest with Loren LoRosa

Issa Rae’s Insecure Rewind Podcast ‘Block Party’ + Building Your Foundation & Remembering Your Why

Date: May 18, 2026
Host: Lauren LaRosa (The Black Effect Podcast Network & iHeartPodcasts)

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Episode Overview

In this episode, Lauren LaRosa explores the importance of building a strong personal and professional foundation and remembering your "why"—the purpose behind your grind. She links those themes to the recent launch of Block Party, Issa Rae’s “Insecure Rewind” podcast. Lauren dives into Issa’s journey, the cultural significance of Insecure, exclusive revelations about the show’s development, and the pressures and possibilities faced by contemporary Black creatives.

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Key Discussion Points & Insights

1. Monday Motivations & the Power of Foundation

• Lauren opens up about her own weekly reset ritual, viewing Mondays as a symbol of new beginnings and fresh opportunity.
• She stresses:
  • The value of discipline, honesty, accountability, and execution in building a real foundation in any life endeavor.
  • The importance of stepping back to re-evaluate overarching goals and not becoming consumed by day-to-day tasks.
• Quote:
  • "Things can’t just be one thing onto the next. You’ll never build a real foundation that way… what is your house built on that is going to keep the structure of your home there and appreciating and growth and value?" (05:32)
• She especially acknowledges the extra challenges faced by first-generation success stories—those breaking barriers their families haven’t previously crossed.

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2. Reflecting on Your “Why”

• Lauren discusses the need to continually revisit the reason behind your ambitions, especially after achieving initial milestones.
• She admits the ongoing difficulties of sustaining new success:
  • "There’s a lot to figure out… You gotta sustain it, you gotta make this make sense so that next generation coming behind you ain’t gotta A, B, C, and D." (10:37)
• Listener Engagement:
  • She encourages listeners to reflect alongside her:
    • "Hopefully, because I’m reflecting, y’all are reflecting with me and really taking the time every day when you listen … to really check in on yourself as well, too." (12:27)

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3. Spotlight: Issa Rae’s 'Block Party' — Insecure Rewind Podcast

A. Overview & Impact

• Lauren recaps the concept of Block Party, a rewatch podcast where Issa Rae and Prentice Penny revisit Insecure’s pivotal TV moments as well as behind-the-scenes stories.
  • "Issa’s effect … is still so fresh. People are still following that model or attempting to… Black creatives and storytellers, and even just the coloring of Black content… Insecure changed a lot of that." (17:56–19:02)
• She highlights Insecure's legacy in representation:
  • Two brown-skinned Black women as leads on a major network; shifting TV aesthetics for Black stories.
• Insecure’s success is celebrated through numerous Emmy, Golden Globe, and NAACP Image Award nominations.

B. Memorable Quote / Anecdote

• Lauren recalls attending a Revolt conference as an aspiring creative and seeing Issa Rae speak about her early YouTube days:
  • "Unless you were really closely watching Issa or you tried to do it yourself, you don’t understand how hard it is to do what she did — and do it well…" (24:53–26:05)

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4. Behind-the-Scenes: The Chris Rock Story

• Issa Rae reveals HBO initially wanted Chris Rock to direct Insecure, which she opposed because the story was so deeply rooted in Los Angeles.
  • Issa Rae (Clip):
    • "HBO really wanted Chris Rock to direct… He wanted to fake New York for LA. I was like, but I want to show off LA." (25:39–26:35)
  • Chris Rock eventually stepped away and later admitted to Issa:
    • "I would have fucked your shit up." (28:17–28:20)
• The segment highlights the pressures Black creatives face in standing their ground:
  • Kim Coles:
    • "Sometimes when you, like... have to accept what they tell you, even if you know in your gut isn’t right." (28:26–29:00)
  • Lauren:
    • "As a Black creative in this space… you feel like, if I don’t do this this way, the opportunity will be gone. That is such an anxiety point." (29:16–30:17)

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5. Intentional Casting Choices in 'Insecure'

• Issa Rae on breaking colorism tropes in casting:
  • Issa Rae:
    • "These are two dark-skinned leads because this is true to life. I was very specific about that… I wanted to have, like, real people. Definitely not celebrities." (36:06–37:34)

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6. Building in Public & Passing the Torch

• Lauren discusses the evolution of the digital creative landscape, emphasizing how icons now build their brands in public, under constant scrutiny.
  • Cites a viral commentary by JPW Photo:
    • "The next generation of icons is already here… we’re literally watching those icons get built in real time." (38:28–39:34)
• Lauren reflects on Issa Rae’s longstanding commitment to platforming up-and-coming creators and how these choices build a legacy.
  • "It takes very strong people to be able to do that on a high level… learning in front of the world, as the world is critiquing you very, very loudly, which also can affect, either in a negative or positive way, your dollar." (39:34–41:03)

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Notable Quotes & Memorable Moments

• Lauren on foundation:
  • "Foundation is important. And foundation comes with a lot of discipline, a lot of honesty and accountability, execution. But it also comes with understanding that direction is important." (06:17)
• Issa Rae on Chris Rock departing:
  • "He was like, I would have fucked your shit up." (28:17)
• Lauren on Black creatives’ pressure:
  • "There’s such a pressure point… When you’re succeeding at a certain level, there’s a pressure to top yourself, but also to keep it going because things change around that success." (30:22)
• Issa Rae on Molly & representation:
  • "I don’t want to do the, oh, dark skin, light skin combination that’s always in these black shows. These are two dark skinned leads because this is true to life." (36:14)

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Essential Timestamps

| Timestamp | Segment/Theme | |-----------|---------------------------------------------------------------------------------------------------| | 05:32 | Lauren’s reflection on foundation and goal-setting | | 10:37 | Sustaining success and building for the next generation | | 12:27 | Encouragement for listeners to self-reflect | | 17:56 | Lauren on Insecure’s legacy and the Block Party podcast | | 25:39 | Issa Rae recounts HBO's push for Chris Rock and her resistance | | 28:17 | Chris Rock’s iconic comment ("I would have fucked your shit up") | | 29:00 | Kim Coles and Lauren on creative pressure and navigating opportunity as Black artists | | 36:06 | Issa on deliberate casting and colorism | | 38:28 | JPW Photo commentary on generational icons and building legacy live | | 39:34 | Lauren praises Issa’s ongoing platforming and transparency | | 41:03 | Wrapping up with reflections on challenge, legacy, and optimism |

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Overall Tone & Takeaways

• Intimate, conversational, and highly motivational—Lauren brings listeners into her evolving thought process.
• Lauren is candid about creative struggles and driven by admiration for Issa Rae’s journey and impact.
• The conversation blends actionable wisdom (foundation, remembering your “why”) with an inspiring celebration of modern Black artistic trailblazers.

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How to Listen & Further Resources

• Block Party (the Insecure Rewind podcast) is available on Hooray Media’s YouTube Channel.
• Lauren LaRosa invites audience interaction:
  • "If anybody else is going through this in real time in their life, I want to hear from y’all @LaurenLaRosa everywhere." (11:48)
• The episode is rich with references, encouragement, and a reminder that success in the public eye is both fraught and deeply rewarding.

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Transcript

[Lauren LaRosa]

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[Lauren LaRosa]

I'm the home girl that knows a little bit about everything

[Issa Rae]

and everybody, you know, she don't lie about that, right?

[Lauren LaRosa]

Lauren came in hot.

[Wheezy (Wheezy WTF Host)]

Hey, y'.

[Lauren LaRosa]

All. What's up? Up? It's Lauren LaRosa, and this is another episode of the Latest with Lauren LaRosa. This is your daily dig on all things pop culture, entertainment news, and all of the conversations that shake the room. Baby. Now, we all know my lowriders. We always start off with a behind the scenes of the grind. Check in, back on the grinding, and it is the start of the week. It is Monday. And, you know, I think, you know, Monday, for me, it always symbolizes the chance to, like, start fresh. Like, no matter what it is that you do, no matter what your profession is, you know, what your focus is daily. Monday is like, a new sense of, like, optimism. I feel like Sundays are, like, the preparation for that. It's like, okay, you know, Friday, you're still dealing with whatever was thrown your way that week. You know, good, bad, or indifferent. Saturday, put it behind you. You might be out, grab a drink. You're not really locked in to all of the things. You're kind of like, numb on a Saturday. Sunday is the day where you really tap in. Okay? My week is about to start. I want to clean out this place so I can bring in what this new week is going to usher. And then Monday, baby, the ushers come out with the white gloves, the flat shoes in the church, and the hats, okay? And usher in all the new things, all the new blessings and new lessons of a new week. And for me, I'm always excited about new and what new is to come in life in a week, in a month, in a day, in an opportunity. But I do think that there are things that, you know as you're going into deeper, deeper into these new weeks, these new months, you know, deeper and deeper into whatever goals you have set for yourself this year. And, y' all know the year is flying by. Like, summertime is here. I think that, like, foundation is important. I talked to you guys on my last episode and shout out to some of the lowriders on X and threads. I saw you guys discussing a bit about what we talked in the behind the scenes of the grind. Check in on X. One person tweeted me, so Angel Lee writing tweeted me, shout out to Angel Lee writing one of our low riders on X. And she says, I love seeing creatives grow in real time at Lauren LaRosa. Thanks for the transparency. And we talked a lot in that last. In our last episode. If you did not take a listen to the episode prior to this one, before pressing that play button, make sure you go and press the play button on that prior episode, after this one or before and come on right back over. Up to you. But we talked a lot about just, you know, building and trying to figure that out, man, how real that gets and what I'm experiencing in real time. And you know, and I think my biggest, you know, thing I'm learning a lot of while doing all of that, it's like no matter, you know, the new team that you build, the new opportunities you walk into, the new rooms you walk into, whether they're going good or not. Foundation is important. And foundation comes with a lot of discipline, a lot of discipline. And foundation also comes with a lot of honesty and accountability, execution. But it also comes with like, understanding that, you know, direction is important. And I think sometimes, you know, when you're creative, when you're a dreamer, when you're a person getting up every day to accomplish anything, even if it's just getting your kids to school on time, I think sometimes, like, we forget to think about like, what the overall, you know, big picture of the stuff is. Like, we're just focused on that one thing. Like, all right, I got to get the kids to school on time. I gotta make it to work on time. I got this presentation at work and I'm just trying to get through it and impress my boss. I, you know, me, I'm preparing for my segments the night before I get to work the next day. Yo, I just want to nail these segments. I want the room to love what we talking about, love the conversation, and then boom, onto the next day. But as I began to just navigate different things in my personal life and career, I think a lot of what I'm learning is like, things can't just be like one thing onto the next. You'll never build a real foundation that way. And when I say foundation, I don't mean like a non profit organization or a business or anything. I mean like an actual foundation. Like, you think about a house, like, what is your house built on that is going to keep the structure of your home there and appreciating and growth and value and, you know, best protecting all the people that you bring into your house. And I made the example of like, you know, us just preparing for something, getting it done whether we do well at it or not. But normally if you do well at it, it's easier for you to just be like, did that. All right, bet, period. Move On. I brought that up because one of the things that I had a very heavy thought about today, and I was like, I know that this is God, and everything that I'm doing, I gotta go back to, like, always remembering, like, what. Like, what is the end goal? Like, we are here now and we are doing things, but what is that end goal? And there was a time where, you know, and this happens with anybody doing anything, like, when you first get into something or start doing something or even like a new relationship, everything is so, like, you know, you're wide open and, you know, googly eyes and all the things. So you're not really thinking too much about what you were thinking about before you had that new thing. Like, you know, all of the. Yo, if I just get this shot, here's what I really, you know, want to stand for. Here's the message I really want to put out into the world. Here is the. The lane of growth. I really want to see for myself. Here's the legacy I want to leave or in a relationship. Here's the way I next time. Here's how I'm going to love a person. And then you get the person or you get the opportunity and you in it and you feeling like that for a while and then things switch, things happen. But it's always about remembering what that original why was and that once you have those conversations with yourself, I think, you know, the foundation building isn't easy. I'm not going to lie to y'. All. This stuff is not easy whatsoever. Especially shout out to all my first generation people out there. And I'm not an immigrant. I don't mean first generation to the country, but y' all too. I'm just not in that, you know, pull the people. When I say that, people always think I'm saying that, like, I'm a first generation citizen. I'm not. When I say first generation, I mean first generation, like, of success level, first generation college grad. Like, there's a lot of things that I'm doing that, you know, my immediate family has never witnessed. So I'm figuring things out in real time. And before I had a lot of these things to figure out, I knew, like, all right, when I get this shot, here's how I'm going to run this up. Here's how I'm going to do this. And now when you get in it, you accomplish a lot of those goals. And it's like, oh, but wait, you gotta sustain it. You gotta make this make sense so that, you know, next generation coming behind you ain't gotta A, B, C, and D. So there's a lot to figure out. And as I'm having these conversations, trying to build team and, you know, and all these things, that stuff is so important to me because I want people aligned with what that goal is for myself, you know, and that's what I'm saying. Like, it's so important to be able to kind of, like, take a step back and out of everything when you get a chance to schedule that time. Like, I scheduled time for myself this weekend and even next weekend to know that, like, okay, I ain't gonna be doing much of nothing. Like, even if I go, you know, to Delaware, be with my family, even that, in a sense, helps me always remember, like, you know, before things were moving so fast where you kind of couldn't take a second to sit and think, what were you thinking of? What was the goal? What were you saying you needed to be disciplined in? And why? Like, get back to the essence of the why, and then understanding that will help you bring in the right people, you know, at least on face value. Hiring firing is a thing. But, yeah, like, man, everything is growing pains, and I am actively going through it, but this isn't a woe is me conversation about that at all. Like, I'm actually, like, excited to be going through this. I feel like it signals growth. It signals, like I said, that started a week. How that fresh feeling is it. It. It signals that for me, like, okay, new levels mean, you know, new people coming in mean new levels, new opportunity, new things that we'll get to do together. So I'm excited. If anybody else is going through this in real time in their life, I want to hear from y' all at Lauren LaRosa. L O R E N L O R O S A everywhere. Y' all know, the behind the scenes of the grind. Check in for me is a chance to really sit down and just kind of put all the thoughts together that I've had circulating in my head for the last, like, 24 hours, but also to really just check in on myself, because I know I don't take the time to do it. So I do it here with y', all, hopefully, because I'm reflecting, y' all are reflecting with me and really taking the time every day when you listen to the Latest with Lauren LaRosa to really check in on yourself as well, too. Now let's get on into the latest. Man, I watched a podcast that really just made me talking about, like, figuring things out for the first time and Your why and your purpose and just all of those things for real. But also being an artist and also having something to say. I watched the Insecure Rewind podcast, Issa Rae. That Issa Rae just dropped and she dropped this podcast with Princess Penny who was, you know, her right hand man. And everything they did with Insecure, the show on hbcu. Wow. On hbo. And I was sitting there for that hour like, I need this podcast so bad.

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[Lauren LaRosa]

Connecting changes everything.

[Wheezy (Wheezy WTF Host)]

AT&T this is wheezy. WTF from decisions, decisions. You know, a lot of us grew up not fully trusting the healthcare system. And honestly, the system has given us plenty of reasons to feel that way. But now it's time for us to take control of the conversation, to take control of our sexual health. Learn the facts, ask questions, and advocate for ourselves. That's how we start changing the story. So let's talk. We like to think HIV is something that affects other people, but it is hitting our own community hard. Black women make up about 13% of women in the US but account for nearly half of all new HIV diagnoses around women. And being proactive doesn't mean you just don't trust your partner. It just means you trust yourself enough to stay in control. So know your options, ask questions, and protect your peace and your body. That's real power. Because protecting yourself isn't embarrassing, it's responsible. Sex is normal. Protecting yourself should be normal too. Actually, it's kind of Badass. Taking control of your sexual health is grown woman energy sponsored by Care for the Culture from Gilead Sciences.

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[Cal Penn]

hey everyone, it's Cal Penn. I'm the host of Irsay the Audible and I Heart Audiobook Club. This week on the podcast I am sitting down with Ray Porter, the narrator of Andy Weir's audiobook project, Hail Mary Massive sci fi adventure about survival and science and what happens when you wake up alone, very far from Earth.

[Ray Porter]

I really had to make a decision because I caught myself getting that frog in my throat and starting to get teary as I'm narrating some of these sections and it's like, okay, yo yo yo, is this indulgent? And I really thought about it. I was like, no. At this point it would kind of be betraying the trust the author and the listener have in telling this story if I don't go through it. But there's places in this book that that deeply, emotionally affected me and I left it on the mic. That's great because it served the story. People will say like, oh my God, I cried at the end. It's like, yeah dude, me too.

[Cal Penn]

Listen to Irsay the Audible and iHeart audiobook club on the iHeartradio app or wherever you get your podcasts.

[Lauren LaRosa]

So on its surface, this podcast and the podcast is called Block Party B L O C C Party and anybody that watched Ins understand why that name is so reminiscent of, you know, who we watch Issa D grow into on the show and all of her life journey as she was figuring out foundation and all the things. It's an Insecure rewatch podcast and they visit all of the moments from the show that were like big moments and talk through them, but they also like reveal behind the scenes stories and unpacked everything. Now 10 years later and even reading that it's been 10 years since Insecure dropped. Insecure dropped on October 9, 2016 on HBCU. Chad, I keep being about to see, say HBCU. Insecure dropped on October 9th, 2016 on HBO. It doesn't even feel like 10 years. I feel like Issa's effect of what she did with Insecure is still so fresh and people are still following that model or attempting to and creators are still feeling real bold and out here, like the black creatives and storytellers and even just like the coloring of black content. And when I say coloring, I mean like the actual coloring, like the colors that you see on the, like the screen when you're watching, watching it. I feel like Insecure changed a lot of that for how people were shooting black people, the angles, the like, it's just so much cinematically that it changed that I still see today. So it still feels so fresh. There was so much storyline wise that they changed that I still see today. Even just having two black girls, brown skinned black women as leads of a major network TV show. Like there's still not a lot of that. So Insecure still feels so freshly groundbreaking because it just, it meant so much at the time and it's just, I don't know, it's just still here. Like it, it doesn't feel like 10 years whatsoever. But yeah, so they sit down and they have these conversations. They dropped their first episode. The first episode was an hour long. And let me tell y' all something. I enjoyed every single minute of the hour. So we are going to get into it. I think people don't talk enough about. Well, I feel like I was gonna say people don't talk enough about the success of Insecure, but I just went on for like 20 minutes about the success of Insecure. I think people talk about the success of Insecure, but I don't know, I just want to talk some more about it. So when Insecure hit, I remember because I went to Diddy used to have these. Wow. Saying Diddy used to have and then leaving people on a cliffhanger about what adventure about to Mention is crazy in 2026, but did he used to have these Revolt conferences in Miami, and it was literally like a huge conference. He would bring all of the, like, biggest up and coming creators, creators that was, you know, already up. It would be like a range, but, like, you could walk around and literally just run into anybody. Like celebrities, the biggest producers in the music game, in the television game, EPS executives. Like, I. I remember going there and I just used to walk around with, like, resumes for people, for companies that I was. Because at the time, I was like, you know, being an actual talent in the industry, I was like, man, everybody's trying to do that. It's so hard to do. And I didn't really have a reel or anything like that. I'm like, if I could just use my degree to get in an entertainment company, I'll work my way on camera or wherever else. So I would go to the Revolt conference and just try and figure it out, like, any way I could. Like, yo, who has a marketing team? Who has a this? But I remember the year that I graduated from college and mind y', all, I was so broke. Like, the only reason I was even able to go shout out to my friend Brittany, who used to run a website called I Hate my publicist dot com, God bless her. I was only able to go because my friend Brittany, I told her that I wanted to go. I couldn't afford the flight. I was out of college, not working, whole marketing degree, but wanting to work in the creative field. I was interning in New York in a casting development team for a major casting company, but I wasn't making any money. It was an internship. And she was like, I have extra points, Southwest points for flights. I'll get your flight and then we can. And she was like, I already have a hotel room. Don't worry about it. When you get it, just throw it back to me. And I was like, are you serious? And she was like, yeah. And I was like, okay, cool. So I called my grandmother and I was like, hey, I'm going to this conference. It could really be helpful in me finding a job. Can I borrow some money to, like, get some clothes to go and, like, have money while I'm there? So she yelled at me for, you know, about an hour, but nonetheless, she supported it. And I went. And I remember the panel, One of the panels, the first panels that I went to was a panel about people creating online, specifically on YouTube. At the time, YouTube was so new, the first ever upload was published in April of 2000. 5. And I believe this was what if I graduated from college in 2014. So this had to be, yeah, like 2014. So YouTube was still, you know, a couple some years new. Like, people were still trying to figure out how they were going to use it. And. And honestly, I feel like it was more so people outside of music artists, like, I. I feel like music artists got it. They knew what to do with YouTube, but everybody else, like, I remember people were trying to figure out, like, talk shows and stuff on YouTube, and that was relatively new around the time that I graduated. Shows on YouTube and I. Unheard of, but Issa Rae had a show on YouTube called Awkward Black Girl. I mean, there was a lot going on on YouTube, don't get me wrong. But I feel like people still didn't understand it. Like, you still had to explain it. Like, when I used to reach out for interviews on YouTube When I first moved to LA, people thought I was insane, and I was still submitting them to outlets, but people were like, what? You're not on, like, like a. Like a network? Like, no, but she had an awkward black girl and she, like, she wasn't even famous at this point. People knew her because was so, like, viral and people were starting to, like, watch it, but she was not famous. And I remember going to the panel and listening to her speak and listening to her talk about just trying to figure out money and, you know, all these things in order to put Aqua Black Girl on tv, and it was just so fire. And then to see, you know, where she transitioned and how the deal came to hbo, like, hbo. I felt like I was a part of her journey. So when I say people don't talk about Insecure success enough, I just feel like people, unless you were, like, really closely watching Issa or you tried to do it yourself, you don't understand how hard it is to do what she did and. And do it well to the point where, like, she's. I mean, like, Emmy, not like, you know, all these things have happened for her and to her since Outstanding. She was, you know, Primetime Emmy Awards Outstanding comedy series in 2020. Outstandingly actress in a comedy series Issa Rae 2018, 2020, 2022. These are all nominations. Notable nominations Outstanding Supporting Actress in a Comedy Series Yvonne Origi, who plays Molly. Insecure Golden Globes Best Performance by an Actress in a Television Series, musical or Comedy issa Ray in 2017, 2018 and 2022. I mean, the list goes on and on and on and on and on. There's been NAACP Image Awards Nods as well, too. Like, I am just always in awe of her. So listening to this podcast and hearing her break it down, the first thing that they come out the gate swinging with is the fact that Tony Rock was supposed to direct the show. I cannot imagine insecure with Tony Rock directing it. Let's take a listen. Cause Issa couldn't either.

[Issa Rae]

Like, HBO really wanted Chris Rock to direct.

[Kim Coles]

Cause he was fresh off top five.

[Issa Rae]

He was fresh off top five, but he was based in New York. And I was very much like, this is a LA show. And they flew me out. It was my first time flying first class to go meet him. He was staying in, like, the Mandarin Hotel. And he was also, like, freshly going through a divorce. And, you know, I was initially excited about the prospect. Cause I love top five. Obviously, Chris Rock is a legend, but when we met, there was, like, a couple things that were evident. And so I left. I spent the night in that luscious hotel.

[Kim Coles]

Put on the robe and slippers and

[Lauren LaRosa]

just kind of, like, held yourself emotional.

[Kim Coles]

Yes.

[Issa Rae]

Like, oh, no, they really want this. And I don't think he's. He wants this, and he's ready for it right now. And so when I flew back, they were like.

[Kim Coles]

And it was also, we can shoot in New York and fake la. Fake New York for la. Which is like, you can't do that. Yes.

[Issa Rae]

He wanted to fake New York for la. He was like, we'll shoot the exteriors in la, but everything else can be in. And I was like, but they're window. Like, but I don't want to show off la. And what about exteriors Went back to hbo. They were like, how did it go? He seemed like, it went well. He's into it. And I was like, oh, man, great. And I was telling my managers. I was like, yeah, I don't think he's right. And I talked to you, and I was like, this is. This just doesn't feel right. And so ultimately, you said that brilliant thing where you were like, things have a way of working themselves out. And I was like, cool. And I remember I still called him, and I went to voicemail. And when I hung up, he had called me at the same time, left me a voicemail, and was like, hey, I'm going through a lot right now. You know, I just want to let you know, like, thank you for considering me for the podcast. But, like, I just can't do it.

[Lauren LaRosa]

Right, Right.

[Issa Rae]

And I was like,

[Lauren LaRosa]

but I do think that it's a testament to Issa. Again, we go back to what we opened up this podcast episode with. With understanding, like, what was the reason in the beginning, and her really understanding what her reason was, what her story is she wants to tell. And sticking to that now, it worked out where she didn't have to break Chris Rock's heart. And let's take a listen how God worked that all out.

[Issa Rae]

And then years later, after the show aired, was in Atlanta at a party, and Insecure was, like, in his second, second season. And I saw him, he looked great. He looked happy. And he was like, yo, insecure is great. And I was like, oh, man, thank you so much. That means a lot coming from you. And he was like, I would have

[Kim Coles]

fucked your shit up.

[Issa Rae]

I was like, validation. Thank you so much, Chris. Thank you for Chris, too.

[Lauren LaRosa]

Like, admit that that's.

[Kim Coles]

That's. That's dope. You know what's funny about that story you just told, which I do think is specific to. I think the way black people sometimes have to move in this business versus our counter, our counterparts, which is sometimes when you, like. Like, you think you just have to kind of accept what they tell you.

[Issa Rae]

Yeah.

[Kim Coles]

And. And because you're so, like, I got this opportunity. I don't want to mess it up. So even if I don't feel it's right, I'm kind of going along with something that I know kind of in my gut isn't right.

[Lauren LaRosa]

But.

[Kim Coles]

Whereas sometimes our counterparts are like, no, I'm not doing that. And there's no blowback to it. But we have to think a lot of times, if I say this now, how is that? Am I gonna come across like this? You gotta do all this math.

[Lauren LaRosa]

Yes.

[Issa Rae]

I have to decide, like, okay, I'll accept this now so that maybe I'll be granted grace later to get this, you know, other. And you still operate like that. But when something is so clearly wrong, like, you just have to speak up, man.

[Lauren LaRosa]

Like, I. Yeah, I can't even imagine having to be the person that would have made that phone call if it did not work out like that. Like, I literally cannot even imagine that. Because you hear Issa say, even today, there are times where you gotta take certain things on the chin. Cause you're like, man, as a black creative in this space, in this entertainment realm, doing all these things now, especially at a high level of where she's at, you know, you feel like, all right, like, if I don't do this this way, the opportunity will be going. That is such an anxiety point. Like, you're always thinking about, if I wake up Tomorrow. And because of one decision, one, no one, whatever, all of this just stops. And I think anytime black people are in a space where we're being treated as a unicorn, either because we are, because at that level, the others haven't seen it yet because we know we're not like, we know it be hella us. Like, you know, you can think of people in your life right now that, that have been dope at what they're doing. They just don't have the platform. But to a certain extent, I think success is really garnered because it's like there are a lot of people that are talented that can do something, but everybody that there's like a it factor that everybody doesn't have. And I think everybody's it factor for the people who have it is completely different than the next person's. So to a certain extent, you are kind of a unicorn. But I hate saying that about black people because it's like, I don't know, I just don't like the whole, like, black people and we got to be magic to make it work. But anyway, I digress. There's. I don't know, there's such a pressure point at that. Like when you're succeeding at a certain level, you know, as a black person, as a space in a space, or even if it's just not like a black person in a space, when you are extremely successful in a space and you're doing it at a certain level and you're accomplishing things for a company or within, you know, a certain area of your life, there's a pressure to top yourself, but also to keep it going because things change around that success. Your lifestyle changes, the bills change, the people depending on you change, the way you look at yourself changes your level of here's what I can accomplish, so here's what I have to keep accomplishing. Changes, right? So now you trying to figure this all out on a whole different. You know what I mean? A whole different situation. Like, completely different. It's more so like the. The conversation about, like, upkeep, but also understanding that, like, there's always this feeling of like, I might not get let back in.

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[Cal Penn]

hey everyone, it's Cal Penn. I'm the host of Irsay The Audible and iHeart Audiobook Club. This week on the podcast I am sitting down with Ray Porter, the narrator of Andy Weir's audiobook project Hail Mary Massive sci fi adventure about survival and science and what happens when you wake up alone, very far from Earth.

[Ray Porter]

I really had to make a decision because I caught myself getting that frog in my throat and starting to get teary as I'm narrating some of these sections and it's like okay, yo yo yo, is this indulgent? And I really thought about it. I was like no. At this point it would Kind of be betraying the trust the author and the listener have in telling this story if I don't go through it. But there's places in this book that deeply, emotionally affected me and I left it on the mic. That's great because it served the story. People will say like, oh my God, I cried at the end. It's like, yeah, dude, me too.

[Cal Penn]

Listen to Irsay, the Audible and iHeart audiobook club on the iHeartradio app or wherever you get your podcasts.

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[Lauren LaRosa]

about the casting and I thought that this was important to include because I think that this was another really brave. Nah, I'm sticking to my guns. Moment by Issa Rae where she talked about, you know, even with keeping her and Molly as the leads of the show was intentional. Let's take a listen.

[Issa Rae]

I had a very, I had very specific types in mind. You know, like again, this is based off of a real best friend of mine. And so my best friend is actually a dark skinned, beautiful black woman, straight hair. Like I had a specific archetype and I remember, you know, even in casting choices, I was very specific. I was like, I don't want to do the, oh, dark skin, light skin combination that's always in these black shows. I'm like, these are two dark skinned leads because this is true to life. And I was very specific about that and that, you know, casting would still send send tapes and I'd be like, no and no shade. But I was just like, I'm just not looking at, I'm not looking at this. And then for Lawrence I was open. But do you remember our first casting meeting? We met with these initial when we're interviewing casting directors, the first ones that we interviewed were like, we're thinking of for Lawrence, like a Jay Ellis type. And I was like, he's like kind of too handsome. And I was like, nah. And we ended up not hiring those casting directors and we went with Vicki Thomas and crew and J. Ellis ended up auditioning and I was still like, mm, mm, he's great, but I don't know. And then that was still in my mind. But casting generally, I'm getting ahead of myself. Like, outside of Molly, I was generally open, but I wanted to have, like, real people. Definitely not celebrities.

[Lauren LaRosa]

Yeah, man. I was watching this video on Instagram. It came across my feed. There's a adult photographer. I believe he's out of la. His name is JPW Photo. I've actually, like, I've been following him for some time. He has really, really dope work. So he posted this video. We're gonna play some of the audio, but I want to give you guys some context since you can't actually see it. So in the video, he has Anok, who is a world famous supermodel at this point. We have Drew Ski, we have Ryan Coogler, and we have Keke Palmer. And he's talking about, you know, how bold, new and fresh you have to be as a creative during this time because you're learning in front of the world while also building empire and business. And it really made me think of Issa Rae. Let's take a listen to the video and then we'll come back.

[JPW Photo (Creative Industry Commentator)]

Why not you? Seriously, what if I told you that you could be up next? Because when I saw Drew Ski's Erica Kirk video, which had me dying, laughing, it made me realize something, that the next generation of icons is already here. And we're literally watching those icons get built in real time. We probably just don't realize it yet because we're living in it. But years from now, people are going to look back at this era the same way we look back at generations before us. And I think what's so refreshing about somebody like Drew Ski is that he's willing to go the extra mile with his bits and takes the risk comedically because he's that hungry. And that hunger really matters, because a lot of the legends that came before us, they were hungry too. But they built what they needed to build. They became icons, millionaires. They built empires, businesses, families. They're put up and the legacies are now cemented. Now it's time for this generation to push things forward. And you can see that shift happening everywhere, especially in this digital space. And honestly, I think it's beautiful watching the torch get passed with grace and going back to creative lineage. I think about the lineage of, like, Eddie Murphy or Martin Lawrence Todruski or Angela Bassett to Keke Palmer or Spike Lee to Ryan Coogler or Naomi Campbell to a Knockey Eye.

[Lauren LaRosa]

Yeah. And it really made me think of Issa Rae, because, I mean, I model. When people ask me, like, you know, who are people that you look at in the industry and doing things that you want to do? She's always one of the people that I name and has been for a long time, and even not just because of her professional accolades. Like, I feel like just her as a person, and I've never met her. And if this episode gets to Issa or anybody that knows her, I would love to meet her and would love to sit down and interview her, anything, even if she don't want to get on camera, interview, would just love to shadow her for a day, a week or two. I just think she's one of the brilliant minds. Because I do think that it. You know, it's like we have a new genre and era of celebrity. And with this new era and genre, not even just celebrity, but a new era and genre of business men and women, of. Of professionals, of shoot. Like, anything that exists in what people are successful at, like painters, dentists, therapists, psychiatrists, like, everything is different nowadays because everything is hyper social media and hyper Internet, and all of social media and Internet is driven off of people and clicks, which results into ads and engagement, which equal the way that people make their money. So because of that, that there is such a hyper, you know, need to critique and have conversations online and do all these things. So it's like you're literally learning this new space as you go in front of the world, as the world is critiquing you very, very loudly, which also can affect, either in a negative or positive way, your dollar. Unless you learn how to fail and achieve in front of the world and use all of it to teach yourself things and build a business. And I feel like it takes very strong people to be able to do that on a high level, right? Because, I mean, I'm talking about, like, Drew Ski, Kiki Palmer, right? Like, these are people. Drew Ski has skits that are viral, like, every other month. Every month. And I mean viral to the point where, like, Fox News pundits and CNN and us over here on the pop culture side are having, like, he calls this conversation that, like, literally shakes the world today from an Instagram and YouTube upload of a sketch comedy, by the way. Right? But that is what comedy did years and years ago and does what a lot of people nowadays with, like, the Dave Chappelle's, you know, but, like, he's doing it in a very different way than the Dave Chappelle came up doing it so he's learning so much in real time while also filtering out critique noise or whatever, but staying very true to his core and to his process of always remembering the game plan. Like, what was the game plan in the beginning? What was the appeal? Why was it that where. Where do I live in all of this? Like, you know, because now things are changing, but, like, who I. I'm. I am who I always been, and how do I continue to express that, but elevate the way that I do it in the look and in the conversation, right. And in the things that I tackle. Issa Rae, for me, is a person that would. I would totally throw her in this conversation because everything she's figuring out to do, even with this podcast like Living Single, you know, they had a rewind podcast as well, hosted by Kim Coles and Erica Alex. And I thought that that was amazing because we love and breathe those shows. And we don't know if we're gonna get any more of Living Single on camera, but at least we can get the podcast and. And talk through it with the cast. And I think, you know, if I'm just inferring here, but I'm assuming Issa Rae saw something like that, understood the value of it, just because number one of, she always seems like she's the person that wants to inspire the next creator. But also she loves the art, and I feel like her art, even if she doesn't know it, it teaches other people. So it's taken back to her, like, why of things like when I first discovered issa Rae on YouTube with Akra Black Girl, not only was she doing Aqua Black girl, but her YouTube channel. Even then she would platform other series that were like smaller series so that she could, like, showcase up and coming actors, writers, directors. I know she just dropped, and this was years ago, she just did, you know, just this year, dropped a shorts whole series on TikTok that is doing extremely well. So again, always going back to, like, what was the plan from the beginning? But being able to remember that while building a foundation by doing all of it in public, while building real business that leverages beyond just one or two viral moments, child, you gonna need to really sit down and relax every Sunday and be optimistic about every Monday when you really lean into that bag, because there's a lot that comes with it to. To whom much is given, much is required. Well, that conversation is live in full if you guys want to go and check it out. With Issa Ray and Princess Penny on YouTube, it is called Block Party B L O C C party. It's on the Hooray Media YouTube channel. That's Issa Rae's production company, Media Company. So go check it out. I'm Lauren LaRosa again. This has been another episode of the Latest with Lauren LaRosa. This is your daily dig. You know all things pop culture, entertainment news, and all of the conversations that shake the room, baby. I tell you guys, every episode y' all could be anywhere with any old body talking about all of these things. Things. But y' all choose to be right here with your girl and I appreciate you. I'll catch you in my next episode.

[Cal Penn]

Hey everyone, it's Kel Penn. I'm inviting you to join the best sounding book club you've ever heard with my podcast, Hearsay, The Audible and iHeart Audiobook Club. Every episode, I nerd out with amazing guests and dive into the best new audiobooks available on Audible. It's the book club for your e ears. Listen to Earsay, the Audible and iHeart audiobook club on the iHeartradio app or wherever you get your podcasts.

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[Wheezy (Wheezy WTF Host)]

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[Lauren LaRosa]

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[Lauren LaRosa]

This is an iHeart podcast.

[Issa Rae]

Guaranteed Human.