Issa Rae Is Having a ‘Good-ass Summer’ 

Photo-Illustration: The Cut; Photo: Jabari Jacobs

It’s summer vacation for Issa Rae … kind of. This week on the In Her Shoes podcast, the writer, producer, and comedian sat down with the Cut’s editor-in-chief, Lindsay Peoples, to talk about taking breaks and taking care. Known for her bevy of beloved comedy series, Insecure, The Misadventures of an Awkward Black Girl, and, most recently, Rap Sh!t, Rae is being more intentional about resting between her many projects these days. Not least because Rae also runs Hoorae, an umbrella production company that includes ColorCreative, a talent-management company dedicated to supporting diverse creators. For Rae, the company is about allowing creators to tell stories across different spaces. Now in her “mogul era,” Rae is building a multidimensional empire and bringing lots of talented people along with her.

Rae tells us about going out with a bang on the final season of Insecure, being nominated for an Emmy, and learning that she’s “particular” after working on her new show, Rap Sh!t. There are a lot more stories that she has to tell, including one in the form of a finished movie script, which she’s also working on getting made right now.

To hear more about why Rae feels “lighter” these days, plus her TV recommendations, listen below and subscribe for free on Apple Podcasts or wherever you listen. You can also read the full transcript below.

This transcript has been lightly edited for clarity.

Lindsay Peoples: Welcome to In Her Shoes. I’m Lindsay Peoples, and I’m editor-in-chief of the Cut. For the next few weeks, I’ll be taking over this feed and talking to people we at the Cut love and admire or just find interesting. We’ll explore how they found their path, what got in their way, and how they think about bringing others along now that they’ve arrived.

Not only has Issa Rae appeared on the annual Time top-100 list of the most influential people in the world twice, she’s also redefined the half-hour comedy for a generation. The actress, writer, producer, and comedian first garnered attention for her YouTube series Awkward Black Girl, and soon went on to co-create and star in the HBO series Insecure. She’s also starred in popular films like The Hate You Give, The Love Birds, and most recently starred in the forthcoming film Vengeance. Issa continues her bad-bitch renaissance in full force with the debut of her HBO show Rap Sh!t. I was honored to be able to talk to Issa about her rise to the top, why seeing female friendships unfold on the screen is so important, and what she has planned next. Thank you so much for joining us today, Issa. I’m so excited to talk with you. So this show is called In Her Shoes, so I have to ask, what shoes are you wearing right now or what are your favorite shoes to wear?

Issa Rae: I’m wearing Stuart Weitzman shoes.

Lindsay: Oh, fancy.

Issa: They’re a glittery gold. And Stuart Weitzman is my favorite shoe brand to wear, mostly because I have big feet, and they make shoes my size, and they’re cute shoes. Sometimes when you have big feet, they just give you orthopedic shoes.

Lindsay: This is true.

Issa: So I’m grateful to Stuart Weitzman.

Lindsay: They can’t see you, but you look really fly. You’re wearing all the beautiful summer colors.

Issa: Thank you. I’m really feeling summer. I’m having a good-ass summer so far.

Lindsay: That’s good. What are you doing to have a good-ass summer? I’m curious.

Issa: I’ve been traveling, I’ve been living my best life. I’m really happy. I’ve just been really intentional about breaks. I’ve been taking care of myself. And yeah, I just feel good.

Lindsay: Like non-work vacations, or have you been working?

Issa: Workations, but work and play. I’m putting play in my work a lot.

Lindsay: Okay, good. I mean, I aspire. I need to do more of that.

Issa: What shoes are you wearing?

Lindsay: Chanel sandals.

Issa: I’ve been looking for sandals like this. Again, on my Bigfoot shoe quest, I’m trying to find the right ones. There are these lavender Gucci sandals that I really liked. I’m not even into that. And they were a size five in women’s.

Lindsay: Yeah, that’s impossible. I wear these Chanel sandals all the time because they’re like dad sandals but they’re chic. Let’s start, obviously so much is happening right now and I want to talk about Rap Sh!t, Insecure, but now that you are incredibly, incredibly, incredibly successful, when you look back at it, are there any aha moments from the beginning, from the Misadventure days or even before that, that are aha moments that are connecting to things that you’re doing now?

Issa: Well, for sure The Misadventures of Awkward Black Girl was a training ground for me. To be in a show and to run a show, my very first writer’s room, I didn’t know I was in a writer’s room, was in The Misadventures of Awkward Black Girl that I remember, it was me, Amy Aniobi, who writes on Insecure; Tracy Oliver, who has a show, Harlem; and OC Smith, who is a writing teacher, and that community of just Black women being able to vent, and create stories, and laugh was so much of the groundwork for Insecure and even to Rap Sh!t. Black women are leading that front to back. And I just find so much comfort in working with us.

And then, beyond that, it’s always just come down to trusting my voice, and I’ve always doubted that. Even in Awkward Black Girl, the second season, I thought that maybe people wanted to see less of me and put more characters in the front and in the foreground. And Insecure, Prentice had to be like … Sometimes I’d be like, “Okay yeah, let’s do this.” And he’d be like, “No, this show is about Issa,” not necessarily talking about me, but Issa Dee. “And so we need to center her.” And that’s hard for me to do. So now, being on the other side of it, I recognize how important it is to make sure that I’m not diminishing anybody else’s voices.

Lindsay: That’s beautiful. When you think about it now, what compelled you, as young Issa, to really want to write, and tell those stories and the stories that you’re telling now?

Issa: Young Issa, when I think about that, I think about college me, honestly, high-school me, and what I wanted to see, and what I was inspired by, and what I was motivated by. What would make the butterflies in my stomach rise up and ruffle. I just love seeing us and all our images, I love seeing us fall in love. I just love our beauty, and so that really makes me tick. And I just love how we react to things so uniquely. Anything that has to do with us and framing us in a very specific way, I want to be a part of.

Lindsay: Yeah. How does it now feel to be Emmy-nominated final season of Insecure, knowing that the show was ending?

Issa: Great. I mean I think everybody wants to go out with a bang and with season four getting so much acclaim, that was rewarding because we’d always been saying season three going to be cool, but season four is about to be lit. We have so much story to tell in season four. And so the fact that it resonated with people in such a great way was amazing. And then now, to get three nods in our final season when we aired in December, I thought people forgot about this show, there’s so much good stuff out there.

Lindsay: I think about Insecure every day. Every day. I said, before we started recording, I’m going to be annoying about this, but I think about it all the time.

Issa: That’s so wonderful. And I hope it lives positively in people’s hearts.

Lindsay: Absolutely.

Issa: What do you think about?

Lindsay: I miss the comfort of it.

Issa: That’s so nice. That’s such a huge compliment.

Lindsay: Growing up, when I used to watch Family Matters and Fresh Prince when I came home, because my mom was like, “You get an hour of watching TV and that’s it.”

Issa: Yeah, same.

Lindsay: It just makes me feel warm, and that’s what I miss.

Issa: That is so nice.

Lindsay: But I know for a creative, it’s like I’m ready to move on to a different project, so how was that also just to experience that personally of people really missing it and not ready to move on, but you personally being like, Okay, I’m ready to close this chapter?

Issa: I always heard about how, by the time musicians release albums, they’re already tired of the music on there. And at first I was like, What? That’s crazy. And then I get it. Insecure, I was ready to let it go for a long time and I appreciate that people love it, but as a creative, I want to know that I can do more. I don’t want people to think I can just do that, people to only want that from me. And I just want to tell so many other stories. And I’m really proud of this show, and just strongly believe in not overstaying a welcome and walking away when you’re out on top.

Lindsay: Yeah, that’s real. We know that it was an upward-hill trajectory from Awkward Black Girl to Insecure, now with Rap Sh!t. I think we can curse on this podcast. I’m pretty sure we can. They’re not going to bleep it.

Issa: What? Shit, Rap Sh!t. Are we talking about Rap Sh!t right now?

Lindsay: I saw on TV the other day you were talking about this —

Issa: I know, it’s a struggle. People won’t even say the title, which it’s to be expected, actually. I don’t know why I’m acting offended.

Lindsay: It’s fine. But we won’t bleep it. Tell me about the thought process of wanting to do something completely different, obviously another show for HBO about Black women, but what did you feel were the challenges in creating this show?

Issa: It’s told from a unique lens, we used the perspective of social media a lot throughout the first couple of episodes, and it is a lot younger, and it is specifically set in the music industry. And about female friendship, but it’s still an odd couple dynamic. And I really just wanted to explore this particular time period, what it takes to be a creative, what it takes to rise, what it takes to be yourself. And it’s an exploration of all those things specifically through this time, during this time.

Lindsay: Yeah. Obviously music is such a big part of the show and I know that you’ve produced a lot of things running your own record label, all of that. Where does that come from and why is that so important to you also?

Issa: It’s just, music is such a great medium to tell stories, music is so universal. Everybody feels songs differently, everybody feels albums differently, everybody connects to artists differently, and I just think it’s so powerfully special. And so this particular show appealed to me because again, I wanted it to feel like this time and I wanted the show to feel like how female rap music makes me feel. And then on the Raedio arm, it’s again part of my storytelling. I’m so passionate about artists, they are creators, and I wanted to have, first and foremost, a label that was artist friendly, where they could own their masters and where we could also support them as multi-hyphenates, because if you’re a storyteller in one space, you can be a storyteller in many spaces. And then that’s also developed to just how can we be an audio-everywhere company? And so that’s taking music but sound very seriously and treating that as an industry in its own right.

Lindsay: Yeah. I mean, when Insecure first came on, I could tell that you loved music because the playlist was just crazy. It always obviously would go with the scenes and sometimes I’d be like, This is now my new favorite hype song. What is your new favorite hype song or favorite song to listen to right now?

Issa: My new favorite hype song is “Break Up to Make Up” by VickeeLo. It has a New Orleans bounce beat and it is so great.

Lindsay: VickeeLo, okay.

Issa: That is my hype song.

Lindsay: I’m downloading it.

Issa: Okay. On my little runs, my walks have progressed to runs, and that always gets me pumped. That and an underrated album, the Jay Z and Beyoncé album.

Lindsay: Oh, that’s not underrated. I love that album.

Issa: I feel like it doesn’t get flowers. Lemonade was amazing. I mean not Lemonade. Why am I sucking with —

Lindsay: I see it, because it was the one they shot in the Louvre.

Issa: The first one that came out. Yeah, the one they shot in the Louvre. The breakout song. Somebody knows, but that one, but “Black Effect,” it always gets me.

Lindsay: Everything Is Love.

Issa: Everything Is Love.

Lindsay: Yes.

Issa: But what was the first single that they dropped? That Quavo was doing all the sound effects on.

Lindsay: “Apeshit.”

Issa: Thank you, “Apeshit.” “Apeshit” and “Black Effect” get me. You don’t think it was underrated?

Lindsay: No, I love that album.

Issa: Okay. I feel like people don’t reference it —

Lindsay: Yeah, they don’t reference it enough, but I love that album. It reminds me of summer.

Issa: Yes, a good summer.

Lindsay: Yeah, very good summer. I have Bey on repeat right now for my workouts.

Issa: Which one?

Lindsay: I love the one with Lil Jon. Where she’s like, “She’s that bitch, fuck that bitch.” I’m cursing a lot because we can curse in this one. Sorry.

Issa: I think it’s my influence.

Lindsay: Anyway, I’ve heard you say a lot that you are in your mogul era. What does that mean to you and why is it important to you? And I love to see a Black woman say this publicly because I think it’s so important.

Issa: Yeah, I’m cringing hearing you say it back to me.

Lindsay: No, don’t cringe. I think it’s really important for young Black people to hear.

Issa: I just want to embrace the fact that I’m running businesses in multiple industries, and I aspire to do it well, and I aspire to be competitive with the greats. And I have looked up to the Oprahs, the Diddies of the world, and it felt intangible to me, and I feel like I’m very much touching it. So I’m claiming it now so that I can continue to build.

Lindsay: I mean, all that you’re doing with Hoorae Media, what does that entail? And what are your dreams or hopes for that?

Issa: Hoorae is an umbrella company. We have our film-and-television division, which works with HBO, HBO Max, and Warner. We have Raedio, which I mentioned is the audio-everywhere company in our label. We have a management company called Color Creative, and that’s representing artists on the film-and-television side, and beyond, and then just other different arms, including our digital division. Each of those arms have heads and it really just is about trying to be a synergistic company, self-sustaining, and trying to make culture in all aspects, trying to make sure that we are creating conversations, that we are leaving imprints. And hearing you say that we’re your comfort show, I want that from all the mediums that we touch.

Lindsay: Yeah. Were you nervous at all with Rap Sh!t coming out because of how people have felt so strongly about Insecure? Were you nervous about the next show coming out, and worried?

Issa: I had some anxiety, I think that’s normal for me, but with this show I was less anxious because I’m not in it. There’s just something about being in it that makes you feel like are they going to hate me?

Lindsay: We would never.

Issa: Never know. But with this, I’m so confident in the cast, I’m so confident in the story that we’re telling. I believe that it’s a fun-ass show. I will argue that now. So I’m not as nervous. I think if you take anything too seriously, I think that’s where this came from as well, I feel like whenever there’s Black content, there’s always a pressure for it to be super message heavy or we talk about traumatic, and this, I keep describing it as a summertime show because again, that is what it is. It’s a feeling, it’s representative of riding in a car with your girls, taking a rogue trip, and that’s what I want the show to feel like.

Lindsay: Yeah. In managing that, though, even though you’re not on the show, you still have all these other ventures. How do you handle that? I mean, you’re only one person. Do you feel like you are taking enough time for yourself? Do you feel like it’s just game time and you just got to do it?

Issa: This year, I’ve been so much better about taking time for myself, and I feel it. I just feel lighter. That is because Insecure is over, low key, but because Insecure was a 9 to 5, basically, in addition to and on top of, and now I don’t have that block of time, that eight to nine hours a day taken out of my schedule every single day, in addition to then having to shoot it for 15 hours a day. And so now, I get to be more focused on what I pursue, and I’ve been so good about taking weekends, in some cases, and taking vacations.

Lindsay: Yeah. I mean you have to because all of these things are great, but I think also people don’t realize just the toll that it takes and how much energy it takes to make great work continuously over time. So I really admire you for that, for sure.

Issa: Yeah, shout out to people who make 22 episodes of TV because I can’t imagine. There’s no way. Quinta’s out here making that and I can’t.

Lindsay: I love Abbott Elementary so much. I’m so happy for her.

Issa: So happy for her, so deserved, and I cannot believe. I was like they’re back, they’re literally shooting again, and it just ended. Anyway, that’s a lot.

Lindsay: No, it’s a lot, but it’s an incredible show and I’m really excited for them for Emmys.

Issa: Same.

Lindsay: Obviously, a lot in your shows is tied to the dynamic of female friendships. Are there any female friendship dynamics that you have yet to explore that you want to or you can’t tell me because you are currently exploring them in the show that you’re writing?

Issa: I love siblings. I love the friendships between siblings. I think that’s more of a familial angle that can or cannot be a friendship, but I just love and plan to explore those dynamics a bit more. Being the middle of five, I have tons of sibling dynamics to explore, so I’m actively thinking about the best way to do that next.

Lindsay: I would write something about my sister tomorrow. She’s crazy, but I love her.

Issa: Is she older or younger?

Lindsay: Older. Seven years older than me.

Issa: So did you watch, observe, and avoid or did you follow in her —

Lindsay: Absolutely. No. And they had told my parents that they couldn’t have another kid. So she was very, “I’m so excited to be an only child,” and then my mom had me and my parents were really excited, and she pretended to lose her vision. My parents actually thought that she had lost her vision, she was seriously pretending. And they took her to all these doctors and the doctors were like, “No, what’s going on? She’s faking. She can still see.” And they were like, “Oh no, we’re having a baby. That’s literally all that’s happening.” And so they let my sister name me as a barter so that she would stop pretending that she was losing her vision, and that’s why my name is Lindsay.

Issa: First of all, your sister is an incredible actress.

Lindsay: Yeah, she really is. The dramatics never stopped, but she’s my favorite person.

Issa: What’s her sign?

Lindsay: She’s an Aries.

Issa: So many Aries in my life. Wow, Aries can hold a grudge.

Lindsay: Oh, yeah.

Issa: I was just talking about that the other day. Boy, does she hold a grudge against your parents. “I’m now blind and I refuse to see.”

Lindsay: It was crazy, but I love her.

Issa: That’s incredible.

Lindsay: No, the sister relationship would be fun so I’m excited if you do that.

Issa: Okay, I’m stealing that.

Lindsay: Have you learned anything about your creative process that has shifted over the years or changed now with Rap Sh!t versus previous projects or movies that you’ve worked on as well?

Issa: That I’m controlling. I didn’t know. I wouldn’t describe myself in that way at all, but I discovered doing this latest project, oh wow, I am controlling. But in some ways, you have to be.

Lindsay: Type-A controlling?

Issa: Yeah.

Lindsay: Oh, interesting.

Issa: But only when it comes to these specific projects and it really comes to once I realize, Oh, this is wrong, this is not the way I envisioned it, and this is not the way that I envisioned it, but it’s better or this is not what I envisioned and okay, I can go with this. If I see anything that just doesn’t align and feels incorrect, and then I just go into a certain mode and then I’ll bulldoze through. And I didn’t know that about myself. I always consider myself pretty easygoing, but I think that’s developed over time. And I would define it as taste now and being particular.

Lindsay: I love that. I’m going to use that.

Issa: I just have taste or I’m particular. Someone described me as that and I love that.

Lindsay: Yeah. I mean I don’t think that’s a bad thing. That’s a good thing.

Issa: Yeah, I guess, but I think it’s just the way that you go about it.

Lindsay: Yeah. Your tone and how you present it, 100 percent. I see that. Have you had a second to take a step back and take stock of all your success yet?

Issa: Yeah, this year. I had a moment, I journaled it, where I was like, Oh my God.

Lindsay: Oh, you journal.

Issa: I have a journal.

Lindsay: How often do you journal?

Issa: I try to do it every day. It usually probably averages out to every other day.

Lindsay: Writing or voice notes?

Issa: I hate voice notes.

Lindsay: Oh, I do voice all the time.

Issa: What? And do you actually listen back?

Lindsay: Yes. And every time I do I’m like, You are definitely unhinged. That was crazy.

Issa: Wait, do you do, “Travelers log?” What do you do?

Lindsay: No, I do it on an app that you can type, or you can put photos in, or you can do audio.

Issa: Evernote?

Lindsay: No, it’s called Day One.

Issa: Oh, okay.

Lindsay: And that is not sponsored. I really use it. I like it because sometimes I don’t know what to say or how to say it, and so it’ll take me a while just to get there, but it also transcribes it for you. So then it types it out after you’re done.

Issa: Do you look at it like, What the fuck was I talking about?

Lindsay: Yeah, all the time.

Issa: Or do you always know?

Lindsay: No. But you’ll know. It’s just interesting to hear your voice inflection on a day that you’re just full of anxiety, you’re like, Oh my gosh, you shouldn’t have done XYZ.

Issa: I can see it in my handwriting, I was going through it that day. I didn’t try. But I love revisiting things. Everything is in my notebook and it just really helps me. That’s my therapy at the end of the day. But I don’t remember why we got on that.

Lindsay: I was saying about taking stock of now, all of your success, and you were saying that you journal it.

Issa: Yeah, I journaled about a very particular moment and just how grateful I was, and just recognizing how far I’ve come and just what I’m able to do, how I’m able to live, who I’m able to surround myself with. I just feel incredibly blessed.

Lindsay: Yeah. Do you feel like it’s now more fun to be in the industry because there are a lot more Black people that are having opportunities to be able to do things? It looks like it. At award shows or just different events, it looks like it’s more enjoyable because it is more diverse, and it is, I think, different groups of people that are just coming up, like we were talking about Quinta earlier, that are on the same wavelength.

Issa: It’s so much fun. Even I was at ABFF and I was like, I guess I do want to throw a little yacht party out there because there are so many shows and they’re

Lindsay: A little yacht party. Casual.

Issa: There are just so many Black shows and Black artists that were out there, more than I imagined, because obviously there are a lot more. I’m not going to say there are so many because we have so many more to go. And that was exciting just to meet new people. The only anxiety I get is there are a lot of shows and I have not watched all of them, so I may see someone and they may be famous from their show, and I don’t know them yet because I haven’t watched the show, and I get embarrassed. I’m just like I don’t know.

Lindsay: What are you excited to watch that you haven’t yet?

Issa: I don’t want to even blast myself because I’ve pretended to know people.

Lindsay: No, I know. I’m curious of your personal TV taste of what to watch or it could be something that you have already watched that you really —

Issa: I watch dramas all day. I love thrillers. I’m raving about Severance.

Lindsay: That was a good show.

Issa: It was a great show.

Lindsay: That was a good show.

Issa: What an incredible season finale. I just watched the first episode of The Rehearsal, the Nathan Fielder show.

Lindsay: Oh, I have not seen that, but I heard.

Issa: You have to watch The Rehearsal if you love cringeworthy shit but also brilliance.

Lindsay: I do. That’s up my alley.

Issa: I watched FBoy Island too. I watched a lot of dating reality shows like that.

Lindsay: Yeah, Love Island, absolutely. My favorite.

Issa: What are you watching?

Lindsay: This show that I watched that I really loved, oh man, her mom was a murderer. I really got to find it now.

Issa: Her mom was a murderer?

Lindsay: Yes.

Issa: Sold.

Are you looking through your most recent watches?

Lindsay: I’m literally about to call my sister and ask her because I have to know now, because she’ll know.

Issa: Oh yes, I love a live call. This feels like a radio show now. Is she going to pick it up?

Lindsay: Maybe. She’s very corporate. She runs HR.

Issa: Oh, she has to be.

Lindsay: She wears suits every day.

Issa: Oh, sis.

Lindsay: Oh, she’s so annoying. Wait, so I found the show. It’s called Pieces of Her. It’s on Netflix, starring Toni Collette. It’s about a woman who pieces together her mother’s dark past after a violent attack in their small town that brings hidden threats and deadly secrets to light. I loved this show so much. My sister had told me about the show because she watched four episodes and she was like, “You should start watching it and watch it with me.” And then I finished it before her because she’s one of those annoying people that tries to binge watch a show but doesn’t actually binge watch it in a respectable amount of time. So everyone should watch that show, it was great. Let’s talk about what you want to do next that you can talk about that’s coming up or that’s coming out, besides Rap Sh!t, or that you’re excited about.

Issa: I wrote a movie.

Lindsay: You say things so casually.

Issa: What?

Lindsay: That’s the problem.

Issa: But it’s literally my job —

Lindsay: “I wrote a movie.”

Issa: — to do this. What else am I doing?

Lindsay: I don’t even understand the timing on how busy you are and then writing a movie.

Issa: Well, movies take a long-ass time. I wrote this a long time ago.

Lindsay: How long did it take you to write this movie?

Issa: I do this all the time where I have a December vacation. The industry takes a break for two weeks, sometimes three in December, and instead of taking that break, I took it, but I was writing the movie. So the stress of having a deadline, like, “Yeah, I’ll have it the first Monday we get back,” and I did it. So that was right before the pandemic happened. And I’ve just been revising it, so now I’m just trying to find a director. And as soon as we do that, it’s ready to go. And I really am passionate about this movie. I have to get it shot this year or else I’m like well fuck it, let me write something else.

Lindsay: I love that attitude. Well, I’m very excited about that. Anything else for your ventures that are coming up, or the label or anything that you’re excited about?

Issa: I will plug that my coffee shop, Hilltop, is opening one in LAX.

Lindsay: Nice.

Issa: Which is huge for us.

Lindsay: When is it opening?

Issa: That’s a great question. I’m going to say this summer.

Lindsay: Okay. I was only asking because I’m coming out to L.A. in a couple weeks, so I’d like to know.

Issa: Oh, I mean unless you’re flying United. Are you a United flier?

Lindsay: No.

Issa: It’s in terminal seven. You said that with lot of disdain.

Lindsay: Sorry.

Issa: United’s not sponsoring this, so I’m not partial, but I’m proud. But I was like, Oh damn, I’m not even going to be up there because I don’t fly United, but I will make a point to go there.

Lindsay: That’s a really chic venture, though. I like that.

Issa: Thank you. And then Sweet Life season two comes out August 4. I’m really excited. I love that cast. It is a juicy season and I can’t wait for people to see it.

Lindsay: Is there anything we didn’t cover that you want to discuss?

Issa: Vengeance is a movie directed by BJ Novak, directed, written by, and starring BJ Novak, that comes out July 29. Very soon. And it is about a true-crime podcast but so much more and I love it. It’s funny as hell, it’s so smart and well written, and it takes place in Texas, for all my hardcore Texans out there.

Lindsay: Love it. Thank you so much for doing this. I so appreciate it.

Issa: Thank you. Thank you for having me always.

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