vulture festival 2021

Issa Rae and Yvonne Orji Reflect on 5 Years of Issa and Molly

A wine down with Insecure’s OTP.

Photo-Illustration: Vulture; Photos by Bobby Doherty
Photo-Illustration: Vulture; Photos by Bobby Doherty
Photo-Illustration: Vulture; Photos by Bobby Doherty

It was always about Issa and Molly. Even in the pilot episode of Insecure in 2016, Issa and Molly go through a full arc of loving, fighting, and making up when Issa raps about Molly’s broken pussy. Over five seasons, their relationship has been the through-line of the show: Men might come on your face and go, but friends are forever.

It was only fitting, then, to cap off the final season with a wine down at Vulture Festival with both Issa Rae and Yvonne Orji. We popped a bottle of bubbly and reminisced: Back to development and casting when Rae just wanted to be IRL friends with Orji. What was their first scene together? Who was the “big-name director” HBO wanted in the beginning? What was it like shooting season four’s infamous block party? It’s sad to see Insecure go, but it’s great watching them leave.

Below, you can watch the full conversation, read an edited excerpt of the transcript, or listen to the full podcast episode. Tune in to Good One every Thursday on Apple PodcastsSpotify, StitcherOvercast, or wherever you get your podcasts.

What has it felt like to watch the final season unfold?

Issa Rae: I mean, it’s always exciting to watch with people. We got to screen the first two episodes at our premiere, and to see people react to it live was great. And we did a screening in New York together. And then, the online reaction is always just [Laughs.] so much.

Can you speak on it?

IR: It’s crazy! It’s crazy because the thing about doing a show like this and representing a specific culture, representing Black people in a way, even though we’ve said we’re not representing the entire Black experience — we can’t do that — people still hold on to it, you know? And so you’re telling a very specific story, but people feel like, “This is my story! This is our story, and you gotta do it this way!” And literally, if you’re telling a story to a friend and you’re like, “So I did this and whoop-de-whoop and then I met them,” Twitter is the person that’s interrupting the story to be like, “But what about this? What about this part?” And it’s like, “I’m getting to that, just hold on.” “But wait, what about this character? You just left them out!” “They’re gonna come back! Just shut up and let me tell this story!” And that’s what it feels like to make a show and for Twitter to respond.

Yvonne Orji: I’ve enjoyed watching the redemption story of Molly S. Carter. It only took two episodes. I was like, “Twitter is a fake place that people go when they are hurt!” [Laughs.] It only took one episode: “Ah, Molly’s good! We like her again! She’s always been a good friend!” I was like, “What the hell?” All last year in the pandemic, I was slitting my wrists!

Tell me about starting the season at Stanford and deciding to reconcile and heal the wound. There’s a version of the show where that could have been the end of the show, where they come together, but you decided to start with that.

IR: We knew with this season coming to an end, we wanted to get them both in a great place. And we’d established — subtly, albeit, in season one — that the characters were friends from college, from Stanford. Amy Aniobi, who’s an exec on the show, and I went to Stanford together. She was a year older than me, but her reunion was coming up, and I’d gone to my reunion just a couple of years ago, and it’s such a great place to reconnect. And to have that as a set piece for the origin of Molly and Issa’s friendship, in addition to the reunion of their friendship, felt right and an exciting story for us to show.

Did you ever consider a college other than Stanford?

IR: Yeah. I didn’t want her to go to Stanford. It was a props mistake. In hindsight, I guess that was just being too literal, because I was like, “Y’all put a fucking Stanford mug in Issa’s room? Why would y’all do that? I didn’t ask for this!” But nobody saw that! [Laughs.] But I think over time, we were just like, “Okay, the characters went there.” I also don’t know where I would have wanted them to go if they didn’t go there, and it matches the real friendship story and some of the real people that it was based on.

But a lot of things were established back in season one, including Molly being in AKA. What do you make of it being a thing now in season five?

IR: Honestly, I think it’s new viewers — people tuning in and being like, “This is the show y’all been watching? Because they fucking up!” You know, it’s like that element. And people do tend to pick this show apart. I think that’s also a hobby of watching the show: “Let’s see what they did wrong this week!” But it’s not everybody. It was a small subset of people. And I don’t think that responding helped, so it amplified it in a way. So you know, I think both sides are at fault here.

YO: But I think they’re still watching, so …

IR: I don’t know.

YO: Cheers. I’ve been watching. They watched last week.

IR: Shoutout to AKAs! We love you!

YO: And the Divine Nine, all y’all, because Lawrence is Kappa!

IR: No, he’s not! Who told you that?

YO: I’m just joking.

IR: And Omegas, we love y’all, too, even though your parties smell like ass and booty hos.

YO: But you see, they didn’t even come for us!

IR: They did not come for us.

YO: Omegas don’t watch the show!

With the season going back to the beginning of the show, I wanted to do that in this conversation. Issa, what are your memories of Yvonne getting cast at the very beginning of the show?

IR: I mean, I’ve been following Yvonne since like, 2008, just seeing her presence on social media. She was super funny to me, and I friended her on Facebook. Were you in D.C. at the time, or were you in New York?

YO: I went to Liberia after that, friend, and then I was in New York.

IR: And then she moved to L.A., and I had started doing Awkward Black Girl, and independent of me friending her on Facebook, she hit me to be like, “Oh, I love your show Awkward Black Girl,” and I was like “Bitch, I love you! We’re Facebook friends!”

YO: I was like, what?

IR: And I was like, “I’m having this party! Come on over!” And she came, which is sketchy on her part. I was a stranger.

YO: It was a wine down. And I was like, “This Issa Rae chick is really friendly! She just followed me on Twitter!”

IR: I had already decided we were friends, unbeknownst to you. And then there were these African fashion shows that were happening, and I had a friend I went to high school with who would ask me to come and sometimes host the red carpet. So I saw Yvonne hosting one of them, and I was like, “Man, she really reminds me of my best friend.” And then when the pilot got green-lit to shoot, I hit her and was like “Yo, this is happening, I would love for you to audition.” And at the same time, she had her show that she was promoting, First Gen, and I got to see that she can really do this and she wants to act in addition to being a comedian and a hilarious host. And 72 auditions later–

YO: 89 auditions later.

IR: She got the role.

YO: How many people did you see for Molly?

IR: We saw a lot of people for Molly. It was based off of someone, so for me, I had it in my mind, and Prentice [Penny] and Melina [Matsoukas] just with the page, were trying to find their version of who they thought Molly was. So we were seeing various different versions of actresses. And then you saw who you tested with, and they were all great, but there was just something about you, and our natural chemistry, because I wanted to be your friend, girl. So that’s what it was.

YO: Aw! “You’re my best friend …”

What was that memory from your side, Yvonne?

YO: Very similar. The first audition was good because I was new. And then I remember the note that Vicki Thomas, the casting director, gave for the second one. She called, and was like, “So, the producers have a note.” I was like, “Okay, great.” “Do less.” [Laughs.] I was like, “I’m sorry?” “Just, you know, do less.” I asked her to expound three more times, and she did not deviate from that note. She was like, “You know, the hands, and just the — do less.” So then I was like, “Cool, cool, cool, cool, cool.” Took a whole acting class to figure out how to do less. Then the fourth audition was the chemistry test with Issa and I, and that was the moment — because we were literally in chairs like this, and we were doing the scene from the pilot in the car when they get into an argument and she’s texting Daniel. And I walked out and I was like, “Yo, fam! I don’t know who they looking for, but if it’s not me, the show is whack!” I think that was the one time I was ever confident in this whole process! And then came the fifth and final test at HBO, and then I cried in my car because I was like, “It’s not me, it’s fine! I don’t even care! I’m gonna do my own show!”

Issa, was First Gen a part of what interested you in her for the part, or Yvonne, did you also make that with Awkward Black Girl in mind?

YO: No. Before I did that trailer, I watched every trailer that came out on ABC that year. This was like 2014 to 2015, so ABC was doing Black-ish, Fresh Off the Boat — whatever family show that was a comedy on ABC, I watched that and then created my trailer because I was like, “That is the home. I want to do a family show about immigrants from the continent.”

IR: And to answer your question, no. When I saw her onstage that day, that was already etched in my mind: “Oh, she reminds me of my best friend.” And then, “Oh, I’m writing this show based on her, let me hit her up and see what’s up.”

YO: And it was so funny because when we shot the pilot, Jerome, who’s here, we had this scene outside of a club, and he was like, “Wow, you are just like Megan!” And I was like, “I don’t know who this Megan chick is!” I had never met. And I was like, “Are you serious?” We were just standing outside, in front of the lowrider Cadillac, and I was like, Wow, all right, I guess when something’s for you, it’s for you, because I’ve never met her. And then when we actually did meet, it was like, “Hey, you got a booty like me! You can dance too!” So we had a moment. It was all body parts.

I was rewatching the first episode, and your first conversation is the broken pussy conversation. 

YO: [Sighs.]

Was that the first scene you shot together?

IR: No, the first thing we shot together was the car fight scene. The first day of the pilot was mostly Molly scenes because they wanted to give me a chance to ease into it, which I appreciated. And so it was all on you.

YO: Meanwhile, I thought I was going to get recast!

IR: No, it was perfect! I remember watching her do the scenes was just like “Ah, yes, we did it right! It’s perfect, she looks so beautiful, she’s so funny in this.” And then the last scene of the day, I was like, “Well, let me not fuck this up!” Shit, we did everything else right, and I was very nervous to be in that scene with her because it had been established that she was killing it all day, and up until that point, nobody had ever seen me be the role.

YO: Wait, no. After, like, 85 seasons of Awkward Black Girl, you were really still like–

IR: Two seasons.

YO: 85.

IR: And this is a TV show, this is not something I was editing in my fucking bedroom. It was like, Oh, there’s stakes here, and I can fuck my own shit up, and you’re doing a great job, so let me come in here and ruin it! But it ended up being so much fun and just established the dynamic.

YO: Perspective is so interesting because what I remember from that first day was Prentice giving me so many notes and me literally going home crying because I was like–

IR: That day?

YO: It was like, one of the first days.

IR: No, the Merkato day is when you cried. I remember. [Laughs.]

YO: I remember! He was giving me notes and I didn’t know how TV worked. This was my first time. Prentice was already in edit bay, and so he was like, “Hey, can we try this?” It was when Molly’s coming out of the car to go meet the League folks, so it was season one. And he was just like, “Hey, can you come up this way? Okay, now can you answer the call sad? Okay, can you take the call like you’re angry? Okay, can you …” and I was like, “Which one do you want?” I felt like I’m not doing a good job, so he keeps giving me other options because clearly I’m not doing the first one right. So I went home and had my own mirror moment when I was like, “Okay, you just have to be a thug about it. Have the conversation.” You know what I’m saying? Shoulders and everything. And I had the conversation, like, “Hey, Prentice, can I talk to you for a second?” And I did roll up on you the next day, like, “Hey, I just feel like I’m not giving you guys what you need, so can you let me know? I feel like I’m good at taking direction …”

And Prentice gives a look of like, “What the hell are you talking about?” He was so confused! And I was like, “Oh, because yesterday,” and he was like, “No, I just don’t want us to get stuck when we’re editing and we don’t have it. I just wanted to get options!” And I remember that was the first time I wanted to be like, “Can you lead with that, then? I need you to start the conversations with ‘You’re doing great! You’re gonna be a star!’”

Did you feel when you were making it, This is coming together?

IR: No, no. Not until the edit, and even the edit, seeing that first pilot cut was like, “Oh, it looks good, but is it good?” I was too close to it. We put it all on the table, we told the story we wanted to tell — are they gonna get it? Are they gonna recognize it? Just the typical nerves. But I didn’t know. I knew it looked better than I had imagined. I knew Melina had killed it. But I have imposter syndrome. I didn’t have full faith until the president emailed us that first night. He got the cut, and it was something super dry, like, “You’re onto something.” And I was like, “Yes! We did it! I know! Yeah, you see it!” [Laughs.]

YO: Do you remember calling me after the pilot got picked up? You were like, “Hey, girl! I just want to say thank you so much, our show’s getting picked up, thank you for doing this with me!” And I was like, “Doing this with you? What else was I gonna be doing?” It spoke to your graciousness in that moment, and it was also kind of like a little kid who got what she wanted for Christmas. It was so earnest and filled with so much joy, but then at the same time, like, “I want you guys to play with my toy.” I was like “Wow, she shares.” [Laughs.]

Did you always know that one of the central relationships would be Issa and Molly?

IR: Without a doubt. That’s what we came into it discussing. Prentice and I were always on the same page in terms of making sure their friendship felt real and that we weren’t setting out to make them frenemies or break up, but that they would be the core love story of the show. And I think we stayed true to that.

YO: I love you.

IR: I love you too, baby!

YO: I didn’t feel that!

IR: I love you.

YO: Okay, I felt that.

Because friendships are just as important as our romantic relationships, and they take work. They’re painful. You have to put in the time.

IR: You absolutely have to put in the time. I think friendships are taken for granted in so many ways, and they’re not given the same respect and care as romantic relationships. And especially friendship breakups. I mean, that’s one of the things we discussed in the room. So many of us — aside from the men in the room. I feel like men don’t have real friendships–

YO: They don’t. [Laughs.] Because they be with dudes they knew since eighth grade!

IR: Yeah, and be like, “Yeah, n- - - - -, I found my girl, but we still cool! We just don’t talk!”

YO: I hate ’em!

IR: “I’ll invite him, and he’ll be my best man, but I don’t speak to that n- - - - -.” But the women in the room, we all had examples of broken friendships we were bruised from. Some had spoken to therapists about it. We came to the realization that there’s not really a platform that has showcased the friendship breakup and the toll it takes on you. Because it hurts. It really, really fucking hurts.

How did your own relationship develop over the years doing the show?

IR: She’s become a sister to me in so many ways. She’s the type of person to just have your back, to look out for you. She’s one of the most considerate people I’ve ever met, so much so that I aspire to be that way. I just am not! And you’re always giving me advice. Even in other relationships and friendships, you’ll be like, “Just do this, just do this” and I’ll be like, “That didn’t even occur to me.” She’s such a genuine person, and I feel so blessed to have actually made a true friend during this process, even though I set her up to do that the whole time! It was all part of my plan. So I won.

YO: You don’t give yourself enough credit for how good of a human you are, which also translates to how good of a person and friend you are. Like, yes, I’m considerate, but I’m also like, ho, you changed my life! You don’t have to be more considerate than that! I can get your water. What I can’t get is my mama a house, but you did that! It’s not apples to apples. Because the reality is, Issa took a shot on so many people in season one. It was just her being like, “I want to make a show with people I think can do it.” And convincing the network that was acceptable. And now we’re all doing it in our own ways, but that’s because that’s your heart. So, sure, you’re not as considerate, waaaahhh … but like, you’re fine.

IR: Thank you, girl.

Was it hard convincing the network to do that in the beginning?

IR: The network came on board. Initially, they wanted experience. Having done this for several shows, they pitched directors who were bigger names, who were sexy. In their defense, they could put it on the trailer or the poster and be like, “It came from this person! You have to watch!” And then the more I met with people, the more it became clear that either they didn’t understand the show or it just wasn’t the right dynamic.

Who did you meet?

IR: I’m not gonna do that! But I will say, there was one big-name director who I’m a huge fan of. They were pushing him so much so that they were like, “He’s not from L.A., but we’ll send a jet every week for him to shoot the show.” And I was like, “Y’all gonna send a jet for him, and we all don’t have a budget to shoot this shit? Okay, cool, great.” So they flew me out to meet him, and it just wasn’t right, you know? As much of a fan as I was of his, I thought, We’re not gonna make the show that I want to make together. I was gonna tell him “Hey, this isn’t gonna work,” but he ended up backing out, and I was so relieved. And then I saw him at a party in season two when the show was out. [Laughs.] And he was like, “Yo! I saw your show!” And I was like, “Dope!” and he was like, “I woulda fucked that shit up!” It was so validating.

YO: It sounds just like him!

Vulture did a writers’ room talk for Insecure, and my understanding was that during season four, when it was real tense between your two characters, there was a tally: one for Molly, one for Issa. Yvonne, was the tally fair?

IR: Before the internet commentary, was the tally fair?

YO: So, we actually watched season four together.

IR: Before the internet commentary, but okay.

YO: See, this is the reason why there’s no longer a show. [Laughs.] No, we actually watched season four together, and we were keeping a tally, and Issa Dee was at, like, ten, and Molly was at, like, three.

IR: No.

YO: She was at, like, four.

Was it strikes?

YO: Ten strikes.

IR: Her and my real best friend were watching. We did a viewing of the past seasons in a theater, and I was between Yvonne and my real best friend as they were tallying, “Uh, that’s a strike for Issa! Huh, girl?” And I was like, “Y’all clearly biased!”

YO: And so okay, at the block party, I mean, Molly had one of those super-strikes. It was like, I was a ten and you were a ten and she was a four, and then I was like, “Cool, we both a ten.”

IR: The parking spot, though? The parking spot is honestly the only regret. That is what did it. That didn’t do Molly any favors — she tried to steal a parking spot from Issa, and the way that it was configured, I would have switched those roles.

YO: She’s just a bad driver. It’s not her fault. Issa–

IR: [To an audience member.] It was Issa’s spot, I agree.

YO: I’m sorry, I didn’t know this was a call and response! Are we in church? I’m sorry, is there an offering plate being passed around? What’s going on? The problem is [Laughs.] when we were shooting season four, I don’t think anybody knew. I was so oblivious: “Oh, these are some good scripts. Yeah, girl, friendships do be like that. I just felt like we were just acting!

IR: And for us as writers, we were accumulating the entire show. If you look at season one, Issa is a terrible fucking friend! She really is. And so I think, overall, if you look at the series from one to four, it is even, but I think the nature of watching television, you’re rooting for the protagonist.

YO: I’m sorry, I don’t remember any interviews of you saying–

IR: Because you had to be in the interviews. They cut those parts out.

YO: I read all of them. I have Google Alerts on you. This is the first time I have heard you say–

IR: But it’s true, it’s true.

YO: Okay, now it’s true. Where were you last season when I needed you?

IR: Doing interviews!

YO: [Singing.] Haters, they gon’ hate. Ballers, they gon’ ball.

Did the fan response surprise you during season four?

YO: I think it surprised me.

IR: She was very hurt, guys.

YO: I’m still hurt, okay?

IR: We planned as writers to build it out over four episodes, back and forth, back and forth. “This is Issa’s infraction, this is Molly’s.” And episode one, people were like, “Oh, Molly is a motherfucking bitch! Did y’all hear that shit?” We were like, “Oh, they’re catching on to what we’re doing already! That’s crazy, but they’re going at it a little hard. But we’re gonna get ’em back.” Episode two, they gonna see what Issa does–

YO: And I was looking forward to it! I put the meme out, like, “Ha! Wait till next week!” And next week they were like, “Nah!”

IR: And then as it progressed, we’d talk, and she’d be like, “They’re all up on Molly! Do they see what Issa is doing? What’s the problem?”

YO: Listen, growing up, I was the snitch in the family, right? So watching it, I was like, did the audience not see when Molly was there in season one when Daniel came to the thing? And I was like, “Wow!” These fans ain’t loyal.

I mean, it was a challenging season in my life. But what it really was like was, “Is it about to affect my money?” because my special was coming out. And folks was like, “Nah, they’re trying to throw the set! We’re not gonna watch this trash!” I was like, “Wait a damn minute!” So … it’s fine. We got through it.

Shooting the fight scenes, like the block party, was that hard? 

IR: That season was really hard because some of our favorite scenes are like, “I get to work with Yvonne today. I know it’s gonna be jokes all day.” And it is. Like, like the block party was fun to shoot. But there was still this looming tension of Ugh, we gotta do this fight scene. And I think we did the fight scene last on a day. The first day was us being cool, so it was okay. But to do an overnight shoot and also to be like, you were in a different emotional space because you were the one most affected. You were the one who wanted to come at Issa.

But I also think about, like, season one, episode seven. That was one of our first fight scenes, and that was weird to do. Prentice had to tell us, “Y’all can’t crack jokes in between. Stay there! Stay there!”

YO: We didn’t want to stay in character season one! I was like, “It’s your fault because you — girl, you want to go crash after this? You need a snack?”

IR: “You good? You good?” But yeah, by episode five I think, in season four, we really felt that tension.

YO: For me, they’re really hard, because Issa is lovable. She is just love personified. I remember season one, you were like, “I wrote this. I don’t really want to be saying these things to you.” And then season four was hard because we weren’t shooting together at all, like, the whole season. And then the one day where I’m like, “Hey, girl, I miss you!” she was like, “Oh, I gotta hate you. Here we go.” That was very difficult. I remember after season one, I went home and watched Veep for two hours just to calm down because I was still mad! It was also the first time we had shot a very angry scene, and I was like, “This is triggering. It’s eighth grade all over again. I hate you Taisha.” Nah, I’m just joking — wherever you are! [Laughs.] Please, strike that name from the record!

Issa Rae and Yvonne Orji on 5 Years of Issa and Molly