< Issa Rae on the belief that gets her through 'stupid mistakes and bad decisions'

RACHEL MARTIN, HOST:

Hey, it's Rachel. Just a heads-up - this episode contains some expertly deployed swearing.

Do you have a belief system that helps you make sense of the world?

ISSA RAE: Yes, that everything happens for a reason.

(SOUNDBITE OF MUSIC)

RAE: That gets me through so much that that gets me through those stupid mistakes and bad decisions.

MARTIN: Hey, I'm Rachel Martin, and this is WILD CARD, the game where cards control the conversation. Each week, my guest chooses questions at random...

Three cards in my hand - you pick a card one through three.

RAE: Three.

MARTIN: Three.

...Questions about the memories, insights and beliefs that have shaped their lives. This week, comedian, writer, producer and actor Issa Rae is playing the game.

RAE: Oh, my God, if that hadn't happened, I wouldn't have had the happiness that I have today.

MARTIN: So I came away from a conversation with Issa Rae, and it was clear to me that she's genuinely happy and secure in who she is at this stage of the game, which is notable, considering her breakout hit was a show on HBO called "Insecure." The show was based a lot on her own experiences as a young single Black woman making her way through life in LA.

And Issa Rae does have a lot to feel good about right now. She was in three Oscar-nominated films in 2023, including "American Fiction" and "Barbie," where she was cast as president of Barbie World. But Issa's amazing career is about way more than just acting. She's basically a one-woman media empire promoting and investing in people of color, and she's doing it not just in the movies but also in music and business. Issa Rae clearly has big plans. She also has this vibe and this smile and this external confidence that makes me believe she's going to do it all.

Issa Rae, I am so happy that you're here. Thank you for doing this.

RAE: I'm so happy to be here.

MARTIN: So your projects are infused with, like, this very positive energy.

RAE: Well, thank you.

MARTIN: So it seems like you're walking through the world in a pretty good light.

RAE: I have always been optimistic, and I think there's a little bit of delusion behind that, and I think I've kept that delusion 'cause you have to be a little bit delusional to, like, dream and think you can...

MARTIN: Yeah.

RAE: ...Achieve dreams. And I think the contrary would make me sad, and I don't like to live in sad places. And I always also see the best in people until I don't.

MARTIN: Yeah, yeah. So you got a lot going on besides acting. I read that you're partnering with HBO again on your own project that you're writing and creating.

RAE: Yeah, I'm in a deal with them. They're my favorite collaborators. I'm really excited about - I'm excited about so much. It feels different than anything that I've done before while still tackling things that deeply scare me. And I love to write from a place of fear.

MARTIN: Whoa. Why?

RAE: Because pre-therapy me, that was the only way to acknowledge what I was scared of and work through it and add humor to it, which I'm - want to do always, just to help, yeah, get through it in so many ways. And also, even in making something, you get to invite other people into your fears. And anytime someone else is involved in a scary situation with you, it becomes less scary. It's just a great way to work through it.

MARTIN: OK, I feel like there's a lot untapped there that we didn't get to, but maybe the game will bring it up for us.

RAE: Yes, let's get it.

MARTIN: So here's the game. In front of me, there's a deck of cards. It's real. On each of these cards is a question that I would love for you to answer, and you are going to randomly choose which ones that I ask.

RAE: OK.

MARTIN: There are two rules, OK? You get one skip. If you use your skip, then I'll just replace it with another one in the deck, in the same deck. And you get one flip. So this is when you can put me on the spot, and I'll answer it before you do. You've still got to answer it...

RAE: Oh, you...

MARTIN: ...But I can...

RAE: OK. OK. All right, all right.

MARTIN: We are breaking it up into rounds, OK? So the first one is memories. The next one is insights or lessons that you're learning right now. And the last one is beliefs, how you see the world.

RAE: OK.

MARTIN: And since this is a game, I know you're going to be into the fact that there is a prize at the end.

RAE: Oh, yes. Oh.

MARTIN: Yes, there is.

RAE: Come on. Make the game worth playing. I know that's - yes, I'm into it now.

MARTIN: OK, good. So Round 1 - memories. Here we go. There are three cards in my hand. You pick a card one through three - one, two, three.

RAE: Three.

MARTIN: Three. What's a moment when you felt proud of yourself as a kid?

RAE: A moment when I felt proud of myself was definitely making my older brothers laugh. My entire family is funny, but my older brothers, in particular, are so funny to me, and they are closer in age. So they have a rapport. And I was the third sibling, the middle child ultimately that came six years later. So while they're two years apart, me and my older brother...

MARTIN: Yeah.

RAE: ...Are six years apart. So I was always like, the girl, the...

MARTIN: Yeah.

RAE: ...Young one. And so making them laugh was, like, am I part of the club now?

MARTIN: Were you?

RAE: And I wasn't.

MARTIN: OK (laughter).

RAE: It was very short-lived because then it was like I tried too hard to continue it, you know?

MARTIN: Yeah.

RAE: You can't...

MARTIN: Yeah.

RAE: ...They - nobody likes a try-hard.

MARTIN: No, which is really difficult when you're a kid who wants to be...

RAE: Yeah.

MARTIN: ...Accepted by your older brothers. Did you have a particular brand of comedy at that age? Was it physical comedy? Was it puns, knock-knock jokes?

RAE: Oh, what a good question.

MARTIN: Well, thank you, Issa.

RAE: It was (laughter) probably - there was a physical element, yeah, because it it was rooted in imitation. And then storytelling - I like to tell stories, you know, things that happened. And I think inevitably that turned into then my commentary on things that happened.

MARTIN: And you still sort of do that.

RAE: I do. Look at that.

MARTIN: OK. So we are going to the next question here. Pick a card - one, two, three.

RAE: One.

MARTIN: One - when was a time in your childhood when you realized the adults in your life didn't have all the answers?

RAE: Didn't have all the answers. I mean, the first thing that comes to mind, which I'm like, ugh, is probably when my parents got divorced. And I was like, what? Because I didn't see it coming, and I was like, y'all can't figure this out? What's going on? What happened? Because they also, initially - which, they blamed it on cultural differences. My dad is Senegalese. My mom is American, and I was like, that's dumb. You guys know each other's culture.

MARTIN: Is that what they told you? That was the messaging?

RAE: Yes. That's what they told the last three of us, the younger siblings. But I was in high school. So I was like, smart enough to know clearly not, but smart enough to know there was more to it. But to me, I just remember thinking, like, they - this is something that can and should be fixed and they just don't know what they're doing.

MARTIN: But did it - because you were older, did you have a pretty good sense of feeling secure in your own life or did it unmoor you to some degree?

RAE: It unmoored me. What do you mean? Yes. I think to this day. I mean, it colors relationships. It colors the way that you - it colors your perception of so much because, I mean, again, I didn't see this coming, so I was like, what else don't I see coming? What else don't I know? And what else have I translated wrong in my world view? So yeah, that's stuff that I'm still deciphering and like, we're all - everybody's fine now. You know, we're on a big family group chat. There's too many messages that come through.

MARTIN: With your dad?

RAE: Yes, with my dad. He sent, like eight videos back to back yesterday.

(LAUGHTER)

RAE: But it was just kind of unnerving. And for, like, I love to write about relationships, and I'm obsessed with relationships I think because of that.

MARTIN: We've got to take a quick break, but we'll be back with Round 2 with Issa Rae.

RAE: And I was talking to my friend about this, actually, just this weekend. I don't know why we were just casually talking about death on the way to a winery.

(SOUNDBITE OF MUSIC)

MARTIN: We're moving on. That was round one. Round two.

RAE: All right.

MARTIN: Insights - stuff you're working on.

RAE: I can do this.

MARTIN: Yeah, you can. OK. We got three more cards. One, two, three - pick a card.

RAE: Two.

MARTIN: Two. Oh, how comfortable are you with silence?

RAE: Generally? I love silence. Though...

MARTIN: You do?

RAE: ...Though, my - yeah, I like to be alone a lot of places.

MARTIN: Do you need that?

RAE: Yes.

MARTIN: Like, I need - I need - I, like, actually need to get away from people and not talk, but you seem like an extroverted human being who might...

RAE: Are you insane?

MARTIN: (Laughter).

RAE: Thank you for that. I am not. I am extraverted around around my own confines. I have to curate...

MARTIN: Yeah.

RAE: ...The ability to be an extravert. But no, generally, I love being alone. I like traveling alone. I like eating alone. I love going to the movies alone sometimes. And I still love the people I love, but it's necessary.

MARTIN: Yeah.

RAE: Though I will say, my friend talked about - she's going on a silent retreat. And I was like...

MARTIN: Yeah,.

RAE: ...Oh, what is that? And she was like, you can't have your device. You can't read. You can't...

MARTIN: Yeah.

RAE: And that is terrifying to me. I'm just like, that's terrifyingly boring because I like my silence doing things and, you know, it is about being alone with your thoughts and seeing what comes out of it. But yeah, I don't know that I could do that. I could, because I can do anything competitively.

MARTIN: Of course you can. Right? I would win that silent retreat so hard.

RAE: Yeah. I would shut the f*** up so f***ing hard. Excuse my cursing, by the way. I'm sorry. I will be better. I know this is NPR.

MARTIN: You know, it's my New Year's resolution all the time. And then I tell my kids that swearing's lazy, and I try to come up with different words, and then I can't.

RAE: (Laughter).

MARTIN: So it's OK. OK. OK. Let's move. Let's move to the next set of cards. (Vocalizing). We're still in insights, in case you're playing along at home. One, two, three.

RAE: Three.

MARTIN: What's a failure you still think about?

RAE: A failure I still think about. I'm going to do one of those annoying things and say I don't believe in failure unless you stop. But they're - can I translate...

MARTIN: I want to let you explain...

RAE: ...That?

MARTIN: ...That. I believe that's a real thing.

RAE: Yeah. I'm, like, I don't fail anything unless I say I'm not going to do this anymore, so - oh, OK. I mean, in that case, a failure I think about is there's a failure of education. And I will say that - and I'm thinking about my dad, but, like, I didn't take being in college seriously in that way. And, like, he wanted me to pursue, like, my higher degree and all these other things, and I know that would've made him proud, but I had no interest in it at the time. And then I was, like - I stepped back and I was like, I really just wasted resources in ways. And, yes, my life went on a different path, and I pursued passions. But there's so many things there where I'm just like, I didn't wholly take advantage of the opportunity. And I feel like I failed at that period of my life.

MARTIN: But can you explain to me that whole idea that you don't believe in failure, really? Like, I get...

RAE: Yeah.

MARTIN: ...It for sure. But there - is it just the label that bugs you? Because there are definitely things I have not succeeded at. And it doesn't - it's not - it doesn't haunt me, but I still recognize them as failures, and it's OK. But maybe that word itself carries a lot of baggage or feels pejorative?

RAE: Yeah, I guess because I associate failure with a test. It just feels like a - it feels like the end, and I don't know that I've reached the end of anything that matters to me where I would consider it...

MARTIN: Yeah.

RAE: ...Failures. Like, I'm like, I'm still going. I still have a chance to succeed. I think I've made stupid decisions, bad mistakes and, like, those kind of things, but I can't say that I've failed anything but, like, tests or, like, actual things that were constructed to either pass or fail. If - and so I guess that's my thing.

MARTIN: No, I think that makes sense. And I think it makes sense for people who are highly successful. I think they're...

RAE: (Laughter).

MARTIN: Sorry, but it does. Like, you've had a lot of success. It makes sense that you can't really frame things in your life as failures because then you stop, like, putting yourself out there and taking risks.

RAE: But other people can easily. I'm sure somebody's listening to this - b****, I know you failed. I think it's all perception. Some collaborators may be like, you failed me. But I think, yes, again, it's just in the way that you see things. But I'm like, in my mind, I'm still trying.

(SOUNDBITE OF MUSIC)

MARTIN: OK. Three more cards. Last one in this round. One, two, three.

RAE: One.

MARTIN: One. What are you afraid of at this point in your life?

RAE: Infinity. Eternity. Eternity scares me to no end. There's no end. Like, OK, yeah, you die - fine. I can wrap my head around that. But then what is forever? What is that? It just keeps on going?

MARTIN: Yeah, it keeps on going.

RAE: And I was talking to my friend about this, actually. We were - just this weekend. I don't know why. We were just casually talking about death on the way to a winery.

MARTIN: That's my kind of conversation.

RAE: (Laughter) Yeah, high key.

MARTIN: For real.

RAE: You're the perfect person to talk to. He was like, I just have come to terms with the fact that once you die, you're just gone. And I was like, what about the forever of it? And he was like, I haven't really thought about that. I just think that's, like, human - humanity's ego. There's nothing after in the afterlife. You're just done. And I have never heard anyone I love say that. And I started spinning out where I was just like, he - this person I love is talking about dying and has just accepted the fact that it's done. There's no reincarnation for him 'cause even that is still scary. There's still, like, I'm just going to appear as either another person or an object or an insect or whatever it is. But, like - it doesn't stop. There's no concept of the ending. So that is a fear of mine.

MARTIN: Like, is that the thing you think about at 3 o'clock in the morning, the infiniteness of the universe?

RAE: I feel like all of life's distractions free me from thinking. There's a period where if I let my - like so many of us, where if I let my mind wander for too long, it inevitably goes there. And there's that - I can't think past this because I can't wrap my head around it or comprehend it. And then when I'm high, (laughter) that occurs.

MARTIN: Yes.

RAE: That is...

MARTIN: Yes.

RAE: ...Also, like, some of the worst trips.

(SOUNDBITE OF MUSIC)

MARTIN: All right. We've got to take another break. Then we are back for the final round with Issa Rae.

RAE: If this thing that I really wanted didn't come to me, it was because it was supposed to go to this person. And they're having a great time. I'm so happy for them. Like, it just wasn't for me.

(SOUNDBITE OF MUSIC)

MARTIN: OK, this is Round 3. This is, like, big-picture, like, belief stuff. These are three cards.

RAE: I'm going to go the middle this time.

MARTIN: One, two, three. Middle. Two. I feel like you like the two.

RAE: I do.

MARTIN: Do you have a belief system that helps you make sense of the world?

RAE: Yes, that everything happens for a reason. That gets me through so much. That gets me through those stupid mistakes and bad decisions. I'm a big fork-in-the-road person. That is also something that haunts me. And that's a fear that is past the infinity of it all or the eternity of it all, is just, like, going down the wrong path. And so I assuage those concerns and fears by saying, like, this all happens for a reason. The reason could be - could benefit me, or it'll benefit someone else. If this thing that I really wanted didn't come to me. It was because it was supposed to go to this person. And they're having a great time. I'm so happy for them. Like, it just wasn't for me.

MARTIN: (Laughter) Can you give me an example of the fork in the road? Is there a really profound one that you still think about?

RAE: Yeah.

MARTIN: The other life?

RAE: The Paris trip - the studying abroad overseas. There was - I was supposed to study abroad. I was supposed to go to Paris, and there was also, like, a guy there that I was talking to really seriously. But I had this opportunity to submit -what was it? Oh, it was, like, a Sundance thing and - for a script that I'd written with a friend. But I had to be in town if we won. And we were semi finalists, and so, If I went to Paris, I just wouldn't be able to get the opportunity to, like, do this Sundance thing. And so, you know, it was going to be lit. All my friends were studying abroad in Paris. This guy was there, and he was like, one of my first real loves, and that would have been - it would have just been a different life path. And we weren't finalists. So I had wasted this trip and the memories and the chance that whatever that would have been, in...

MARTIN: That relationship?

RAE: Yes. And then was just back at school. But I always wonder, like, what would my life have been? How many children would I have prematurely if I had taken that trip? But there are so many other moments where it's just, oh, my God, if that hadn't happened, I wouldn't have had the happiness that I have today. There are a couple things like that that sometimes keep me up at night.

MARTIN: Yeah. You don't need me to tell you, but you weren't supposed to be with that guy. Or - do you know where he is?

RAE: Definitely wasn't supposed to be with that guy at all, at all. But I still think about it.

MARTIN: Yeah. I think that's natural. You thinking about it right now?

RAE: (Laughter) Shoot, that wasn't supposed to be, all right? That wasn't supposed to be seen. I'm happily married.

MARTIN: OK. So we are, yeah, we're in belief still. One, two, three - three new cards.

RAE: Three. I feel like anybody's listening is like, just choose three. You haven't chosen three.

MARTIN: Oh. Let's see how this goes. How do you stay connected to people you've lost?

RAE: Thinking about them constantly because thinking about them keeps them alive forever. Sometimes talking to them. And with one particular person, a family member, we have - my mom and I and now the entire family have determined that, like, whenever we see a hummingbird, there's - that person is - they are thinking of us. And it always aligns at the perfect times, honestly. Any time where I feel like I need her or she's missing something that I know that she would've just been ecstatic to see or just needed to be there for, that hummingbird will be there, either for me or for my mom or for my brother or whatever the case is. So whatever that is, whether it's true or not, it's real to us, and I think that's also a way of just preserving their memory because it's hard. It's hard to accept that these people that we love and who we feel are supposed to be here with us aren't. And so we find ways to make sure that they are. And I think I'm good about that and intentional about that.

MARTIN: I do that, too. Seagulls - isn't that weird? My mom really liked them.

RAE: Seagulls?

MARTIN: And I was like, they're, like, garbage eaters, but she loved them. And it's so random. But they come up to me, same. Like, one will be where it's not supposed - I'm like, there's no ocean around here. What are you doing?

RAE: Yes.

MARTIN: You're lost, little seagull.

RAE: That's beautiful.

MARTIN: Why are you in Washington, D.C.?

RAE: Why are you eating garbage in Washington, D.C.?

MARTIN: Right.

(LAUGHTER).

MARTIN: OK. Last one. Last one. One, two, three.

RAE: Let's go three again. Living it up.

MARTIN: I love this one, and I'm so glad it came up. Has your idea of what it means to be a good person changed?

RAE: Wow. Yes and no. Yeah, over time it's just been about, I think, empathy and consideration. That's what it's evolved into. Before it was like, just be kind. That's the younger version of me. Treat people how you want to be treated.

MARTIN: Yeah.

RAE: Be kind. But I think there's just - there's more to it than that, and that's what's evolved. It's also showing up in a real way. But I think the core - I still think nothing makes me feel better than an act of kindness from somebody random.

MARTIN: Yeah.

RAE: That just warms my spirit. And it could be something as small as someone holding an elevator open, and you saying thank you, them being like, you're so welcome - have a great day. Like, something like that, I'll think about that for hours and just be like...

MARTIN: Totally.

RAE: They did not even have to do that, and they meant that. And that's - those moments of just connection and people just seeing you and considering you, that makes me feel special. And I think it goes a long way. It's such a reminder that people want to be good, and we need those reminders so much.

MARTIN: Yeah. I do, too. Like, I get weepy sometimes. My husband's like, what are you talking about, person held the door for you (laughter)?

RAE: No, same.

MARTIN: I know, they did.

(SOUNDBITE OF MUSIC)

RAE: (Laughter) They did it - it was the way they did it. You had to be there.

MARTIN: Or, like, the parking attendant was just really - like when he asked how I was doing today.

RAE: Yep.

MARTIN: You could tell that he really meant it.

RAE: Yep, yep.

MARTIN: Thank you. Thank you so much.

RAE: I needed you to ask me that and you have no idea. Yep.

MARTIN: Yes.

RAE: That's literally it, is seeing each other.

(SOUNDBITE OF MUSIC)

MARTIN: You won, Issa.

RAE: Yes, because I didn't skip, right? That's why I won.

MARTIN: That's right. Boom.

RAE: (Laughter).

MARTIN: Oh, my God. You're hilarious.

(LAUGHTER)

MARTIN: You get a prize. It's a trip in our memory time machine (mimicking time machine).

RAE: (Laughter).

MARTIN: You're like, I thought I was done, Rachel. I gave you all my special moments. No. No, Issa Rae. No, you're not done. We're taking a trip in the memory time machine to one moment in your life where you wouldn't change anything about it, not one thing, but you would just like to hang out there a little bit longer.

RAE: Oh. Thanksgiving after the food is done, hanging around the kitchen, all five of us. Five siblings, mom, memories, laughs, playing this game, the Don't Laugh and Smile Game. My mom invented this game to keep us at the dinner table and not watch TV. And it was called the Don't Laugh and Smile Game. And it was basically, we all spent the dinner trying to make each other laugh. Whoever laughs first is out, so it's all of us trying to hold our laughter in.

MARTIN: (Laughter).

RAE: And so it just involves literally that, trying to make each other laugh, bringing up old memories, things that, you know, were embarrassing for someone else. It's just - in some cases, a roasting. But it's just...

MARTIN: Yeah.

RAE: I could hang out at that table forever because it's just bonding and the love we have for each other. And I don't know. I just - to go back to your fear, knowing that this will end, like, my grandmother just passed. And her brother now, my great uncle, is the last one out of all his siblings. And to see him, you know, sob at the funeral - and he's, like, the funny guy. But to see - and he's the youngest. And I started thinking about, oh, my God, this is gonna happen. I told my brother and sister, I was like, this is gonna be us one day. We'll - I've never thought about, like, losing you guys. And so, take me to that table. I can stay there for a long time. I can be reincarnated to that table.

MARTIN: Forever feels OK at that table?

RAE: It sure does (laughter). That was a nice prize. Thank you for that.

MARTIN: Good. Thank you for that. Issa Rae, it's been such a pleasure. Thank you so much, lady.

RAE: Likewise. Thank you. You're the game master now.

(SOUNDBITE OF MUSIC)

MARTIN: Next week on WILD CARD, we hear from actor and first-time director Chris Pine. He tells me why making his new movie helped him give up on seeking perfection.

CHRIS PINE: I had joy. I experienced joy. It still gives me joy. That's it. That's enough. There is no perfect - that is perfect.

(SOUNDBITE OF MUSIC)

MARTIN: Today's episode was produced by Cher Vincent and Lee Hale and edited by Dave Blanchard, with help from Lauren Gonzalez. It was fact-checked by Mary Glendinning and mastered by Gilly Moon. WILD CARD's executive producer is Beth Donovan. Our theme music is by Ramtin Arablouei. And in case you want to reach out to us, our email is [email protected]. We're going to shuffle the deck and be back with more next week. See you then.

(SOUNDBITE OF MUSIC)

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