Making Rihanna - An image of a young Rihanna (v2)
Photo courtesy of SRP Music Group
Making Rihanna - An image of a young Rihanna (v2)
Photo courtesy of SRP Music Group

Robyn Rihanna Fenty was just 16 when she signed a record deal with Jay-Z. She was 19 when her smash hit “Umbrella” took the world by storm. Now at 34, she is not only known as a popstar but also a fashion mogul and billionaire.

But how did she get here? On this week’s episode of Making, host Brandon Pope explores Rihanna’s origin story with music journalist Bill Werde, editor Chioma Nnadi and record producer Evan Rogers, who discovered Rihanna in Barbados in 2003.

“I warned her it’s a roller coaster, you’re gonna get kicked in the gut. Are you sure?” Rogers recalls asking the then-15-year old. “And I’ll never forget, with no hesitation it was like, ‘It’s all I’ve ever wanted.’”

Featuring exclusive archival tape of Rihanna’s early rehearsals, learn how Rihanna became a global icon.

This season of Making covers a different, iconic figure every week. Subscribe and don’t miss an episode.

Making Rihanna - An image of a young Rihanna (v2)
Photo courtesy of SRP Music Group
Making Rihanna - An image of a young Rihanna (v2)
Photo courtesy of SRP Music Group

Robyn Rihanna Fenty was just 16 when she signed a record deal with Jay-Z. She was 19 when her smash hit “Umbrella” took the world by storm. Now at 34, she is not only known as a popstar but also a fashion mogul and billionaire.

But how did she get here? On this week’s episode of Making, host Brandon Pope explores Rihanna’s origin story with music journalist Bill Werde, editor Chioma Nnadi and record producer Evan Rogers, who discovered Rihanna in Barbados in 2003.

“I warned her it’s a roller coaster, you’re gonna get kicked in the gut. Are you sure?” Rogers recalls asking the then-15-year old. “And I’ll never forget, with no hesitation it was like, ‘It’s all I’ve ever wanted.’”

Featuring exclusive archival tape of Rihanna’s early rehearsals, learn how Rihanna became a global icon.

This season of Making covers a different, iconic figure every week. Subscribe and don’t miss an episode.

S&M: Na na na, come on! 

Brandon Pope: International pop icon. 

S&M: Na na na, come on! 

Brandon Pope: Youngest self-made billionaire woman. 

S&M: Na na na, come on! 

Brandon Pope: And, fashion mogul 

S&M: Na na na, come on! Come on, come on. Na na na. 

ARCHIVE: What’s her name, Rihanna! 

ARCHIVE: Rihanna! 

ARCHIVE Kevin Hart: Rihanna! 

Brandon Pope: From WBEZ Chicago, this is Making. I'm Brandon Pope. Making is about the pivotal moments from an icon's life that skyrocketed them to greatness. Today, it’s Making Rihanna. She was just 16 when she signed a deal with Jay-Z. And 19 when her smash hit Umbrella took the world by storm. 

ARCHIVE TAYLOR SWIFT: And the Grammy goes to Rihanna ft. Jay-Z for Umbrella! 

Brandon Pope: But her legacy does not stop there. Now, she is changing the fashion industry as we know it. 

ARCHIVE: Bad girl RiRi is now rich girl RiRi. 

ARCHIVE: 34 years old and already a mogul recently gracing Forbes annual list. 

ARCHIVE: Making her the wealthiest female musician in the world and second to Oprah as richest entertainer. 

Brandon Pope: What takes someone from island girl with a catchy single, to a music and fashion supernova? 

ARCHIVE RIHANNA: You be fearless every day and when you do not feel like it, just pretend, girl. Really and truly don’t let them see you sweat. 

Brandon Pope: What were the years that defined bad girl Robyn Rihanna Fenty? Helping us answer that question is music journalist Bill Werde, editor Chioma Nnadi, and the record producer who discovered Rihanna, Evan Rogers. 

Evan Rogers: And I warned her it's a roller coaster, you're gonna get kicked in the gut. Are you sure? And I'll never forget with no hesitation. It was like it's all I've ever wanted. And I was like, that's the right answer. 

Brandon Pope: That’s today, on Making. 


ARCHIVE HERO: And then a hero comes along, with the strength to carry on… 

Brandon Pope: This is the voice of Robyn Rihanna Fenty age 15. Persuaded by her friends to sign up for her high school beauty pageant and talent show on her island home of Barbados. 

ARCHIVE RIHANNA: I dreamed of it though, I always dreamed of it, and I wanted to do it so bad. I always said by the time I’m 18 I want to be a singer, if not forget it. Yeah, because after you get 18 it’s kind of harder, and I had a back-up plan, psychology. 

Brandon Pope: Luckily, fame found her early on. In high school, she formed a trio with friends and performed Destiny’s Child songs. It wasn’t long before American record producer Evan Rogers visited Barbados with his wife, and the trio auditioned for him. She had the X factor. He recommended she go by her middle name, and she flew to the U.S. to record a demo. 

ARCHIVE PON DE REPLAY: Ooh, come, Mr. DJ, song pon de replay. Come, Mr. DJ, won't you turn the music up... 

Brandon Pope: Soon, she was in the room with the president and CEO of Def Jam Records, Jay-Z. 

ARCHIVE JAY-Z 2005: She has this outrageous song called “Pon de Replay.” And he played that song for me and I was scared I was like, that song is too big for her. And when she walked in our office, I was like, you know, she just had it. It was just something about her. 

ARCHIVE RIHANNA: I’ve never met a celebrity. And to have to audition for one and meet him at the same time, like Jay-Z, someone like him, I was so... I was hysterical.

ARCHIVE JAY-Z: We signed her that night, we didn’t let her leave the office. Really? Until 3 in the morning, was when that contract got signed. 

ARCHIVE RIHANNA: It was the longest 12 hours of my life. Like I was just waiting downstairs. And I was like, get the contract down here, I want to sign it, I want to sign it. I was so hype. I mean... But I was just looking at the roof like, oh gosh, is this happening? 

Brandon Pope: So Evan Rogers, I want to start with you. You were an executive at SRP Records in the early 2000s. Put us in the room with you, tell us the story of first seeing Rihanna perform in Barbados. She was just 15 years old. Right? So why were you there? And how did you discover her? 

Evan Rogers: So, okay, well, I was there because my wife is from Barbados. And so we would go to Barbados all the time. That's that's our.... Our main hang. Being a record producer, songwriter, people knew on the island, the word gets around. So it wasn't unusual for people to ask for auditions or, you know, so and so knows someone who can sing. So this was just another one of those. Three 15-year-old girls, could they come by the villa. And of course, you never know. And so the three of them came for their audition. Rihanna was late, went home, I believe to change, to get her look just how she wanted it. And they all sang for me, Rihanna sang "Dangerously in Love." And, I just heard something really unique and special in her vocals, even though they were raw. And she had a presence when she walked into the room. And it was just one of those moments, where I think I have something really special here. So I had to organize a follow up meeting with just her and her mother the next day. And that's when we had the talk about, do you want to come up and take a shot at this? And I warned her it's going to be a lot of... It's a roller coaster, you're gonna get kicked in the gut. It's like, the music business is tough. Are you sure? And I'll never forget with no hesitation, it was like. it's all I've ever wanted. And I was like, that's the right answer. 

Brandon Pope: All right, so after that you decided this is talent. I've got to nurture support, and you brought her all the way to the US. Take us from that moment with what happened all the way to "Pon de Replay."

Evan Rogers: It was right almost exactly a year from the time that I first met her that Veda Nobles played us this beat and this track for "Pon de Replay" and a girl named Majesty had written the lyrics. And we just knew this is... This is that door opener. This is that one, and I played it for her over the phone. And she was like, it sounds like a nursery rhyme, but I trust you guys. And then she came up, and when she put her voice on it, it was magic. 

Brandon Pope: That's the catchiest nursery rhyme I've ever heard. There's no doubt about that. 

Evan Rogers: Some of the biggest hits are like nursery rhymes. 

Brandon Pope: So, "Pon de Replay" happened. She hears it. Jay-Z gets a hold of it. L.A. Reid. What was their response to this? Evan Rogers We'd sent music and a few photographs to labels. And, Jay Brown had called us from Def Jam, and he was like, we gotta meet with her. The first label meeting was rough – didn't go well. It was like, whoa, this is going to be a little harder than we thought. Second meeting was Def Jam. You know, L.A. Reid walked in. And you could just feel the excitement from everybody. Tata, J. Brown, Jay-Z. Tracy Waples, the whole team there. Carl Sterk and my partner and I played acoustic guitar, and she sang "For the Love of You." 


Evan Rogers: And then she did "Pon de Replay." And she danced. She had choreography that it was like, oh, my God. It was so so crazy. But you just... They wouldn't let us leave. They're like, what do we got to do to cancel the rest of your meetings. And like she said, we were there until three in the morning.

Brandon Pope: Now, what you’re hearing is never-before-heard footage of Rihanna rehearsing with Evan. 


Brandon Pope: Now, Bill Werde, I want to bring you in here. Today, you’re the Director of the Bandier music business program at Syracuse University. Back then, you were the Editorial Director of Billboard during Riri’s S.O.S. days. So, what did you think of this young Dancehall artist at the time? 

Bill Werde: Yeah, I mean. It was really hard to anticipate that this was going to turn into one of those, you know, shortlist of like five or six biggest artists in the world. "Pond de Replay" was, you know, a cute song by an adorable newcomer to the, to the charts. But I don't know that, if I'm being honest, I would have said in that moment, oh, man, this is you know, this is gonna be a one name icon in a matter of time. 

Brandon Pope: All right, so if that wasn't the moment, then what was the moment where you said, okay, this this artists, Rihanna, she's got something here. She could be an icon. 

Bill Werde: Well, certainly "Umbrella" was the first time that the conversation shifted from this is a singer who has great singles to this as an artist who may be bigger than her songs. This is an artist with that identity. 


Brandon Pope: That voice doesn’t exactly sound like Rihanna, now does it? The man on the vocals is Terius Youngdell Nash, also known as The Dream. He wrote Umbrella with Tricky Stewart, and this is the demo. 

ARCHIVE DEMO: Trick starts to play this chord, and I kind of walk in at that same moment and I hear it. I said okay cool, turn the mic on, I maybe had to change four words, but I sung it from the top to the end, exactly as is how you hear the song today. 

Brandon Pope: They brought the song to Britney Spears. She said no. Then Mary J. Blige. She said no. Then, it found its way to 19-year-old Rihanna, and she killed it. 

ARCHIVE UMBRELLA: Because, when the sun shines, we’ll shine together, told you I’ll be here forever, said I’ll always be your friend, took an oath. Imma stick it out till the end. 

Brandon Pope: The song blew up. It topped the charts across the world. It stayed at #1 in the U.K. for 10 weeks, coinciding with severe flooding. They called it “The Rihanna Curse”. 

ARCHIVE: She’s here to make it rain right now, fellas I’m gonna need you to grab your umbrellas and welcome Rihanna to the show. 

ARCHIVE: And there you are 19 years of age and breaking through at that level already, fantastic success. 

ARCHIVE TAYLOR SWIFT: And the Grammy goes to…Rihanna ft. Jay-Z for Umbrella! 

Brandon Pope: This song won her her first-ever Grammy. And the hit is now listed as #332 on Rolling Stone’s 500 greatest songs of all time. 

Brandon Pope: Man, "Umbrella" that takes me back right there. Now Bill, what was it about umbrella that really kind of pierced the cultural fabric and made it pop the way it did? 

Bill Werde: I think there's a couple things about "Umbrella" that make it succeed the way it does. Like first and foremost, I don't want to bury the lede here, it's just a phenomenal production. Like it's a phenomenal song. Everything from like, her vocals, the way she sort of like sort of sing wraps, some of the lyrics, particularly like the you know, "stick it out till the end part." These things just really stick in your head. You know when you look at the best and most iconic pop songs, more often than not they deal with fairly universal themes. Because really, at the end of the day, what you're doing is you're providing a soundtrack for people driving in their cars, at least in America. You know, ride or die is is a powerful theme. It's very sort of simultaneously, like powerful and comforting. And it's one of these things where it's, it's kind of a universal truth that everyone is going to respond to. You also have this moment where you have Jay-Z, not just signing her, but now literally co-signing her on the video, which is I mean, you know, that's Jay really extending himself. That's Jay like, you know, with the biggest co-sign of all. And, you also have this repositioning, right? The whole era is this Good Girl Gone Bad concept. And here's Jay-Z, you know, one of the ultimate bad boys in a certain context, on this video for this artist who we previously thought of as kind of like, you know, a cute pop-star. And here's Jay setting it up as you know, Good Girl Gone Bad. Literally what he says right at the beginning of the video. Also, the last part of this is the video which is just incredible, right? I mean, the video itself has become iconic. Yeah, a little bit of a perfect storm there. 

Brandon Pope: Evan, take us behind kind of the the business story behind umbrella what was going on behind the scenes that led to this huge pop culture moment.

Evan Rogers: So the album, you know, being Good Girl Gone Bad. There was definitely a statement already that we knew this was sort of the growing up the next, you know, her becoming a young woman. And when that song came in, I think we felt she'd found her or her identity. A lot of the previous singles have been pitched in higher keys, which I think being a young teen artists, songs get thrown, you know, and they were hits SOS, Unfaithful. You know, great songs. But I think we always felt from day one, that she had a richer, lower part of her tone that really allowed her to shine on "Umbrella." Everything came together. It was the... It was the comfort zone where she could show that swag in her voice. Everything began to change quickly when that song hit.

Brandon Pope: Well, especially when you got Jay-Z, who was in his retirement phase in a sense, endorsing the track. Right? That adds a whole new level. 

Evan Rogers: Yeah, I remember the day that Jay Brown called us and said, I want you guys to come down. I'm going to play you something he didn't tell us what. Because we'd already heard the finished song. You know, we loved it. And you know, this is it. This is the first single and then when we walked in and he just press play, and we heard Jay do the intro. It was like, okay, you know, now now it's it's really getting real, you know, now it's on.

Bill Werde: It would have been so awkward and funny if you guys had heard that and been like, meh, that's not for me. Not only because like, you know, Jay Brown is like one of Jay-Z's like real lieutenants. Right. So there's a little bit of like a dynamic there. Like if you just hit play, he had been like, oh, no, that's whack. Like...

Evan Rogers: I will tell you though, that L.A. Reid – I'm pretty certain this is true – that he told me this that when he heard Jay's first verse, L.A. said, you can top it. Because we got... The first verse from Jay-Z was not the one that became the one. And it was good, but we loved it. But L.A. pushed him and he did another verse. And that became the one that went on the record. So we have versions laying around with the original Jay-Z intro rap. But that was, like just saying you can make it even hotter. You know, that's how it happened.

Bill Werde: Can I say like, I think there's something really brilliant there. Because again, everything has to line up for there to be like this, this massive hit. Right. And L.A. Reid has been, you know, controversial in the business for a number of reasons. In the last whatever years. That guy knows how to tell a story. Right? And that's, that's what that was about, right? Like, I think about pop stars a lot the same way I think about like, worldwide wrestling wrestlers, they all have their narratives and their stories, and the ones that are really gonna pop and stick around. Like, you got to get the right song at the right moment that kind of fills that story moment. And I think that's what, that's what Jay did with that verse a little bit. He positioned it that way. 

Brandon Pope: Alright, editor Chioma Nnadi, Let's bring you in here. You’ve followed Rihanna’s career and did her Vogue maternity shoot. When you look at that umbrella video, and the looks that she had there. What stood out to you?

Chioma Nnadi: You saw that sort of darker edge come to the fore. Before, she had this very cute look with the ripped jeans and the waves. And here she is, you know, she's on heels, she's she's in this, you know, this, this, this body skimming look, and you see her in a much more kind of this dark, more sexy attitude come to the fore. And I think she's always been a person who embraces risk and likes to do what people don't want her to do. You see that she enjoys transformation, how she presents herself and taking on different characters and flipping the script, and it's kind of interesting to see someone so young do that, because I think she definitely grew into her style, I think, she definitely continues to raise the bar, you know, each time. But it's interesting to see someone so young, so self possessed, and so... really understands the power of that image, as well as the power of this sound. 

Bill Werde: The other thing it does, which a lot of great pop songs have done over the years, is it walks this line between like, where it's where it's dropping some entendre, let's say, right? So, you know, you get to the end of that song. And it's like, it's the chorus, it's raining. Come into me. But there's a whole long history in pop music of men and women dropping lines that are like, wait a minute, like, hmm? Wait a minute. What are we singing about here? So I'm not sitting here saying like that was you know, do I think it was intentional? Do I think that there was an awareness of an entendre they're like, probably, I mean, let's not forget, the song starts off with Jay-Z saying Good Girl Gone Bad. So like she's, I think, throughout this album in general. And certainly her next album, you really see her start to begin to experiment with more, with more overtly sexual themes, and kind of grow into being a grown woman 

Brandon Pope: Evan I’m curious, do you agree with that? 

Evan Rogers: Absolutely. Rihanna was... always had an edge to her from day one. I mean, on her first album, we had a song called "There's a thug in my life, how am I going to tell my Mama," and we were like, she can't do that song. And she was like, no, I want that. And she was like, oh, okay, you know, and so, I think that with everything from the title of the album, Good Girl Gone Bad, to those lines in that song. You know, it was no accident. It's who she is, you know, she is an edgy person. She is a risk taker. And, everything from the changing of her hairstyle for that album, you know, that was a lot of pushback from the label, you know, she can't have short hair, you know, the bob with the angular like that was - she knew what she wanted, that album was definitely like now you're gonna see more of who I am growing into a young woman.

Brandon Pope: Just a few years later, something happens in Rihanna’s personal life that becomes international news. Let's play the clips. 

ARCHIVE CHRIS BROWN: I’m looking for the one with the glass slipper, baby girl you can be my Cinderella… 

ARCHIVE ABC NEWS: The singer on top of the charts and on top of the world, and then last February she was physically assaulted by her equally famous boyfriend, always known as one of the nice guys, Chris Brown.

ARCHIVE GMA: I am strong. This happened to me. I didn’t cause this, I didn’t do it. This happened to me and it can happen to anybody. There are a lot of women who have experienced what I did. But not in the public, so it made it really difficult. 

Brandon Pope: Now Chioma, this is an incredibly tender period of time for Rihanna and her loved ones. What was going through your head during this moment? 

Chioma Nnadi: I mean, you know, I think how incredibly brave she was, and how she responded to this moment, I think was pretty incredible, because I think she's had to endure all of this do with the public eye. You know what so many women go through. And I think it showed her resilience and her her ability to sort of be vulnerable to and to talk very candidly about something that was a particularly difficult moment to navigate. I remember the interview with Oprah. And, you know, you could see the sort of anguish and the the sort of pain that she'd been through. 

ARCHIVE RIHANNA ON OPRAH: So I think that when the world saw that in 2009, that’s what stuck with so many people. Absolutely, but nobody could feel that more than me. It happened, it happened to me, and it happened to me in front of the world. It was embarrassing, it was humiliating, it was hurtful. It’s not easy. I lost my best friend, like everything I knew switched, switched in a night. 

Chioma Nnadi: But she was brave enough to sort of speak on it. I think she understood that it was important that she did for other women, to raise awareness. And I think she's had to endure some very difficult moments and perhaps this was at a sort of moment for her that she really had to sort of find a way to be at once kind of - protect herself but also to be vulnerable. And I think it's a really difficult balance for someone who's in the public eye to strike. I don't think many celebrities are able to do that. And it's something that's very special to her. And unique to her.

Brandon Pope: Now, Bill, there's also value in understanding what this means for her public image. So in terms of how she was perceived as a celebrity, as an icon, what changed? 

Bill Werde: Wow, so this is obviously a lot to unpack. It's obviously a very triggering thing for for an incredible number of people. And I think first and foremost, it's, it was an awful, awful thing to have happened to Rihanna. I think a couple things to understand from a public image perspective: One is, you know, this happens after the Grammys. So you already have this moment where all attention is on music, or at least in you know, in terms of pop culture, all attention is on music. And suddenly, the story shifts, and now instead of talking about the Grammys, this is the story that they're talking about. So that's number one. And I don't mean to be, you know, gross about that. I mean, again, I don't want to bury the human element here. This is a person who experienced a traumatic thing. 

The other part of this is that, you know, at first, it's a news story, it's words, and then someone leaks, the images. And so then there's this like, next round. And so now those are going all over the world. And the you know, another factor to keep in mind here is this is relatively in the early days of mass social media. So things like this, like suddenly, for the first time the narrative can't be controlled by the powers that be because the narrative is being created on social media, by people that are consuming this and sharing thoughts. And so, I'm sure that we would all want this to have happened in a different way. But even as big as "Umbrella" was, things like this, when they happen, they do have a way like, people's grandmas were talking about this, right? This was major news. This was no longer like, I'm a fan of the pop charts, or I love pop music. Of course, I know who Rihanna is. Suddenly, she's hitting the radars of millions of people around the world, 10s of millions of people around the world that may not ever even listen to pop music. 

Brandon Pope: Now Evan, you know, you're her uncle, you know, she's an extended part of your family. Tell us what you're thinking and feeling when you reflect on this time.

Evan Rogers: That was a painful chapter. We were all at the hotel, in Hollywood, you know, night before the Grammys, and so the morning, early in the morning of the Grammys, woke up to these calls. Just craziness and at first not getting the whole story and, and then the realization of what had happened, you know, kicked in, and, you know, there had been whispers of, there's been some shows canceled, you know, leading up to it, and little whispers of what's going on, you know, behind the scenes. We had gotten to know Chris Brown and seemed like, you know, totally, like they were happy together and fun.

So, shocking, and hurtful. And, and I'll add one other angle, which was particularly infuriating to myself, and my team, was the amount of blame being pointed at her as this unfolded. Like I was, I guess I should never be shocked. But it was I, you know, with social media and everything, but, you know, there was a fair amount of people, you know, pointing the finger at her. She, she, I heard that she did this to him, I heard that, you know, which made it a painful situation much more painful. And I can only imagine how that made her feel. But it was a whole process. You know, that took a lot of a lot of time to, to come back from - sometimes you think you're over something like that. But it, I'm sure is that, you know, a life changing experience to a horribly traumatic thing. 

Brandon Pope: Evan, you mentioned that vitriol that, you know, was going around about her at this time from some, but there was also a lot of love and support that was being shown as well. Bill, can you zoom out for me a little bit and talk about America as a whole. What does this incident teach us about how fandoms shifted during a tragedy? 

Bill Werde: Well, you know, like I mentioned, this is sort of um... this is still the relatively early days of mass Twitter. This is also the first year or two, really, of this concept of fan armies are merging. I mean, it's actually really fascinating. I mean, you look back now, and this kind of like, like Ride or Die mentality. This like, I am able to refute any logic, any fact that doesn't fit my narrative of how I see my favorite artist, which is what's going on here with like, Chris Brown had his fan army. And they were not willing for a lot of these people to just take at face value, what what we were seeing and so I suspect strongly a lot of these attacks. And I still see this today, like Chris Brown fans that are like almost radically defensive about the criticisms that get levied against Chris Brown. But you know, you almost see echoes of this, right like that, that pop fans were the first to organize. Pop fans were the first to to kind of create these mass movements of support.

Brandon Pope: I think it's fascinating too, just how fans have in that moment have become more protective over artists. You mentioned these stanhoods, you know, now we see Cardi B's got her Bardi Gang, you got Nicki Minaj has her her Barbs, The Beehive, you see them all over social media, it becomes more than just passively listening to music, right? But an actual like, you know, an identity that you kind of embody? 

Bill Werde: Yes. And I will say, of all of those of all those fan armies, I got to give a shout out here to Rihanna's Navy. Because you know, you talk about Ride or Die, you talk about power, you talk about people that you know, are going to have the support of their favorite artist, and Rihanna's fans are up there with any one, literally anyone, in terms of being the most passionate, the most dedicated, and I'll say this to someone who's been active on Twitter since that time, you don't want to cross them. You know, and by crossover, I mean, like say anything that might be perceived as remotely critical of their favorite artist or you're going to spend a couple days like wishing your timeline was still usable. Uh because, because, you know, I see I see Evan laughing like, you know, you know what I'm talking about, like...

Brandon Pope: Bill, Have you have you been on the wrong side of these armies before? 

Bill Werde: I have, I mean, plenty of times. I don't know about... I don't think I've ever been on the wrong side of Rihanna's Navy specifically, but I definitely ran afoul of like Gaga's Little Monsters a few times, and barely lived to tell about it. 

Brandon Pope: I myself have survived the Barbs of the Nicki Minaj dive on Twitter. So I completely understand.


Brandon Pope: More Making, in a minute … 


Brandon Pope: By 2014, Rihanna had become much more than an international pop star. 

ARCHIVE RIHANNA CFDA 2014: I grew up on a really small island and I didn't have a lot of access to fashion, but as far as I can remember, fashion has always been my defense mechanism. Even as a child, I would - I remember thinking, she can beat me but she cannot beat my outfit.

Brandon Pope: It started as it always does with celebrity fashion stints: with her striking public looks. 

ARCHIVE MET GALA: Rihanna! O-M-G, my girl Rihanna finally on the red carpet at the Met Gala, we have all been waiting for this moment. Rihanna! Rihanna! 

Brandon Pope: She was named fashion icon of the year in 2014, dressed from head to toe in Swarovski crystals. Then...

ARCHIVE NEWS: What’s the big news with Rihanna? Oh, she just became the new global brand ambassador for Puma, that’s all. 

Brandon Pope: But being a brand ambassador with the best shoe was not enough for RiRi. She had to make waves in the industry. In 2017, she rolled out the Fenty Beauty collection. First, makeup… 

ARCHIVE NEWS: Rocking the makeup world, the first line to include over 40 different shades. 

Brandon Pope: Then lingerie… 

ARCHIVE NEWS: And some fashion critics are even saying her show is a pointed critique of that other colossus of women’s underwear, Victoria’s Secret with Victoria’s Secret sales down. 

Brandon Pope: And finally, in 2019 she solidified her status as a mogul, launching Fenty with LVMH, the largest luxury conglomerate in the world. And she just kept climbing… 

ARCHIVE NEWS: Rihanna is now the youngest self-made billionaire woman in the U.S. 

ARCHIVE NEWS RIHANNA: You know it was real weird getting congratulations texts for money, But it made sense when I realized it was inspiring to people that they felt like this is something they can achieve, knowing where I've come from, knowing my humble beginnings, they see the possibility and it gives them hope, and that made me feel really happy. 

Brandon Pope: Chioma, let’s rewind real quick to Robyn Fenty growing up in Barbados. When she was a kid, did she already kind of plant the seeds of her fashion interest? What did she learn from Barbados that she carried with her into the fashion world? 

Chioma Nnadi: Yeah um, you know she, all of her friends kind of went to her for fashion advice. And her aunt had a store. And, you know, she was the girl that everybody wanted to be dressed by. And she had a natural instinct for fashion. And then I think, that probably came from spending hanging out at her Aunt's store. But it's probably really innate to her, you know, I spoke to some of her some of her childhood friends recently. And they they sort of said that she was, you know, that she would all style them, which I thought was pretty sweet.

Brandon Pope: Yeah, that is pretty sweet. Fast-forwarding a decade later, she’s Puma’s brand ambassador, she’s coming out with radically inclusive lines. And she’s really caught your eye. What is she doing in fashion that makes her a big deal?

Chioma Nnadi: I think she has the ability - you know, she just can anticipate the moment. She understands what we want before we know we want it. Because she has so much fun with fashion. I remember meeting her interviewing her backstage for her first Puma show. And you know, she notices what other people were I remember she she she knew I was wearing. I think I was wearing sort of vintage on Bugatti. And she noticed and, you know, she, she is a fashion nerd like she, she loves it, you know. And you see that come through in everything that she does, you see that like she's obsessive about these things. And I think she came through at a time when we weren't seeing pop stars at that degree being multi hyphenate. There were a few that had tried their hand at fashion. But nobody had succeeded in the same way that she had. Because she really, she really has the right instincts. You know, I engaged with a conversation with her recently for the cover of Vogue. And I sort of suggested that maybe her what if a child didn't love fashion and she  was just peals of laughter because she just was like, that's not possible. My child has to love fashion. You know, it's like, it's a it's a language for her. It's an it's a mode of expression. It's her first line of defense. It's like her joy, like, it's part of how she communicates to the world. So it was no surprise to me that like, she was really leaning into it and made it something bigger.

Bill Werde: Brendan, can I add one little detail, that I think echoes or maybe supports a little bit of something that Chioma was saying? Probably around 2010, we had this business partnership idea that we wanted to pitch, That Billboard wanted to pitch. And I remember reaching out to rock nation and Jay Brown. With Jay it was well, you know, I kind of like the idea, but we need to get you you know, in front of Rihanna. And I was like, surprised. But Rihanna. I mean, she, you know, I presented this to her, she asked a dozen sharp questions. So hands on, so involved in her business. I think a lot of fans have this perception that all superstars with like other lines of business, just have, you know, smart corporate people making these decisions for them. But this is 100% Rihanna, nothing happens as far as I've ever seen in her camp, nothing happens with Rihanna's business with without Rihanna being in the weeds, making those choices, you know, and it's just so incredibly impressive. 

Brandon Pope: Chioma so many celebrities, you know, they try to do the fashion thing, but you mentioned the strategy that Rihanna had. Can you speak to how that compares to kind of what other musicians do and why that strategy and intention really matters in the fashion game? 

Chioma Nnadi: I don't know if it's like so much strategy as kind of innate sense of style and instincts. She also really knows her body so she knows what she needs and when she doesn't get what she needs, whether it's the lingerie that was missing, the foundation that wasn't available. Well, then maybe that that's an opportunity right? So I think, you know, she she grew up seeing her mother do her makeup and knowing that, you know that there were certain colors not available to black and brown women. And it was fulfilling a need, like, you know, it was the same when she loves Savage they weren't, you know, she got to take that amaze me that amazing speech to accept the CFDA award...

ARCHIVE ANNA WINTOUR: I'm so pleased to present the 2014 CFDA Fashion Icon award to my tweeting buddy, Rihanna. 

Chioma Nnadi: And you know, at the time, there were no, there were no panties that were her her shade of nude. And so she had to wear these, this underwear that wasn't quite right. And it was from there that the idea to do the Savage came from because she was like, Why? Why doesn't this exist? Like, why don't women who look like me have the options that they should have? So, so obviously she loves it, but she's smart, you know, like, she's not she's not a billionaire for no reason, you know, she's built something from sort of anticipating these things, and being totally connected to the, to what's going on in the culture, which I think is very difficult to do. That's where she has managed to sort of outshine so many of these other celebrities who have not, it doesn't come from an authentic place, perhaps, you know, when other people do it. 

Brandon Pope: And that impact of Fenty I mean, you know, I talked to women all the time black women, Latina women, who for them, it's deeper than just vanity, it's way more than vanity, it's about having yourself seen. Being represented, right? To absolutely just be yourself and have products that reflect who you are at your core. And it seems like that's what Rihanna was able to tap into that no one else really did. 

Chioma Nnadi: 100%. And it really came from a place of like, of A: of need like that this thing doesn't exist, and B: of like real instinct and, and style kind of accused like she has it. 

Brandon Pope: As we know, Rihanna just gave birth to her baby boy. Talk to us about her movement in maternity fashion. 

Chioma Nnadi: Yeah, you know, I kind of was lucky enough to sit down with Rihanna in, in Paris over dinner. When she was about, she must have been about seven months pregnant. And she was loving it. She was loving it. I walked in, she was tucked away in the corner. Nobody was kind of paying any attention. She was just there alone. And she just talked about how much she's enjoyed this, how much she enjoyed being pregnant because it sort of presented a challenge and she loves nothing more than a challenge. I think for a lot of women, it was such a sort of, they've sort of breathed a sigh of relief. Because women are told to hide, you know, women are told to hide. And it's a moment where you're sort of like always trying to disguise the bump. And here she was kind of fully, putting it on full display, like, I was at the Dior show when she walked in, in this sort of see through baby doll dress with a with, you know, her own design lingerie, which was like, basically dental floss. And it was incredible. I think she's managed to shake up that world, in maternity where... never had a sexy ring to it. And I'm sort of like, you know, sad. It's only nine months. 

Brandon Pope: Evan, there's rumblings from the Navy, and many others about a reggae album, what do you think is the next best move for Rihanna? 

Evan Rogers: Hmm. Um, she's in a position right now where she doesn't have to do anything. And I think as we keep referring to her instincts, and her sort of ability to know the right moment, to make the right move. I obviously am curious to see what happens. I'm like everybody else I'm waiting. I'm a fan too. I can't wait to hear, but one thing I know it'll be right when she says it's time. There's certainly no need for her to rush anything. She can do whatever the hell she wants. 

Brandon Pope: Well, thank you to our amazing panel here for your time and having this great discussion with us. That's making Rihanna thanks for listening and thanks to our great guests. Choma Nnadi, Bill Werde and Evan Rogers. 


Brandon PopeMaking Rihanna was produced by Heena Srivastava and Justin Bull. I’m your host Brandon Pope. Our executive producer is Kevin Dawson. Special thanks to Tom Breihan and Melena Ryzik for help on the show. More episodes are on the way. Be sure to press the subscribe button. And we’ll see you next week.

WBEZ transcripts are generated by an automatic speech recognition service. We do our best to edit for misspellings and typos, but mistakes do come through.