Making Podcast Logo - 2022 REDUCED SIZE 1500x1500
Making Podcast Logo - 2022 REDUCED SIZE 1500x1500

Robyn Rihanna Fenty was just a 15 year-old student in Barbados when she showed up late for her audition with record producer Evan Rogers. Fortunately, her tardiness didn’t matter. She crushed it.

“I just heard something really unique and special in her vocals, even though they were raw,” Rogers said on Making. “It was just one of those moments where I think I have something really special here.”

This was just one of many critical moments we’ve dissected in this season of Making – the make-or-break moments that change the course of a life and often the course of history.

In this week’s season finale, host Brandon Pope takes a look back at some of the key put up or shut up moments from this season, from Serena Williams to Frederick Douglass to RuPaul and more.

Making Podcast Logo - 2022 REDUCED SIZE 1500x1500
Making Podcast Logo - 2022 REDUCED SIZE 1500x1500

Robyn Rihanna Fenty was just a 15 year-old student in Barbados when she showed up late for her audition with record producer Evan Rogers. Fortunately, her tardiness didn’t matter. She crushed it.

“I just heard something really unique and special in her vocals, even though they were raw,” Rogers said on Making. “It was just one of those moments where I think I have something really special here.”

This was just one of many critical moments we’ve dissected in this season of Making – the make-or-break moments that change the course of a life and often the course of history.

In this week’s season finale, host Brandon Pope takes a look back at some of the key put up or shut up moments from this season, from Serena Williams to Frederick Douglass to RuPaul and more.

Brandon Pope: What makes an icon? A superstar? A runaway success? It’s something we’ve been thinking about a lot this season of Making. Every week we’ve looked at an influential figure, talking with their family, their closest friends and collaborators, and there’s one thing that’s really stuck with us. For every one of these figures, it’s not just a matter of how, not just what, but when?

MUSIC - The Best is Yet to Come

Brandon Pope: Like Robin, Rihanna Fenty: When did her story change from: “island girl with a dream” to “island girl with a chance?” Or Jesse Jackson, whose childhood peers teased him, called him a “bastard child.” When did the schoolyard taunts turn from discouragement to ammunition? Or Frederick Douglass, enslaved and exploited, when did he alter the course of his own future? From WBEZ Chicago, this is Making. I’m Brandon Pope. And today, we’re looking back at some of the key moments from this season of Making. The supercritical “when” moments – the make or break moments, the put up or shut up moments that changed the course of a life, and oftentimes the course of history.

Ken Morris: The fight was everything.

Evan Rodgers: Do you want to come up and take a shot at this?

Barbara Ann Reynolds: He respectfully told her, “call me what you want, you’ll be proud to know this bastard.”

Larry Tee: It was that moment where everybody that saw the video, they went, “who was that?”

Gregg Downer: I just turned to one of my assistant coaches and I said, “This kid’s gonna be a pro.”

Brandon Pope: That’s coming up on Making, in just a minute.


Brandon Pope: Over this season of Making, there’s been something that’s really stuck with us. For every iconic figure we’ve profiled, there’s usually one defining moment, often early on in their lives, when everything changed. Today on the show, we’re looking at a few of those early moments. And first up, Rihanna.

MUSIC - Rihanna singing Hero

Brandon Pope: This is her at age 15, persuaded by her friends to sign up for her high school talent show. On the podcast, we spoke with the record producer who discovered her, Evan Rogers. When I spoke with Evan, I asked him to tell the story of the first time he met Rihanna. She auditioned for him in Barbados.

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 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.

MUSIC – Pon De Replay

Brandon Pope: One thing I love about this story is how Evan Rogers just right away, he saw talent and he just had to harness it. And Rihanna was that talent. That’s such a story that’s out of left field. Like a dollar in a dream type of story and I just love that. And I also love Rihanna in this moment. She walks in last, makeup done and outfit perfect. She came prepared to shine. And she knew this was an opportunity of a lifetime. You know, some people wouldn’t take it so seriously, thinking there’s always another opportunity down the line. But not Rihanna. And I just love that about her..


Brandon Pope: Now, our next make or break moment involves a civil rights legend, Jesse Jackson.

Archive: Pick up your slingshot! Pick up your rock! Declare our time has come!

Brandon Pope: He’s probably best known for his activism and his sweeping oratory.

Archive: Red yellow black and white, we’re all precious in god’s sight, our time has come!

Brandon Pope: He was also a serious contender for the American presidency.

Archive: Jesse Jackson for President!

Brandon Pope: Paving a path that Barack Obama would later follow in. But before all that, Jackson had a difficult childhood. He grew up in a racially segregated South Carolina. He didn't learn who his father was until he was seven years old. He was bullied by classmates for being “a “quote nobody” with “no daddy.” So, I asked his biographer, Barbara Ann Reynolds, if those schoolyard taunts affected him.

Barbara Ann Reynolds: I want to tell you just how deeply it affected him. One of his teachers, Mrs. Norris. She says I remember Jessie as a sharp dresser. He wore suits and ties when other students were wearing blue jeans. In fact, envious teenagers used to playfully tease him about his penchant for dignified dress. And he said one day, Jesse heard of front porch coffee sipper quip, there goes Noah’s bastard thinking he's better than everybody else. Look how he's dressed. And Jesse wheeled around and respectfully told her, “Go ahead, call me what you want. I am Noah’s bastard if that’s what you want to call me but one day, you will be proud to know this bastard.”

Brandon Pope: Wow.

Barbara Ann Reynolds: I had the privilege of going back home with him to Greenville, 1973. And his speech was remarkable. You know, I was there looking and I said, “Could this be him,” thinking about Jack the grocer, when he was eight years old, he went into a store and and he called for a white man to come and help him and the grocer held a gun to his head and said, Don't you ever demand a white man to do anything. Was he thinking about that man? Was thinking about the gossip monger who called him a bastard when he was 14. And at that moment, I mean in my own eyes, he looked almost angelic. And I said to myself, there, told you so. I told you I’d be the best damn bastard you've ever seen.

MUSIC - Carter’s Corner

Brandon Pope: The next defining moment we got for you is truly astounding. Frederick Douglass was born into slavery, he taught himself to read, escaped bondage, and then became one the country’s leading abolitionists and an advisor to multiple presidents. This, all in an era when many if not most of America thought of him as something less than human. When’s his critical moment? He was a teenager, devoid of all hope, when he decided to fight back, literally, in a battle with his enslaver. Here you’ll hear from Ken Morris, Douglass’ great-great-great grandson, David Blight, Douglass’ biographer, and Jeffrey Wright, the acclaimed actor who lends his voice to Douglass in the following clip. As a teenager, Douglass was sent to a notorious slave breaker, Edward Covey.

Audiobook: Mr. Covey had acquired a very high reputation for breaking young slaves, and this reputation was of immense value to him.

Brandon Pope: Douglass was whipped continually and treated barbarically for six months. Then one day, he resisted.

Audiobook: at this moment-- from whence came the spirit I don't know--I resolved to fight; and, suiting my action to the resolution, I seized Covey hard by the throat; and as I did so, I rose. He held on to me, and I to him.

Brandon Pope: They fought for nearly two hours before Covey relented.

Audiobook: This battle with Mr. Covey was a turning point in my career as a slave. I felt as I never felt before. My long-crushed spirit rose, cowardice departed, bold defiance took its place; and I now resolved that, however long I might remain a slave in form, the day had passed forever when I could be a slave in fact.

Brandon Pope: Now Ken, when I was learning about Frederick Douglass in school. His fight with Edward Covey was probably the moment that struck me the most as a kid. I remember I actually drew, I drew a scene with my crayons. Yeah, I drew a scene with my crayons of that. And I think that's what latched me on to the Frederick Douglass story to begin with. How important was this fight Ken?

Ken Morris: The fight was everything. It was an act of self liberation. And so when he begins to teach himself to read and write that was the first act of self liberation. But this battle, which was an epic, two hour battle, and Frederick knew that he needed to be strategic in the way that he went about defeating Covey. But when when he did, you know, he, while he wasn't physically free from his bondage, he was on his way to being mentally free. And he rose up, and he fought back. And so if you can just imagine this strong, brilliant teenage boy who had had enough. You know, this young boy, that's just saying, “Okay, I'm done with this.” A man has been made a slave. But now you've seen how a slave has been made a man

Brandon Pope: Ooh yes.

David Blight: Yeah, that's a resurrection story. We gotta remember how talented Douglas was as a writer. He sets up that whole scene, and essentially a biblical story. Because what precedes it is the story of him. He's just beaten to a pulp. He's lost his will. And he just cracks. And it just just takes Covey on. The fight becomes a kind of resurrection through violence, which is a very common theme in our culture. Americans love that resurrection through violence. So our man here knew what he was doing as a storyteller. But also it is the pivot of the story. Because after that, he's becoming a man.

Jeffrey Wright: I think what it represents too, it goes against. I think, the mythology of emancipation, you know, all praises to Abraham Lincoln and you know, we're waiting for the white savior, you know, to free the lowly enslaved. But it's Douglas exercising agency. If Douglas grabbing the beginnings of freedom, at least freedom of the mind. As described earlier to grabbing it by the throat, and it's about his own recognition of what is necessary and it's taking his future precariously, and literally, into his own hands. And he's doing that not solely against Covey, not solely against this one individual, but against an entire system. It's just a clearly incredibly powerful moment.

MUSIC - Cold Mountain Winter

Brandon Pope: We’ve covered an audition, a clapback to a hater, and a fight of biblical proportions. After the break, how a tennis legend gets discovered …

Rick Macci: I just decided to go out there and have a look. I never did it before, and I haven’t done it since.

Brandon Pope: Back in a moment.


Brandon Pope: Welcome back to Making, I’m Brandon Pope, and today we’re looking at some of the key moments in the young lives of the iconic folks we’ve covered this season. And that key moment for Serena Williams, arguably the greatest tennis player of all time, happened before she was born. How is that possible? Well, lots of parents send their kids to tennis lessons. But Serena’s father, Richard Williams, he took planning and preparation to the next level.

Archive CNN: What did you know about tennis? Nothing, no. You literally didn’t know anything about the sport? No. So how did you discover it? By watching television in Compton. And the TV we had did not have a remote control. And a guy called Bud Collins gave a girl named Virginia Rizik a check. I don’t remember how much the check was now, but I thought that is a hell of a lot of money for four days. I went to my wife and said we’re going to have two kids and become rich and they’re going to be tennis players. And she said, oh no. But we did, we had two kids. And I wrote an 85-page plan of Venus, I wrote a plan for Serena, of what I wish to do and how it would be done.

Brandon Pope: That was Richard speaking with CNN in 2015. The plans he made for his daughters, needless to say, worked. To explain how, I spoke with Serena’s childhood coach, Rick Macci, and I asked him about the moment that changed his life forever – when the Williams family convinced him to fly out to Compton.

Rick Macci: I actually got a phone call. And it was from Richard, you know, he told me I have two daughters, Venus and Serena. They're really good. And you know, you want to come to Compton, for whatever reason, and obviously looking back and I'm probably the only guy in the world saying their best vacation ever is Compton, California, that I just decided to go out and take a look. I never did it before. And I haven't done it since. I went out there. And that night met at the hotel room. Venus on one leg, Serena on the other. And then Richard, he pulls out a piece of paper and he started grilling me, I thought it was in a deposition. 

So then the next day he goes, we're going to pick you up at seven o'clock and we're going to East Compton Hills Country Club. So at seven o'clock, they picked me up in that bus. Okay, not a van. I get in the passenger side. Listen to this. I get harpooned in the buttock by a spring. I look in the back, there's a garbage ball hoppers, all kinds of dirty laundry and Meek and Venus are back there all scrunched up. I never called her Serena, I called her Meek. So about 15 minutes into the ride. I'm looking around, and I'm going this strange place for a country club. We pull up to a park, there's guys playing basketball–about 20 guys, people are passed out smoking and drinking. And they see Richard they go hey, King Richard, they call this guy King Richard in ‘91. So we go across the basketball court. It parts like the Red Sea. It was like they were celebrities, you know, like it was this Craziest thing. 

We go on to the court. So then we started drilling down, here's VW and Meek–arms, legs, hair flying everywhere. Beads are coming off their head, and I'm going what God's name am I doing in Compton, California. It was like out of control. Then I said let’s play competitive points. So once we started playing competitive points, the whole landscape changed. The movement was just crazy. They start popping the popcorn extra butter, the preparation got better, but the burning desire of both girls to get to the ball. They ran so hard, Brandon, their nose was almost on the ground. I never saw anything like it. And I went to Richard, I said, Richard, come here. And it's more about VW at that time. I said, you got the next female Michael Jordan on your hand. And he puts his arm around me. And he goes no brother, man. I got the next two.

MUSIC - For our Time

Brandon Pope: The story of a child with talent meeting the coach that changes their life. That happened to Serena Williams. It also happened in the Making story of our next subject, Kobe Bryant.

MUSIC - Memory box

Archive: The best player many believe in high school basketball. Kobe Bryant as you can see coming on the floor now.

Brandon: Kobe was born into a basketball family. As a kid he watched his dad Joe Bryant playing first in the NBA, and later in a pro league in Italy. He practiced, watched NBA videotapes and learned via osmosis. So when Kobe and his family returned to the US when Kobe was in middle school, the buzz around this young basketball phenom from Italy began immediately. And that’s when Gregg Downer, the basketball coach at Lower Marion High School in Ardmore Pennsylvania, decided to check him out.


Gregg Downer: I rarely ever will go down to a junior high game even to this day, but I went to watch him play and the coach was old school and pass it X amount of times where you might find a seat on the bench. Really not a lot of up and down not a lot of transition, not a lot of chances for really anybody to display their skills, let alone Kobe. So I didn't get a great look at him then. But the buzz was high enough that I invited him to practice on a weekend with, with our current varsity. And he came in there and he stepped into like a one on one drill. And he was just ripping people apart. And I just turned to one of my assistant coaches and I said this kid is going to be a pro.

Brandon Pope: So you invited Kobe to a high school scrimmage. He was in middle school when this happened, correct?

Gregg Downer: Mmhmm.

Brandon Pope: Well, and he was able to hold his own.

Gregg Downer: Yeah, I mean, we weren't great back then. But it's rare that a that a 13 year old just physically can can stay with a 17 or an 18 year old. And I knew I knew I had something really special.

Brandon Pope: What stood out was young Kobe’s exceptional work ethic. Here’s Kobe biographer Mike Seilski explaining how Kobe, still in high school, would prepare himself for the NBA

Mike Seilski: Kobe had a friend who was a couple years older than he was, Anthony Gilbert. So Anthony and Kobe would go around to basketball courts and playgrounds in and around Philadelphia, and play ball. Anthony had two jobs when he played with Kobe, number one was to rebound for him. And then the other job that Anthony had was to scream at Kobe, while he Kobe went through all these drills. You're soft, you couldn't play in the Public League, you go to a white school. Kobe wanted him to do this because he knew he was going to continue to hear this throughout his career in basketball. And he wanted to kind of don this emotional armor to be prepared for it to get ready to deal with it. There's a famous clip of Kobe's NBA career where he's standing in front of a player named Matt Barnes, who was playing for the Orlando Magic at the time.

Archive: Matt Barnes and Kobe Bryant say hello to each other.

Mike Seilski: And Barnes is going to inbound the basketball. And Kobe standing there guarding. And Barnes fakes as if he's going to throw the ball in Kobe's face. Kobe doesn't flinch. He does not move.

Archive: You're not gonna get into the head of Kobe Bryant. When you have a pillow flight and somebody fakes a pillow at you don't you at least flinch? Kobe Bryant that's the play of the game. He didn't even flinch.

Mike Seilski: I maintain you can trace a line from that moment, all the way back to those unique basketball games and workouts he was having with Anthony Gilbert that prepared him for a moment like that.

MUSIC - Overstanding

Gregg Downer: He is the winner of all winners. And he paid a steep price to become that winner. It was not a straight line. There were there were a lot of crooked lines in there. But to me, he was my Superman. And you know, it might sound corny, but Superman is not supposed to die.

Brandon: In our full episode on Kobe, we dive into the crooked lines that Kobe’s coach nods to there. Give it a listen. Now, this next icon we have for you truly changed the culture. He opened a million doors for queer people, young people, and so many others marginalized for their identities. It’s RuPaul Andre Charles. And note, Ru’s name was known long before he created the smash hit TV show RuPaul’s Drag Race. We looked at his explosive come-up in the 1980s. And the walk down memory lane took us to one particular moment when Ru hit the national spotlight.

MUSIC – Love Shack

Brandon Pope: It was 1989. RuPaul and his friends had just arrived from Atlanta, and they were the talk of New York City nightlife. One day, a friend asked RuPaul if they wanted to be in a music video for this up and coming band, the B-52’s. And he said yes. Ru later told Billboard, he didn’t sleep the night before because he was out dancing. He left the club, hopped straight on a bus and arrived at the set. I talked about this moment with his longtime friend and collaborator Larry Tee.

Larry Tee: You know, the love shack video was really Ru’s Farrah Fawcett moment. Because Farrah Fawcett was on a TV show, where she didn't really say anything. But everybody said, Who is that? I remember my dad, and I waiting for Farah to show up on this TV show. And in the love shack video, she plays a Farrah Fawcett role where you're watching the video and it's cute and everybody it's like, you know, a bunch of normies dressed up in 60s gear. And then there's RuPaul. Like doing this crazy dance, and it was that moment where everybody that saw the video and everybody saw that video. They went who is that?

Brandon Pope: You can see him in the video, leading a Soul Train line. He’s dressed in all white with a regal afro, towering over the other dancers.

Larry Tee: You know, I remember at the time, when RuPaul showed up, I thought he had like fallen out of the sky. He was just so different from Atlantans that we knew. Here was this fully blown rock star character that just landed fully formed. And, I mean, there was just nothing. There was nothing like him. There were no drag role models, there were no tall skinny gay dudes that knew they were going to be a star and they, you know, that would be the first thing that would tell you when you met them. It was practically, “Hi, I'm RuPaul I'm a big star.”

MUSIC - Half a chance

Brandon Pope: Thanks so much for listening to this season of Making. This episode is our season finale! We’re taking a little break, then we’re coming back next year to look at the origins of a whole new slate of influential figures. And we want to hear from you! Who do you want to hear on Making? Tell us. Email us at And once again, thank you, thank you, thank you. This episode was produced by Justin Bull and Heena Srivastava. Our executive producer is Kevin Dawson. And I’m Brandon Pope. Take care, and we’ll see you soon.

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