The Untold Stories Behind the Songs That Changed Everything

1 Oct 2026 · 22 min · 8 chapters

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In short

Black History Month episode where Estelle and Akon explain the behind-the-scenes stories of songs that became cross-generational “forever records,” and how songwriting choices, business strategy, and life events shaped their careers.

Guest backgrounds

Estelle is a UK-born, Atlantic Records–era songwriter/performer who credits vocal training and Motown/Supremes influence. Akon is a Senegalese artist who served about three years in jail, later building a long-term plan and a business approach to music.

Key claims

Estelle says “American Boy” was built for joy and singability, including a “Diana Ross/Supremes” vocal direction; it took years of practice to land a short, iconic hook. Akon argues ringtones predicted music’s digital future and influenced how he writes choruses.

Notable examples

Estelle recalls sessions with Will.i.am and notes from John Legend; “American Boy” peaked at #9 on Billboard Hot 100 and won a Grammy. Akon describes “Locked Up” becoming an in-prison anthem and explains how “Mr. Lonely” drove international crossover (e.g., Germany audiences singing despite language barriers).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Behind the Iconic Songs

0:45 to 2:53

Estelle shares the story behind her iconic songs and the creative process involved.

“And I said, if this isn't a hit, you're gonna make your money back because I'm going to Ibiza with it and I'm gonna make you your money back.”

The Impact of Music on Generations

2:53 to 5:10

Discussion on how songs resonate across generations and the joy they bring.

“It was genuinely, we were just in there like talking shit.”

Akon's Journey and Vision

5:10 to 7:17

Akon discusses his life, the vision he created while incarcerated, and the significance of his music.

“It takes you 10 to 20 years of studying, of practicing the house, of singing every minute I got, annoying every single person around me, annoying myself.”

The Business of Music

7:17 to 10:15

Akon explains how he approached the music industry as a businessman and his insights on monetization.

“It was like, it was all intents and purposes.”

Lessons from the Industry

10:15 to 14:00

Akon shares valuable lessons learned from his journey in the music industry and the importance of focus.

“Like, you know, sometimes some music you just have to...”

Akon's Business Mindset in Music

14:00 to 16:43

Learn how Akon leveraged ringtones to reshape his music strategy.

“Once I get this record deal, I'm going to get that money from a record deal, and I'm going to purchase an illegitimate studio.”

Akon's Rise to International Fame

16:43 to 19:10

Discover the pivotal moments that transformed Akon's career globally.

“Like, I didn't realize how much, how many albums you've sold.”

Realizing His Purpose Through Music

19:10 to 21:11

Understand how Akon reflects on his purpose and the impact of his music.

“When you think about your career, what was the moment where you just looked at it and said, this is surreal.”
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Transcript

Automatic transcript. May contain errors.

0:00Welcome to We're Talking. For Black History Month, we're featuring two songwriting heavyweights, Estelle and Akon. They reveal the stories behind some of their biggest songs, reflect on the moments that changed their careers, and discuss what it means to create songs that live across generations.

0:32At what point do you write the iconic... The Rhyme? That every... What is it? Ten years later, no, I was joking. But you wanted this, though. You wanted a song that you could sing to the end of time. In any country in the world. Any city in the world. I have a few of them, thank God. Come on now. Won't he do it? Won't he do it? When do you write? I wrote that in 2006 Okay, so you're in the States Yes You're signed to John Legend An Atlantic When he's like, come to Miami I've got sessions with Will.i.am I've got some shows out there Come on, cool Well, they set up a session with Will.i.am for me to be there too And he plays He plays the bass of it Not the intro, just the bass line of it And he's playing that whole thing And he starts running the track And I was like, run that back.

1:29What is that? He's like, I don't think. I said, no. And I said, if this isn't a hit, you're gonna make your money back because I'm going to Ibiza with it and I'm gonna make you your money back. I'm gonna go take this record. We're gonna release it in Ibiza. I had a whole independent plan for it. I was like, it's gonna be good. I'm gonna perform it. Just Ibiza. We're gonna make it just in Ibiza. I and Apple will love this, okay? Cause I know this. It felt like Garage. it felt like that vibe. Joe's like, what have you been doing out here? And I'm like, I've been on the beach. Because while you've been recording, I've been enjoying myself.

2:04I've been having a time. These guys loves me. These men love me. And I've been loving the men. It's been glorious. And he's looking at me like, such a child. I'm just like, absolutely. Like, I'm having a good time. He's like, well, come on, let's write the record. And he puts in, this time he did the melody. It's like, you know, like. And I'm like, yeah. And I was like, da, da, da. We back and forth on the different things. And then we filled in the words. One of his friends actually came up with the, we was like, don't like his baggy, but I might like what's underneath him. One of his friends said that, and I was just like, okay.

2:43Who are you, young sir? Like, what is this? Anyhow, I vocal a demo vocal with everyone in the room. And we're like, this feels special. Because it felt fun. It was genuinely, we were just in there like talking shit. Yeah, just having a good time. Having a good time. And then John leaves, you know. I stay in Miami a couple of days and I revocal it. It took me all the 15 minutes. Wow. I did it with the biggest smile on my face. I was just having all the joy. I was just like, but he gave me notes on it. He was like, you know, when you sing it, like, be bright. Like, I was just like, oh, that's easy.

3:19Yes. I can channel Holly from Heidi High. like all the British comedies and all the fun Ditsy. I was like, that was my channel. And then we would have all these conversations about the Motown lives and what made them great. And that was our other thing, it was music. And one of the things about the Supremes that no one really knows is like Diana Ross was put in the front. This is so the story goes. Diana Ross, I'm sure, will say something different, but she's put in front because her voice was light. It wasn't so gospel-y. It wasn't so black, right? And, you know, so the idea was like, well, just do a lighter version of the record.

3:59Sing it lighter. You know, like... Oh, that was a jealous note to you. Yeah, he was like, you know, sing it lighter. He said, remember the Diana Ross? And that was the conversation we were having. I was just like, yeah, let me try. Let me try. So when I sang it, I was like, I was in my Supremes. I was in there like... I was really like, I was really doing Diana, like, you know, in my head. Oh wow. And I was giving Polly in the like, I really want to, give it you. You know like going... Yes. I see it. Exactly. Think about how she would do like, can't hurry love, like in the, oh you just have to.

4:34The shoulders and the cleave, you know, the decolletage, like the whole like, that was everything I was giving. And so all of that intention went into that record. Wow. And it was just fun. It was the whole point. was like, I kept saying in the booth, I remember going like, this is going to be fun. People are going to have fun to this. This is going to be so joyful. You know, like, this is it. And that's it. It took us, like I said, 15, 20 minutes to hear it and left it and went home. That's the only point that almost feels disappointed to me. Look, but it takes you 10 to 20 years to get to 15 minutes.

5:11Okay? It takes you 10 to 20 years of studying, of practicing the house, of singing every minute I got, annoying every single person around me, annoying myself. Yes. Like stretching my vocal, like training myself to sing octaves that were not natural to me. You know, bronchitis, laryngitis, traveling, body folded over. I'm unfurling my body, getting in the studio, singing, figuring out to be 15 minutes and perfect. Yeah, it's incredible. In the research, I mean, you know this better than me, it was number nine on the Billboard Hot 100. obviously won a Grammy Award, Best Rap Song Collaboration, four times platinum in the UK, exceeding 2.4 million copies in the UK alone, five times platinum in the United States.

6:04Just like... Good time. It's a good time. Yeah. It's a good time. It just felt like it was buoyed by such good energy and goodwill too. And it lives forever. you know what's so profound to me about American Boy in particular is that so I have a 14 year old an 11 year old yeah right they know that song they know it a matter of fact you know I got I got the most number of cool points with them ever because I was like you know I've got Estelle coming on the podcast they said you've got Estelle I was like I know I know Estelle we go back like 10 plus years they were like dad why didn't you tell me you know Estelle because here's the thing my sisters feel the same about you, by the way.

6:47Oh, really? Yeah, they came to your, they come to your talks. They come, they're like, oh, they had a whole, I was like, yeah, they showed me pictures at one of your talks. They were like, we was at the panel. I was just like, all right, did you get close? Tell them I said hi. Yeah, I know. I was like, isn't this, it's wild. Yeah. It's wild, but the song, though, is, by the way, tell your sisters I said hello. I will. Yeah. They're going to see this. They're going to see it. Yeah. But the song, the fact that it is so profound to them, that means that you got this through time and the Kathy Sledge who I grew up looking at on a wall with my parents was on FaceTime with me in the Panini I call it the Panini, the pandemic she was like come on my show and I was like when would you like me there and with bells I'll be there and we get on Instagram live and she's like that's a forever record I was like it is it is like yours like yours like the many you have like the many like the many you have thank you you know will there ever be an American boy 2.0 no you didn't even give it a second no who wants that no no no no who wants that I want that you know what alright so let me let me give you this I gave them that and it wasn't me who wrote it it was it was me entertaining the idea from the label playing ball has a song called Fall in Love which I still like.

8:15It's just beautiful, melodic songs. Really cute. And I love singing it. But they didn't want it. It was like, it was all intents and purposes. If you go look it up, there's a song called Fall in Love. It features John Legend, and it features Nas. I have a record with Nas. John Legend and Nas. And nobody wanted that record. They didn't play it. They were like, eh, it's not American Boy. I was like, well, because American Boy is American Boy. Can I just do what I came here to do there? Yes. And then we moved along, and thank you. And then, you know, and here we are. Continue, Conqueror. One Love.

8:49One Love. Freak, like, you know. Yeah, obviously, I don't think that's your only forever record. No, no, no. There's a few. There's a couple. There's a couple. I got a couple. 98 will forever be one of the ones in the UK. I came out and I sang it the other day, and I barely had to sing it, and that made me feel like thank you, man. What would you guess my favorite is? Or one of my favorites? Kamuva? I mean, how do you, when is, why did you know that? Because it is, it's my favorite. Jamaica. Yeah. I think it's one of the best songs ever, ever written. Thank you. Ever written. Thank you. I probably play that song once a week, every week.

9:32So when you look at your streams, most of those are me. Thank you. Thank you so much. Thank you. I appreciate that. That's one of my joints though. oh my gosh man you like all you need is that and it looked like actually sunday is my favorite day to play that yes yeah and it's another intentional thing i make records for your life i don't want to just make it for the minute i want you to be able to be like i hoovered the floor playing this i was in the bathtub to this i was washing dishes to this because this is what i do and so i always want to make records that sit in that pocket for people i never want to just be the the hype, the pop, the whatever.

10:07I want to make records that you're listening to the words and you're feeling what I felt when I wrote it. Yes. Yeah. What I love too is that you can listen to it with the family. Like, you know, sometimes some music you just have to... This is me in the car by myself. Exactly. This is outside. This is outside music. But yours is inside and outside music. Yeah. You know, and I think that's beautiful.

10:43All right, now how long were you locked up for? About three years. Okay. I got out in 2001. Then when I got out, the first thing I did was go and start recording all the songs that I wrote when I was in jail. Okay. And then I realized that Locked Up was the first record that I wanted to release. because I felt like that was the moment that I was in at that time. And then Steve Rifkin, who I was assigned to over at SRC, kind of was with me, but Universal wanted to release Bonanza. That became the record that they felt like was the record. But you had the deal already when you were locked up or no?

11:22No. You had no deal when you had the deal. I had no deal when I was locked up. Okay. So tell me about the 10-year plan, though, because I think that's really interesting how you created basically a vision statement for your life. Yeah, the vision board. Yeah, so when I was in there, you know, I would just write on strength, right? And then I was writing Locked Up. And as I'm writing Locked Up, you know, every once in a while, I just kind of like sing it to myself to make sure I got what I want. And there was this older guy named Booney who was like my cellmate. And he would sit there and be like, Youngblood, man.

11:50What you doing here, man? All this talent, man. If you put all that energy that you had in them streets into your music, and you'd be, you wouldn't be here. Right. You know how big you could be? Right? You know how big you can be? And I was like, man, you know what you write. And then one day, we just happened to be in the pod. We was playing, I think it was playing Spades. Okay. And then Booney was like, Youngblood, sing that song, man. Sing that song for everybody you sung for me last night, man. Sing that song for me. Right? And I'm singing, I'm locked up. They won't let me out. Right? So then they was like, oh, that's your heart.

12:25That's your heart. Right? So now, every time a guard would walk past, we would sing the song out together. I'm locked up, they won't let me out, bitch. They won't let me out, Alada. Won't let me out, bitch. That's the original version, right? So then it became an anthem where every pod would sing it every time a guard would walk past. Oh, wow. And Booney was like, see what I'm saying? Look at this, man. He only sang this last week. This is an anthem in here now. Bro, I'm telling you, boy, you better focus, man. You better focus. He was an older guy. He's like 67. He's like, see, I'm telling you, man, if you don't do nothing else, if you don't get nothing else from here, just remember I told you, if you focus on that music, boy, that's your freedom.

13:07And I thought about it. I said, you know what? You're right. So I went out. I incorporated my company. I said, yo, Boone, I took your advice. I started my company, man. What you think? He said, yeah, what you named it? I said, Convict Music. He said, why the fuck would you do that? Convict Music? Man, that's the dumbest name I ever heard in my life. Oh, my God. I mean. Right? I said, nah, but think about it, Booney. You know, that's what inspired me, man, to do this, man. And this music is starting from here. And I'm telling them what I'm going to do. And I'm showing them. So I'm going to sit down.

13:39He said, all right, we'll put together a business plan and let me see it. And I put together a whole business plan. Then I wrote out what I wanted to do in the next 10 years. Okay. And what was on? What were some of those moments on the 10-year plan? The first thing, I wanted to record these songs. Okay. That was the first thing. I got to get me another studio and record these songs. That's going to be the first thing I do. Once I get these songs, then I'm going to go out and get me a record deal. Once I get this record deal, I'm going to get that money from a record deal, and I'm going to purchase an illegitimate studio.

14:06Okay. Right? And then from there, I'm just going to create a catalog. I'm going to write for everybody that needs songs. I'm going to be a writer, a composer. And if the artist stuff works, that's cool. But I know this part is a no-brainer because I know I got this. You just said something that I find really interesting. You said I'm a businessman. Right. So I've interviewed lots of, I say, exceptional musicians. And not all musicians qualify themselves as a business person. But the one thing that I was doing in my research that I said, I was like, nah, Akon's a businessman, is when I saw or when you realized how much money you were making on ringtones.

14:43Right. To me, that was fascinating. Could you talk about how that influenced your music? Well, I would probably say that kind of gave me an understanding of where music was going business-wise. I already saw it going digital. That's why I always retained my digital rights, because I saw then, okay, technology's changing and music is a part of that change, right? We were selling singles at the time for$1.99 for songs that was at length four minutes, some five, even seven minutes at that time. There was no timeline for how long a song was. Today, two minutes max. Right? And those was like$1.99. But then ringtones came up, and those were$5.99 for 15 seconds.

15:35If that. That was the longest a song was, was$5.99. I said, well, here we go. Something may add up. Or maybe it needs to add up. 15 seconds for$4.99, which is five bucks, or$1.99 for four or five minutes. It just made complete business sense to me. I said, I need to be focusing on ringtones. Every song that I make has to be ringtone-friendly while I'm not releasing it because I'm going to utilize not only the ringtones to promote myself, because every time the song rings, guess what? somebody's hearing a song, oh what song is that? And they go buy it. So you got walking billboards all over the globe with your ringer on their phones every time it rings.

16:16And that could happen 5, 10, maybe 50 times a day. Yeah, yeah. You know what I'm saying? So I don't need radio no more. I got ringtones. And then on top of radio? Yeah. Oh, forget about it. So when you're writing music, you're thinking... I'm thinking completely ringtones. Ringtones. Yep, I'm thinking ringtones. Okay, which part of this are we going to push out for the actual song? So I always thought about the chorus. So when I wrote the chorus, I said, okay, this chorus has to be at work on a ringtone. Okay, that's incredible. Yeah. That's incredible. Yeah. I mean, I could see that. Like, I didn't realize how much, how many albums you've sold.

16:49Not even until doing this research. Everything, it seemed like with the drop of your first album, everything just went platinum. Like... Yeah, it was, man, I was blessed to be honest, you know? I think it was, but believe it or not, the Africans was the ones that supported the most. like especially the first album, you couldn't walk through Harlem without hearing Akon. Senegalese was like that. You know what I'm saying? And then from there I went to the West Indians because I was doing a lot of dub plates. So between the Africans and the West Indians, it became like, they became like my mouthpiece, like my promotional tools.

17:27Like they, their word of mouth is really what got me even noticed, to be honest. Okay. But then from there, there was the crossover. Then it crossed over. When I got to Mr. Lonely, everything changed. Okay. Like, overnight. Overnight. That's what it felt like, at least. And how did it change for you? Well, for me, I started noticing that I was traveling internationally. Because before then, I was performing Locked Up, Trouble Nobody, Ghetto, domestically. And then I was getting a lot of dates in Africa. Those records was huge over there. And then I had a mixtape called The Illegal Alien, where I had Senegal, and I had all I had all the hottest beats at the time, and I took those and freestyled over them.

18:09So the mixtape was just as popular as the album and the singles. So with that, I was all over Africa. We was everywhere in Africa. And then when we dropped Mr. Lonely, then I was like, okay, this is different. Because now I'm getting called on pop stages. But what was crazy was the pop audience knew the Irvin records. Yes. They knew the Locked Up records. They knew the ghettos. They knew I was like, ooh, this is different. Then we would go to places in Europe like Germany, you know, Netherlands. You go to a place like Germany where nobody spoke English, but they sing the song from top to bottom.

18:47That's when things got really interesting. I wouldn't say weird, but it's funny because I would think that after I got off stage, I could have a regular English conversation with you. And they couldn't understand nothing. I'm like, but how are you singing my songs from top to bottom and we can't speak English together? Right. So that weirded me out for a minute. I was like, wow, this is different. That's when I realized, okay, God is special. Right. And you're blessed. Yeah. And you're blessed. 100%. When you think about your career, what was the moment where you just looked at it and said, this is surreal.

19:20I can't believe I'm doing this. I would probably say when the first time it actually happened, where I actually had that moment. because I kind of expected it in certain places. Like home in Senegal, I expected it, but it was mania, almost like Michael Jackson status. That's when I almost caught it, but I was like, well, I'm in Senegal. They're supposed to support me this way. It's like, you know. And when you say almost Michael Jackson status, you're talking about? No, like I couldn't go nowhere. Like literally, I couldn't walk down the street. I couldn't go to the local store. It would always be thousands of people waiting outside.

19:58Thousands. Like thousands. But when I went to Zimbabwe, it was like, wait a minute. Like from the airport. We couldn't leave the airport. Like we couldn't literally leave the airport. Like we couldn't leave the airport. Like the people would not leave until I showed my space. So they had a sunroof up there and I popped my head out the sunroof. I felt like I was in three stadiums in one. It was so many people for as long as you can see people. And I literally had to ride all the way to the airport on the roof. Because that was the only way I had to be there. I just tell people like... To tell people move out?

20:37It was like a sea of people. It was unbelievable. How does it feel to have that response to music that you create? That was another thing that was surreal. Like you're like, damn. My music is affecting this many people like this? That's when I realized, okay, I got a major purpose. Like, it's those moments that make you realize that, okay, everyone in life has a purpose, and your purpose is always going to be intangible with your gift. Whatever your gift is that God gave you, that's what's going to take you or walk you through the trail that you need to walk through to get to your purpose. And if you want to hear the full, unfiltered stories from today's guest, you can check them out on the We Need to Talk page.

21:19Drop a like, leave a comment, and hit subscribe. See you next week. Thank you.

From the publisher

For Black History Month, we revisit Paul’s conversations with Estelle and Akon, exploring the stories behind their biggest songs, career-defining moments and lasting impact on music. From Estelle creating “American Boy” in a Miami studio to Akon writing “Locked Up” while in prison, they share the stories behind some of their biggest records and the moments that changed their careers.

They also reflect on the work behind so-called overnight success, Akon’s 10-year plan for his future, the business opportunities he spotted early in digital music, and why both artists have always focused on making records that last. It’s a conversation about creativity, purpose, longevity and making music that connects across generations. We're Talking Music Legends

(00:00) Intro(00:33) The Story Behind Estelle's American Boy(05:38) How American Boy Became an International Hit(08:46) Paul's Favourite Estelle Songs(10:47) How Prison Inspired Akon's Songwriting(12:10) The Story Behind Locked Up(14:20) How Akon's Ringtone Business Changed the Music Industry(17:26) How Lonely Changed Akon's Life
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