WEBVTT

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You know, there's this idea that music genres

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are these like super rigid boxes. Right. You've

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got your rock kids over here, your rap fans over

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there, and they just don't mix. It's like high

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school all over again. Totally. Historically,

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that was true. You picked your tribe, you wore

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the uniform, and that was that. But then you

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look at the last decade and you look at this

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one kid from Canton, Ohio, Michael Lamar White

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II. Who we all know as Trippie Redd. Exactly.

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And he didn't just cross the lines between those

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genres. He took a sledgehammer to them. A sledgehammer

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is a good way to put it. His discography is,

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it can give you whiplash if you're not ready

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for it. For sure. So that's the mission for this

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deep doc. We're trying to figure out how this

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artist became, I mean, almost a Rosetta Stone

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for modern hip hop. How did he connect the dots

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between, say, the angst of grunge rock and the

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swagger of Atlanta Trap? Yes. And how did he

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do all that while his personal life was basically

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a reality show? And we have to mention, secure

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a $30 million contract and basically invent a

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whole subgenre before he even turned 26. That

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age thing is just wild to me. Born in 99. It's

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early 2026, so he's only 26. But he feels like

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a veteran. He does. He's been shaping the sound

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for a decade. In rap years, that's like two lifetimes.

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To really get it, though, you have to go back

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to the beginning. Back to Canton, Ohio. Which

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is not exactly a music hotspot. It's the Pro

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Football Hall of Fame city. Exactly. And we're

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talking specifically about 14th Street. The 1400

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block. You hear him shout it out all the time.

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1400. Right. And that's not just marketing. That

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was his world. It was a tough place to grow up.

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He was affiliated with the Bloods pretty early

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on. See, and that's the first thing that doesn't

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add up. You hear Bloods affiliation and you expect

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the music to be. Well, you expect street rap.

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NWA, maybe some Chief Keef. Yeah. But his mom

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was playing Ashanti and Beyonce and Tupac in

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the house. A very soulful, very lyrical foundation.

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But Trippie himself, he was the kid in the corner

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listening to Kiss. Wait, Kiss. Like, face paint

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and pyrotechnics, Kiss. Marilyn Manson, Nirvana.

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Green Day, and then he'd switch right over to

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Gucci Mane and Lil Wayne. That playlist makes

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absolutely no sense on paper. Yeah. How do you

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go from simple plan to Gucci Mane? Well, think

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about the energy, not the instruments. What's

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Marilyn Manson about? Shock, raw emotion, being

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an outcast. Right. And what's Gucci Mane about?

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Rebellion, being an outsider, grit. To a teenager

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in Ohio, they're not that different. He heard

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the feeling, not the genre, a guitar scream and

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a trap snare. They hit the same nerve. So he's

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soaking all this in. But just listening to music

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doesn't make you an artist. There's usually some

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kind of catalyst, a spark. Or a tragedy. And

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in his case, it was a tragedy. In 2014, his older

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brother, Dirty Red, was killed in a car accident.

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And his brother was the one making music first,

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right? He was. And that death, it just flipped

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a switch in Trippie. He didn't just mourn. He

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sort of took up the mantle. He started recording

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almost right away. Putting out tracks like Sub

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-Zero and New Ferrari. Which he later deleted.

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They weren't great. He was still learning. But

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the intent was there. That voice he has. That

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strained, cracking, almost screaming delivery.

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That's not a vocal lesson. That's pure grief.

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He was rapping to process the loss. So he graduates

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high school, moves to Atlanta. Yeah. And that

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unique voice is what makes him stand out. Atlanta

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was everything in 2016. He connects with Lil

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Wap, gets in studios with Cody Shane. He starts

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to bubble. But the real explosion was May 2017.

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A love letter to you. And the single Love Scars.

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Love Scars is the blueprint for emo rap. Forget

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Wikipedia. Just listen to that song. Let's break

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that down, though. What is emo rap, sonically?

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Okay, so you have the bones of trap music, the

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rattling hi -hats, that booming 808 bass. But

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over that, instead of a traditional rapper, you

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have someone basically... singing or whining

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in the best way possible about being heartbroken.

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It's super raw. Sounds like it was recorded in

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a bedroom. Totally. And it's vulnerable, but

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it's also incredibly catchy. It went double platinum.

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Yeah. And it put him on the radar of the other

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huge figure from that time. XXXentation. You

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can't talk about that era without talking about

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X. They were the twin pillars of that whole SoundCloud

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wave. And Trippie was the only feature on X's

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album 17. The only one. On Fuck Love. A track

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that, I was just looking this up, was Certified

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Diamond. in 2023. 10 million units. That's insane.

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Most artists never get a diamond record in their

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entire careers. He hit that milestone so early,

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it proved he was more than just an internet fad.

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He was a real star. It really cemented his place.

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Then came his debut studio album in 2018, Life's

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a Trip. And that gave us Dark Knight Domo with

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Kravis Scott. Oh, that music video. It was like

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a zombie movie. It was pure chaos, dark, high

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energy. It was his first time on the Hot 100

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as the main artist, and it showed he wasn't just

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going to be the sad boy, he could also rage.

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Which brings us to the next chapter, the full

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-on genre bending. He starts leaning way more

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into that rock sound. He really does. In 2021,

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he drops Neon Shark vs. Pegasus. The Neon Shark

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part was a whole rock album produced by Travis

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Barker, the king of pop punk. The ultimate cosign.

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And for Trippie, it wasn't a costume. This was

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him going back to the stuff he grew up on. It

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felt authentic. But he didn't just look back.

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He was also pushing forward with this new sound

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people started calling rage. Rage music. Yeah,

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you hear that term everywhere now. Can you define

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that for us? It's not just angry music. No, it's

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very specific. It's high energy. almost frantic

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it's built on these buzzing distorted synthesizers

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that sound like an old video game like an arcade

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machine breaking exactly the loops are repetitive

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hypnotic it's music made specifically for a mosh

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pit and the prime example of that is miss the

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rage 100 with playboy cardi that song debuted

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at number 11 on billboard his highest chart position

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ever which is funny because it is not a radio

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friendly song it's abrasive but that's the point

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He knew his audience was raised on internet chaos

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and video games. He didn't make a song for the

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radio. He made a song for the festival and the

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radio had to catch up. And he just kept working

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with everyone. Drake, Lil Uzi Vert, even that

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EP with MGK in 2024. Genre. Sad boy. Which got

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some pretty mixed reviews. Mix is being kind.

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A lot of critics hated it. But it shows he's

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not afraid to try things, even if they don't

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always work out. Okay, we have to talk about

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the personal side of things now. Yeah. Because

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for a guy who thinks about heartbreak, his real

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-life relationships have been volatile. That's

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the word for it. Volatile. Okay, we have to start

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with the big one. Tekashi, 6 '9 by 9". Ugh, yeah.

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If X was like a brother, 6 '9 was the arch nemesis.

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They started out as friends, though. They had

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that track, Poles 1469. They did. Back in 2017,

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they were on the same wave. But then the allegations

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came out about 6 '9 and... Trippie just, he drew

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a line. He publicly denounced him. And it wasn't

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just Twitter beef after that. Not at all. It

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got physical. Trippie got jumped in New York.

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6x9 got jumped in L .A. There were threats. There

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were other rappers getting involved. It was a

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mess. Then it got even more serious during 6x9's

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federal case. Yeah. In court, under oath, 6x9

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named Trippie as a member of the 5 '9 Brims gang.

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He snitched on him. In federal court. He did.

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But look who's still standing, still evolving.

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Trippie outlasted all that drama. And his friendship

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with XX Tentation was also full of ups and downs.

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It really was. There was a point where X literally

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banned him from coming to Florida. That's so

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wild to think about now. They patched things

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up, of course. X apologized. But then came the

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tragedy. X was killed on June 18th, 2018. Which

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was Trippie's 19th birthday. Can you imagine?

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Turning 19 on the day your friend is murdered?

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That changes you. He dyed his hair in tribute,

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released songs for him. He still talks about

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him all the time. Loss is just a constant theme.

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Even in his romantic life, it's been public and

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messy. For sure. His breakup with Sky Morales

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in 2023 was all over the blogs. He even publicly

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apologized for cheating. Which is pretty rare.

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It is. But now there's the whole thing with Coyle

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Array. The ultimate on -again, off -again relationship.

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They dated years ago, broke up, and then got

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back together. together in 2024. And now it seems

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much more permanent. It does. They had a daughter,

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Miyoko, in June of 2025. He's a father now. A

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father who still has run -ins with the law, though.

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Right. We can't forget that. There were assault

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charges back in 2018. And just last year, July

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4, 2025, he was arrested at Miami International

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Airport. What a way to spend the 4th. Yeah. He

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had an active warrant for driving without a license.

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It's just a reminder that even with all the success,

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Old problems can still surface. And speaking

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of success, let's talk about where he is now,

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the current era. This is not the SoundCloud kid

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anymore. Not at all. He signed a $30 million

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deal in 2022, bought a $7 .5 million mansion

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in Florida. He's a mogul. Creatively, though,

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it feels like he's at a bit of a crossroads.

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I think so. Mansion music in 2023 got a lukewarm

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response, and that single he did with KSI in

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late 2024, thick of it. Oof. The internet was

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not kind to that one. No, it was. It was panned.

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And that's the danger when you're so prolific.

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When you put out so much music, sometimes the

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quality dips. You risk burning out your audience.

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But he's not slowing down. Right. We've got the

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new album, NDA, on the way. Right. We've heard

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a couple of singles. And the big news is that

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it's supposed to have a feature from Kanye West.

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Which is still a huge deal. A Kanye feature still

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means something. It shows he's still aiming for

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the very top. He's not just coasting. So let's

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sum this all up. He blended rock and trap. He

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basically birthed the rage sound. He survived

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all these insane feuds. And now he's a dad with

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a massive record deal. What's the takeaway? I

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think Trippie Redd is the guy who made it okay

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to be everything at once. He destroyed the idea

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that you had to pick a lane. He showed you could

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be a gangster rapper who also sings about being

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sad. He made it cool to scream your feelings

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over an 808. Exactly. The entire sound of modern

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melodic rap. You can trace so much of it back

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to him. He took the weird kids playlist and made

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it the mainstream. All before turning 26. Which

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brings me to the thought I want to leave everyone

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with. He did all this as a teenager and a young

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adult. He's a father now. He has the money, the

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house. He's got, what, another 20 years of his

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career ahead of him, potentially? But will the

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music change? So much of that sad boy and rage

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sound is fueled by youthful chaos and angst.

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Right. When you're not struggling anymore, what

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do you rage about? Can his sound mature with

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him? Or is he kind of trapped by the sound he

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created? Can you still make... believable rage

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music when you're a millionaire dad. That's the

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real question. Can you rage responsibly? We're

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about to find out with this new album. That's

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the whole story of the NDA era, isn't it? What

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happens next? We'll be watching. Definitely.

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If you haven't already, go listen to Dark Knight

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Demo and Miss the Rage. Essential tracks. Thanks

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for joining us for this deep dive. Stay curious.

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We'll catch you next time.