It is impossible for any musician, at any level, to 100 percent prevent the leaking of music. Beyoncé, Madonna, Radiohead, Kanye West and Harry Styles are among the superstars who’ve fallen victim to leaks of upcoming albums this century, and less than a year ago it happened to Taylor Swift, with The Tortured Poets Department. But in the fast-and-loose, run-and-gun world of underground hip-hop, where previewing snippets of often unfinished music weeks and months before a project drops is de rigueur, leaked music is a chronic problem.
No one in next-gen rap was more plagued by the scourge in 2024 than OsamaSon, the South Carolina-raised and now LA-based young gun. Born Amari Middleton, who thanks to a string of 2021-22 singles and two buzz-generating mixtapes, OsamaSeason and Flex Musix, made quick work of rising to the top tier of the scene, throughout 2023. Last year, it was poised to take the kinetic 21-year-old even higher – and it did, but it was far from according to plan. A series of leaks, including one in May resulting from a phone hack in which literally hundreds of tracks were stolen, made for a gutting time. Lil O’s only new music drops last year were a collab EP with Glozz40Spaz, a handful of singles, including the summertime stunner with aura prince Nettspend, “Withdrawals,” the fall tracks “ik what you did last summer” and “The Whole World Is Free.”
Still, anticipation built for OsamaSon’s third mixtape Jump Out, ready to go after several reconfigurations, until it too was leaked on Christmas Eve. So it was back to the drawing board for another track revision, followed by yet another leak in January, at which point O cut his losses and dropped the record, a few weeks ahead of schedule. Promo plans were upended, there was an anticlimactic feel to it – it was enough to leave a young rage rapper truly enraged, or at least bummed. But it was out, and the good news? After all that, Jump Out is a hit, at least by underground standards. It’s cracked the Billboard 200, it got a more-than-respectable 8.2 from Pitchfork, and O’s notoriously picky and extremely online fans have mostly embraced it.
Jump Out delivers more of the rowdy, dizzying cyclone of sounds OsamaSon’s come to be known for: wiry, swirling synths over 808s on the grind – the most bone-rattling tracks, like “Frontin” and “New Tune” are already fan favorites, but share space with the bright, tuneful “Made Some Plans” and “Luv.” O’s vocals are sometimes crisp and sometimes blurry and buried. And if every lyric isn’t completely discernible, that’s okay. Or, rather, that’s “ok,” as in, producer wegonbeok, OsamaSon’s right-hand man on Jump Out. There is no more in-demand beatmaker in the new wave at the moment. Two months ago, ok (William Minnix) was executive producer on Nettspend’s first major tape, Badassfuckingkid, and he assumes the same role on Jump Out, to even more compelling effect.
The two Carolinians (OsamaSon is from Goose Creek, SC, while ok hails from Charlotte, NC) partnered on 15 of the deluxe version’s 20 tracks, while the balance of the tape was done by O’s other longtime partners, members of the international beatmaking collective Draco.fm, including legion, skai, Warren Hunter and gyro. It’s a celebratory record, focused more on successes than frustrations, flexing harder than Flex Musix. “Lil O, big boss bully” the rapper proclaims himself on the quotable standout “I Got the Fye,” adding, “I don’t pass out no hugs, bitch, catch a slug.” Racks are in abundance on Jump Out, as is fashion. Women are needy and weapons are ubiquitous: Glocks, TECs, Dracos and MACs: on “Waffle House” he cleverly wields a MAC for “Mack” – a reference to London artist Phreshboyswag, an erstwhile member of Xaviersobased’s 1c collective with whom Lil O has had an extended, if inconsequential, beef.
Amari Middleton is not one to let music pirating chuds get him down for too long. He’s too busy continuing on an upward trajectory and Jump Out, with its confident, often taunting air, feels like an assertion that he’s ready to take another step up. In underground hip-hop, conventional wisdom holds there is almost no such thing as dropping too much music — a mixtape or EP twice, even three times a year, along with multiple loosies, is par for the course. Out of sight, out of mind, as they say: disappear for too long and the attention-challenged fans are on to the next one. So for OsamaSon to go for all of 2024 without a new project and still remain at or near the top of his world is remarkable. Part of that achievement is due to successful tours – he feels he’s leveled up his live shows, including playing at three 2024 Rolling Louds – and a wellspring of support from followers who sense he has much more to offer.
“They used to call me Lil O, hit a M, now I’m Big O” OsamaSon boasts on Jump Out’s “Logo,” and it’s hard to argue with him. With a Jump Out headline tour set to launch in late March and plans to spend most of the year wilding up mosh pits worldwide, don’t be surprised if this time next year, he is an even bigger O who’s transcended what anyone can reasonably call “underground.” Even Lil Uzi Vert has taken notice, recently posting a surprise snippet of himself rapping over Lil O’s “Freestyle,” sending the underground into momentary overdrive. Two days later, PAPER sat down in Lower Manhattan with OsamaSon.
O, I usually start by congratulating artists on their latest project but in your case it’s really congratulations, because I feel like you guys have had so much to overcome to get to where we are right now with Jump Out, with all the repeated leaks and reconfigurations and postponements. Do you feel even more gratified that despite all that the record has gotten a great reception these past few weeks?
Yeah. I’m not gonna lie, there’s actually been a lot of times when I’ve sat back and thought of this and I’ve been – I don’t want to say a depression state, but for a few months after everything that happened, that got leaked, I did feel like I was in a pretty bad space, where I didn’t feel like I was myself anymore. I didn’t feel like I had control over anything.
Around the end of last year?
More so the middle of last year, or I’d say around my birthday, in May.
When the big leak happened? [a reported 400 tracks]
Yeah, when that happened, the Iron Maiden shit started going on around the same time [the metal band reportedly threatened a lawsuit over O’s use of an image they claimed was too close to one of their longtime ghoul mascot, Eddie], there was just a lot of shit hurtling and adding on top of it. So I was in a pretty bad space. And it didn’t take me to realize that until towards the end of 2024, when I had people telling me like, “Yo, this isn’t the same Osama. This isn’t the same Osama that I knew that wanted this shit,” you feel me? It was like, “You letting this weak shit get to you.” And so I started to realize that I was letting it get to me too much. But at the same time, I was pretty mad about it, thinking, “Why did they do this to me? What did I do to deserve this?” On the good side, it was like – I didn’t really have to drop last year. Because of the leaks. And I don’t wanna say I’m blessed for that, cause I did want to drop. But there’s not a lot of people that can just go without dropping and have their music get received so well that they still score raves, no matter if they release it or not.
I have to ask you about what everyone’s been talking about in the past 48 hours which is this video of Uzi doing his thing over your “Freestyle” – did you know that was coming?
[laughs] Nah, I didn’t know it was coming.
So what was your reaction, and…
I mean, I seen it, I think I was in the car and falling asleep on the way to the hotel, until I got to the hotel, and people were tagging me and shit, and texting me – and I just wanted to sleep! I didn’t really know what was going on? Obviously I got a hell of a lot of notifications, and then I woke up and I seen it, and I was just like, “Oh, Uzi just exploded!” He was just goin’ brazy. I been knowing him for a minute. We got introduced by some mutual friends.
There was a rumor there last year that you guys might be collaborating.
Yeah I don’t know where the rumor came from, but that was around the time that we was locked in. But I didn’t tell nobody, or it wasn’t something that I wanted to announce publicly, cause I just don’t feel the need to do that. There’s a lot of people that have reached out to me, a lot of my favorite artists, personally, people that I have listened to growing up, especially in the underground scene. But I don’t feel the need to broadcast that, or show that to everybody, you feel me?
What new songs seem to be really connecting? I know I’ve seen a lot of fans talking about “I Got the Fye” and “Ref” and “Logo,” which is a bonus track.
It’s hard for me to tell you because, as I’m going through the comments, every time I check a song they’ll be like, “Aw, I know I said that last one was my favorite, but this one is really my favorite!” And I been checking that now, as the project has been out for like a week or ten days, people are coming back and they’re like, “Yo, I know I said this shit was ass, but I was tripping, this shit is really like top 10 on the tape!” [Laughs]
But the real heavy hitters, that I know for sure are knockouts, are “Frontin,” “Ref” – I feel like “I Got the Fye” is getting received a lot. “Southside” – I feel like a lot of people like the intro. Or you can call it “C-Note” – some people call it “C-Note.” Those ones – and “New Tune” – that was a snippet that people was wanting since I was on tour, cause I was previewing that while I was on tour.
When the big leak happened, last May, were you completely blindsided? Do you remember your reaction?
I was embarrassed. I’m not gon’ lie. I can tell you that I ended up getting a text from [veteran Atlanta producer] Zaytoven, on Twitter. It wasn’t Zaytoven though, it was somebody who had hacked into his account. And I thought it was really Zaytoven cause people followed him and shit, and I was like, “Oh shit this actually might be Zaytoven.” And they sent me a link, and I clicked the link and shit, and it was just ripped from there. But I didn’t know, literally until the next morning. I hopped on the beats that “Zaytoven” – quote unquote – had sent, all that shit. And I woke up the next morning, and it was like, “Damn.” And we were already going through a little bit of n—-s selling our songs and shit, leaking and shit, but that was just from people sending it around. Now they had my whole vault, my whole phone, everything in my phone, from my pictures to my notes to my messages and contacts. I woke up and they was telling me, “Yo they’re selling all your music! How’d they get your music?” I’m like, “It could only be one thing. I did text ‘Zaytoven’ last night,” and we just figured it out. We got in touch with his son, and he was like, “Yeah it was hacked.”
This might be a question that’s asking you guys to get into the minds of someone who would do that, but I’ve been covering piracy and/or leak stories for a long time, and I’ve still never understood what would make someone want to do that, other than, to prove that they can.
People just want to be known for something.
But you can’t seriously call yourself a “fan” and …
But they genuinely are fans, though, because these same kids will have me as their profile picture! These kids look up to me, brah, I’m not gonna sugarcoat it I’m texting the hackers that’s hacking my phone, and – I found the hacker that hacked my phone one time. And I go to his profile picture, right? And it’s literally me. And I’ve never texted this kid, he follows me, everything. I text him, right. I’m like, “Yo, how are you leaking my shit, you’re hacking my shit, but you’re a whole fucking fan?” And goes on to reply, “I barely even know you! I know nothing about you! I’m not a fan of shit!” He goes and changes his profile picture from me to some random. You feel me, so it’s like – they just don’t like being caught, but they are fans for real.
There are plenty of fashion shout-outs on Jump Out, and I asked [O’s publicist] Sam the other day if you had done any modeling, cause it seems like a natural for you. You’re 6’ 2” – you haven’t been approached to do any runway shows or anything?
Nah. I think I need a modeling agent!
But it’s something you would consider.
Yeah, but I mean I do have crazy anxiety, so I probably would be nervous to do it. I’m not gonna sit here and say, “I’m ready to just jump in and do it!” [laughs]
Sam: Well you killed it today!
Yeah. Well photo shoots is a little bit easier, you feel me. And I think I’m a pretty good-looking guy, I don’t think I really got any bad features about myself…
That’s why I’m saying you would be a natural! And so, as far as all the guns — the Glocks and TECs and Dracos and MAC mentions on the record – I will say there is a MAC, or “Mack” bar that keeps getting all the attention, which you posted about the other day, from “Waffle House,” I guess people who know, will know who – a certain Brit [Phreshboyswag] — you are talking about.
[Laughs]
That lyric – what is it, “I’m gonna spill his beans”? I don’t know, is that, do people make more out of that as a beef than there actually is?
It’s just a bar. [Smiles]
Yeah? So it’s not some serious like feud going on.
Yo, some people aren’t even allowed to leave the place that they’re in? So it’s like – you can’t beef with nobody that can’t travel. You feel me, so it doesn’t even make sense.
Fair enough. One thing there’s not a lot of on the record is drug mentions. There’s a “percs in my piss” line on “Going Dumbo” and a drank reference on “Made Sum Plans.” But that’s about it. And I went back and looked at OsamaSeason from two years ago and there’s X mentions, and Xan mentions all over, on like “Summer Sixteen” and “Werkin” – but I don’t see as much of that now. Is that a reflection of where you’re at?
It is, man! I’m getting older. When I was a kid, trying to do everything I seen, trying to be super influenced by the rappers. But now I’m an influencer and I’m getting older, so I’m not trying to rap about shit like that no more. I’m not trying to rap about being off X all day, and getting jet lagged and shit. That’s not even that cool, that shit hurts your body. Like, doing those drugs, you get a short, a quickness of happiness, and then your body’s fucked up, you get things called withdrawals, if you can’t afford that shit. And this is nothing that I feel like I – since I’m older now and I understand it a lot more – that I should be just promoting in every line. You feel me? There’s a bar in there [on “I Got the Fye”] that says, “I’m addicted to cash, these boys addicted to drugs.” And that’s not even about anybody specific. But if you feel like it’s about you? Then you might have a problem!
There’s another line about people getting “geeked on benzos” – it feels like there’s more of you observing others on drugs. Do you get what I’m saying?
Mm hmm. I’m a good observer, bruh. I like to watch people, I like to see how people think, how people react to certain shit. I’m a good observer.
It reminds me of the “Flxr” video from last year, and what I loved about that was –I loved the messaging in the graphics. That whole thing about “How do I download motivation?” and you’re like, first, “Get the fuck out of bed!” “Do your homework, meet new people, explore new things” – it might seem like no-brainer advice, but I think some people need to be told that.
Yeah. People – shit, I’m not gon’ lie, some of the messages in that video? I be needing that shit! Sometimes I be needing it. And all of those messages aren’t specifically coming from me. Those aren’t quotations from me. It’s really my editor, Stan. He’s a super, he’s motivational, you could ask him, “What’s your favorite thing about Jump Out?” and he would send you a three-paragraph essay, and break it down. That’s just the type of person he is. He loves motivating people.
Is it kind of coming from that same place of motivation in the new song “Room 156” where you say, “Bitch you won’t know if you never try to go”?
Yeah I feel like it’s the same shit, it’s the same motivational thing. But it’s all in how you take shit. I feel like all my lyrics, it’s just – how you feel about em is dependent on how you take it. Somebody might hear that line and think, “Oh this n—a just disrespected me, he just called me a bitch!” or somebody might hear that line and think, “Damn, you’re right! If I don’t try to go I would never know!” You feel me, you never know until you try it, you never know until you do it!
I mean, I’m curious if some of your fans may be in a place in their life where they don’t want to get the fuck out of bed because they feel like they have nothing to get out of bed for.
You have to make something to get out of bed for! Yo, sometimes I feel the same way. And sometimes I don’t get the fuck out of bed. But you have to make something to get out the bed. You have to make your life worth something, to get out the bed, and do something! Even if you don’t have something to do, make there something to do, make it a goal to wake up and – yo, when I make my bed up? That’s when all the plans start falling in line! All you gotta do is get up.
In “I Got the Fye” you call yourself the “big boss bully”? You don’t seem like a bully to me!
No, cause people be trying to bully me though. They be trying to bully me, so I gotta let em know I’m the bully, you feel me? If y’all wanna play the bully game, we can bully each other. I’ll be the big boss bully, It’s just me flexing, you know.
I just don’t know why, certain artists people seem to want to target for abuse. I talked to Rich Amiri about it back in December. I talked to Nett about the doubters and haters. And they often seem to happen for no good reason.
Yeah. You never know when you’ll get hit with it bruh.
But you don’t seem to be subjected to that, people seem to have a lot of good will towards you.
Nah, honestly, me – seeing everything that’s going on, I feel like I have been targeted like that. But I don’t know, they just pick and choose. But you shouldn’t feel bad about it. You should just roll with the punches and keep doing you. You can’t let em get to you, cause that’s how they break you. They’re trying to break you, that’s their whole goal. They’re trying to see if they can get a reaction out of you. They want to see if they can be the reason that Lil O quit! “Oh yeah, I texted Lil O and said this and then he deactivated! I did that!” you feel me, they want that type of shit, so you just can’t let them get to you. I feel like everybody has to go through it. There’s no point where somebody has the perfect career, where it’s like no hate, no hate, no hate.
At the end of the Well Well Well you did with Emwell [of Our Generation Music] a year ago, he had you write down negative words people had said about you, that you then smashed in a box?
Mm hmm
And one of them was “unlistenable” – which I think meant people who say they can’t understand your lyrics all the time? Is that still a thing?
Mm hmm. I don’t understand it, I feel like some people genuinely have like fucked up ears? But I hear snippets that I put out, or some shit, where I can hear the words perfectly. Everybody in the studio can hear the words perfectly, and I got fans texting me every single lyric perfectly. But then you got the vast majority of haters that’s getting like 20 thousand likes on their Twitter shit’s like, “How can y’all understand this? I can’t understand a single word he’s saying right now!” So I genuinely don’t understand. I don’t know if people are saying it just to joke, or if they genuinely can’t understand it.
I mean sometimes you want the vocals to be more up in the mix and sometimes you want em to be more buried, right?
They don’t understand that though. They’re not artists. I don’t think they would ever understand it, because as I became more and more of an artist, I started to understand.
Just to circle back, since 2024 didn’t necessarily play out because of unforeseen circumstances, exactly as you had planned – do you have a game plan all set for 2025?
I’m really trying to be on tour the whole of 2025. And just becoming him, becoming that it factor, a person everyone wants to go to, to represent their brand. So I’m gonna be working on that, my image, and really just performing hard.
I will just finish with what I said at the beginning that to see the year you just had and the setbacks – to see all the love that it seems to me you are getting from all corners. There’s no one really in your world, at your level at this moment, so hopefully you feel proud about that.
Thank you man. I am pretty proud of myself, but you know, I can always do better! I’m just striving to be greater and greater. I’m not done yet.
Photography: ANTONY RiDDLE