Jackboy — whose stage name is not to be confused with the Travis Scott-led collective — is one of the hardest-working artists out right now. Since 2019, the Haitian rapper has released six projects in total, and in 2020 alone, he delivered his impressive back-to-back-to-back albums Jackboy, Living In History, and Love Me While I’m Here. While proving his consistency with those three aforementioned projects, Jackboy has also regularly found himself linked to plenty of viral moments, from showing off rolls of toilet paper with NBA YoungBoy’s face printed on them to being the focus of Kodak Black’s ire earlier this summer.
Despite the occasional social media hijinx, however, Jackboy ultimately aims to move with respect and loyalty, and recently, fans have really been able to see a more mature side to the Floriday artist. Last winter, he opted out of copping a Richard Mille watch in favor of buying his mother a house, and in the wake of the devasting earthquake in Haiti this past August, Jackboy donated $100,000 to the cause and also teamed up with Lil Baby to build a hospital in his home country.
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Given the fact that he’s a rapper whose personality and philanthropy are just as dynamic as his artistry, it’s surprising that Jackboy hasn’t yet graced the XXL Freshman cover with all that he has accomplished. As he taps in with HNHH over Zoom for the new season of On The Come Up, he even addresses the XXL snubs, joking that he’s “already a senior.”
It’s a humble take from an artist who, at the time of the interview, was preparing to drop his latest work, Jackboy 2, but throughout our conversation, it’s clear that Jackboy has no issue grinding it out and getting his flowers in due time. During the interview, he details his steady rise in popularity, the talks that he has had with game-changing Florida artists like XXXTentacion and YNW Melly, starting 1804 Records, and what life looks like beyond Jackboy 2— including a few details about an upcoming project, for which he’s only just revealed the title.
Watch the inaugural episode of On The Come Up with Jackboy, and read the unabridged editorial version of the interview below, edited only for clarity.
Stay tuned for a new episode and a new longform interview every Wednesday.
WATCH: Jackboy’s episode of On the Come Up
HNHH: Where are you from?
Jackboy: I’m from Haiti, but I was raised in Florida.
What specific part of Florida were you raised in?
Broward County.
Take me back to your stomping grounds. What was it like growing up there?
I don’t want to say rough and tough, ’cause that’s pretty much what everybody gets, and we understand that. It was just… struggles, pretty much.
Broward County alone has a lot of big artists who’ve popped up over the past few years. Growing up, what Florida artists influenced you?
Growing up, a Florida artist that influenced me? Out of all the Florida artists was probably Plies. I would give it to somebody like Plies. I was listening to [Rick] Ross, but I could relate more to what Plies was saying. He kind of influenced me a little bit, I would say.
“I was listening to [Rick] Ross, but I could relate more to what Plies was saying. [Plies] kind of influenced me a little bit, I would say.”
From past interviews, it looks like you got into crime at an early age. I think 11 years old was your first run-in with the cops, so at what age did you actually first get into music?
I got into music at like 19. I was coming home from prison, and I got into music. That was something where I was like, “Aight, let me do this instead of what I’m doing because this ain’t working.” So I was like, “Let me try music,” and I got into that.
Do you remember your first song by chance?
My first song? Yeah. I do remember it. I hate it. [Laughs]
Walk me through your first time in a studio. What was that session like?
My first studio session was when I came home, and I was like, “What the fuck?” Like, “Damn, I sound like this?” It was just crazy for me to hear myself on a mic. It was like, “Damn. This what I sound like?” It was weird at first until I started getting more used to it.
I know what you mean. A lot of times people don’t like the sound of their voice. Is that what it was kinda like?
Yeah, I didn’t like the sound of my own voice. In my head, I was the rawest person in the world. With my first song— I didn’t like it, but I was like, “Damn, this the hardest song in the world!” But I knew I had to get my voice and delivery more on point.
How did your family react to you transitioning over to something more positive?
I feel like they loved it. That’s pretty much everybody’s goal and plan — to get legit with it, regardless of what you’re doing. Even if it’s not your family, that really should be everybody’s plan. People that’s in my family, they liked it the most and respected it, seeing what I had to go through to get to it. So, of course, they gonna love it.
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You’re a Haiti native. How are you currently feeling about everything that’s been going on with Haiti this year, from the president’s assassination to the earthquake?
Yeah, it’s real crazy right now. I don’t really know nothing about the president’s assassination. I don’t really know what’s going on too much on that topic. But as far as the earthquake, I was trying to go out there last Monday to personally pass out stuff myself— to go into shops, buy it personally, go to hospitals, give money. We setting it up. The only reason we didn’t go Monday [was that] we had a problem with the jet people, but we’re going next Monday to actually go out there and do it, you know what I’m saying? Instead of sending something over [from] here to there and I don’t know if it’s getting to the right people, I might as well go out there and hand it to the right people myself.
Many people got familiar with you through Kodak, so walk me through how you first became friends.
We first became friends just being in the same neighborhood, being around each other. And I was like, “Well, this an aight person to be a friend with,” so we became friends.
I don’t know if you saw the rumors, but when I first heard of you, I saw everywhere that you two were cousins, or that y’all were related.
Ah, yeah.
What was your reaction to those rumors?
Blood don’t make you family. Loyalty do. If it’s loyalty, we could be brothers. If you loyal to me, you my brother for real, for real. After that loyalty ain’t there…you know. Sometimes, friends might be closer than brothers, like a real-deal brother that you live in the house with. You might be closer with your friend, so it’s like, “Damn, that’s my brother too.” I don’t love my other brother no less, but I love him no less than my other brothers, like my real-real brothers. I love them the exact same, like he had come out my mom type shit. When they was saying it, I still was feeling like, “Aight,” cause the blood don’t really do it. It’s the loyalty. If the loyalty is there, then that’s what it is.
I noticed that your singles this year don’t have Sniper Gang on them. Did you sign a new deal?
Nah, it’s not that type of situation. I’m building my own label up, 1804 Records. I was kind of already done with Sniper Gang [and] the obligations I had to fill, but the world just didn’t know that. I just kept on repping throughout whatever because that was my brother label. We gon’ get this shit big as fuck, regardless. I just ain’t never come out and say, “Oh, I’m this-this, or this-this.” At this point, I feel like I’m just gonna build up my label. I already filled everything all the requirements I had to do for Sniper Gang. I owed one album. I turned in three. I gave three albums.
“I was kind of already done with Sniper Gang [and] the obligations I had to fill, but the world just didn’t know that. I just kept on repping throughout whatever because that was my brother [Kodak Black’s] label.”
Can you tell me more about 1804 Records? Tell me about the inspiration behind the name.
1804, I got that tattooed on my face. That’s the year Haiti signed for its independence. I wanted to bring my Haitian culture into this music I got going. Imma do the label like that— start signing artists, cameramen, producers, and just build it up and see what it can do.
WATCH: Jackboy “Where I’m From” music video
Coming up in Florida, like how we discussed, there’s a massive group of artists that came out of Broward County specifically. I’m assuming that you’ve likely met or talked to people like XXX or Melly, so what do you have to say in general about Florida’s hip hop scene?
Florida’s hip hop scene— I rock with it, I like where it’s going. Then people like Melly, people like X, they real different from regular Florida artists you see everyday. People like X is the reason I want to switch up my flow. We got a whole other sound in Florida that motherfuckers not tapping into. Nah, let’s get this bag. X is really the one that influenced a lot of my new sound. You from where I’m from, and you sound like this? You know what—let me get comfortable in there too, and open up and try more new things.
“People like [XXXTentacion] is the reason I want to switch up my flow. We got a whole other sound in Florida that motherfuckers not tapping into. Nah, let’s get this bag. X is really the one that influenced a lot of my new sound.”
Watching the No Jumper interview, I noticed that X reached out to you while you were in jail. Tell me about your relationship with him and what advice he may have given you.
I rock with X heavy because every single time we talked — and I talked to him a couple times, a lot — he reached out to me. Throughout that whole time, he was already a superstar. He was already bigger than me, so for you to come back and just steady do that, I super respect it. I’m in jail. He’s hitting me up, “Aye, bro. What’s your inmate number so I can send you money?” Then he’s sending me the money. Stuff like that was like damn, what the hell? I met him, and then he was like, “Hey man, come to the studio.” He’s trying to force me to get in the studio, and I’m just like, “Nah, man, I’m on lean”— stupid!
I’m not understanding what it was because I was thinking we’re here forever. So I’m not understanding that this shit important. Even though we didn’t get the song, I still respect [him] super heavy like we got it, like we was in there. This man was hitting me up. He did not have to. I wasn’t really trying to be a rapper at that time, and he seen it, so he was trying to be like, “Aye man.” He would stay stuff, but I was like, “Nah!” At the time, the music wasn’t putting no money in my pocket, so it [didn’t feel] worth it, like “Whatever, I’ll do it later. I’ll get to it.” I always had that mentality, but really, it’s like we gotta be getting to it right now.
I know you said y’all didn’t end up finishing a song or anything, but did you ever get to the studio with him at all?
I ain’t get to the studio with him, but I sent him shit. And I think I could still get a X song, but I’m not really pressed for it. I fuck with him, and it’s deeper than that. I wouldn’t even want it certain ways. Say right now, if we had a song, if we were to record it— I would’ve tried to find a way for everything to go to his son or some sh*t, every dime. Then I would try to find a way to do it instead of just, “Aight, let me drop this, and juice up real fast!” Nah. I would have to finesse it another way so it could make sense. I respect [him].
Also in that interview, I saw that you and YNW Melly have a unique connection through 100K Track. Speak on your relationship with YNW Melly.
I rock with him because I can tell he’s different, and he doesn’t really care about being different from Florida artists, but you still street like us. You still with it. I fuck with Melly. Our relationship, it’s pretty much been through the phone because when he was on the streets, I was locked up and talked to him. Then he blew up, and [when] I came home, he was locked up. It was always through the phone, but I rock with him. We’ve got a song together, and it’s some hard, hard, hard shit. He a real one. With his situation, our county is crazy, so hopefully, he makes it through that. He’s locked up in Broward right now, but I rock with him. He a cool one.
“I fuck with [YNW] Melly. Our relationship, it’s pretty much been through the phone because when he was on the streets, I was locked up and talked to him. Then he blew up, and [when] I came home, he was locked up.”
With the song that y’all have together, is it something that fans can expect from you soon or are you holding it off?
I’m not sure because it’s his song. It will come whenever he feels like dropping it. It’s his song. I just did the feature, but it’s hard.
In addition to working with Melly, what other popular Florida rappers are you still trying to lock in a song with?
At this point, I think I did songs with every Florida rapper that I wanted. I did a song with Rick Ross. I did a song with Plies. It’s like, who else do I go to in Florida? I don’t know. It’s a lot of hard workers in Florida. At this point, I don’t even feel like I want a song with people. I want to work hard enough so people want a song with me. I ain’t gonna turn them down. I ain’t gonna be on my high horse like “Oh nah, nigga!” But come ask me for it. Imma keep on dropping till you like, “Aight, I just need a Jackboy song right now!” That’s how I want to do it right now. I want them to come work with me and come ask me. As far as artists in Florida, I don’t got one that I’m like, “I need them on a song right now,” but all of them hard. They’ll do justice to the song, but I ain’t really [looking for that] right now.
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Speaking of dropping, last year, you went on a complete rampage, and you dropped three projects within a span of nine months. What inspired that crazy run last year?
Just me wanting to drop, and then it was more pressure last year because I was out here by myself like, “You gotta hold it down.” Then you got to be making this money. This money ain’t gonna be given! So you’ve got to grind, grind, grind, and make it look good, make the whole gang look good. That’s pretty much what it was— just me trying to make the whole gang look good and hold it down. It was helping me out too. It was making me bigger too, putting me in a position like that, like “Damn, you got people depending on you right now.” It created another work ethic, a different type of hustle in me, so that helped me out too.
How did releasing those three projects back to back change people’s perspective on you?
It changed their perspective because people were seeing, “Damn, this kid willing to work.” Then they actually heard improvement, so it was like, “Damn, he gon’ go out and get it! He gon’ hustle,” so I feel like they needed to see that right quick, just that grind. It made them respect me more as an artist for real, for real. I got a lot of fans right now that respect me. That makes me wanna go even harder.
A lot of times, we’re introduced to people through co-signs from artists that we already like, and it’s kind of shoved in our faces. But with your projects last year, you definitely proved that you’re your own type of artist.
Preciate it.
Out of all three that you released last year, which is your favorite?
Jackboy. I ain’t gonna lie, I feel like all of them got better. I feel like Living In History, Love Me While I’m Here, all of them that I dropped got better than the one before. I feel like all my projects get better, but that Jackboy project did something different to my life. I’ve got to respect that project right there. That shit did something different. That was it. I needed that on my catalog. If that wouldn’t have been on my lil catalog, I wouldn’t be here right now. That one did it and set up the plays for Love Me While I’m Here and all the other ones.
Moving on from last year, you did the XXL freshmen pitch. But now, this marks two years in a row that you haven’t made the cover. How are you feeling about that?
Hey, I’m already a senior. [Laughs] But nah, I ain’t tripping. I like it — it’s a little competition. Even the freshmen you’ve got, I might be doing way more in life than them, so that don’t really make who’s a winner and who’s not. But now, y’all got me wanting to win this shit! I don’t care if it’s 5 years. I’m coming to get this. Then, when I get it — man, stop playing with me! But it’s not something [where] I’m [like], “Oh my gosh, I need XXL, it’s gonna make or break me.” No, it’s not. Your work ethic is what’s gonna make or break you. There was people that was on the magazine cover 3 years [ago], and they still got to send me them invoices for them features. They still got to send me them backends and frontends. It don’t matter ‘cause you were on the XXL cover. It’s still people grinding out here.
I still salute them, even with the people they pick. The world might be like, “Oh, that was a horrible pick.” I might feel like that too, but shit, if I was picked, some people might feel like, “Hey, Jack is a horrible pick!” I ain’t tripping. Grind. Do what you do. But as far as the pitches, Imma start getting a little jazzier with ‘em. I might come in smoking a cigar on the next one ’cause I’m becoming a senior. What are we doing this year? Is it this year or next year? Let me know! Do I gotta drop more albums? How much y’all want this year? I ain’t got time to play and answer the most wonderful questions the perfect way. Listen, is we doing it this year or not? I’m still in that contest. I still want it just because they want to be cute about it. Now Imma come grab it.
What do you think about this year’s list?
It’s cool. They got some hard people up there. They got Dugg up there. They got Shiesty up there. That’s hard.
Were there any artists that you feel deserved a spot, in addition to you of course?
You don’t want me to start naming artists. It’s too much people doing their thing out here. It’s people that I don’t even converse with, that I don’t even follow, that I don’t even talk to. But I feel like, “I ain’t gon’ lie, lil bruh doing his thing.” At the end of the day, it is what it is. I feel like even the people that should be doing that, they still doing great in life right now, without the cover. They doing better than some people that’s on the cover.
Speaking of doing great without the cover, you capped off a huge year last year by buying your mama a house. You said you were originally gonna buy her a Richard Mille first, so what changed your mind?
We can’t live in a Richard Mille. I wanted to live inside of it. If we could’ve lived inside of that motherf*cker, I would’ve grabbed the Richie. You just can’t live inside of it– but they didn’t think of that part yet. They’ve got to make a new watch that you can live inside [of]. But nah, you’ve got to be smart. Could you live in a Richie? No. But could you live in this house, and have it forever, and maybe just pay $8,000 in taxes a year–little stuff– but you ain’t paying nothing, you just pay property tax? That’s cooler. That’s more fly.
I peeped that you still appreciate some good jewelry though. I saw on Twitter that you recently paid Johnny Dang a visit. Who are your favorite jewelers in the game right now?
Right now, Johnny Dang and Stacks Customs, my favorite jewelers. Stacks Customs, he’s a local jeweler where I’m at. He be looking out for me, and Johnny, he’s just, “Hello!” Next level. With the jewelry I get, I spend a lot on it, but I still try to manage it. I still try to work through features. I still try to grind and go get shit instead of trying to rip it all the time. Right now, I could still buy a Richie, but is it worth it right now? Nah, let’s do some features, and that’s how we’re gonna pay for the Richie.
In addition to buying your mom a house, what else have you been doing to build generational wealth for your family?
Right now, my mom takes some of my money, takes it to Haiti, and builds little stuff, but I’m really trying to start down here. I ain’t really get into it, into it. I’m really trying to start down here, but at first, I’m gonna start with my label. That’s why I’m starting 1804 Records, so I can build more money off the music, which I know is gonna work, and then tap into other stuff. We’ve got to real-deal build it off of the music. Imma use the music as the platform to get into everything else. I want to do rental cars. I want to start a rental car company. I wanna start car washes where I’m at, but I want to start the ones with the free vacuums that’s all day, not the ones where people wash personally. I want all that, but right now, Imma make the music to the point where I can still live comfortable like this, and do all that at the same time. I feel I got to sign a producer for me, a beat maker — Imma always want to make music — and I got to sign a couple [of] artists, and we just grind.
Let’s talk about Jackboy 2. Tell me what inspired you to revisit your self-titled project from last year.
That project was the opener. I always wanted to do a “2.” I was already planning that, so I felt like this was the best time to do it, especially [because with] the things I’m talking about in the music now, I feel like I’m giving Jackboy. I’m giving you me, so this title was perfect, Jackboy 2. I’m giving the same vibes as the first one. I’m already done with the next one for real, for real. At least halfway done. I’m on the next one.
Are you experimenting with any more sounds on Jackboy 2?
Definitely. I’m using my voice, but from the first Jackboy to this Jackboy [2], I’m more comfortable with it. With the first Jackboy, I was using my voice. This time, it’s like, “Hold on, he been in there for a little minute.” I’m more comfortable with it, but I always use my voice because I feel like that’s what’s making me different from Florida artists. How I approach the beat. I want to keep that unique style about me, [for people to say], “I noticed Jackboy on the song,” or you can hear any song, and it’s like, “Oh yeah, that’s Jack right there.” I want it to be like that.
You have the video out for “You Can Go”. You were in Paris for that, right?
Yeah, I was in Paris.
WATCH: Jackboy’s “You Can Go (Na Na Na)” music video
What was that experience like, filming the video there?
The experience in Paris was next-level different. It’s super fly. I like it. I want to go back to Paris for real, for real. That’s where all the fashion started, and I’m big on fashion, so I was in every store. I was loving it. It’s just a good vibe, especially being by the Eiffel Tower and all that.
Did you go in the Cartier store? Were you on the Champs-Élysées with all the expensive luxury stores?
Yeah, for sure. I went in the Dior store, Celine, stuff like that. That sh*t is different. The food, it’s just… ahhh. Everything else is it.
You’re back on tour with Tee Grizzley in October. How are you feeling going into the “Built For Whatever” tour?
I’m excited about it. Me and Tee Grizzley, we got a whole different type of relationship than me and any other rapper. We’ve been around each other so much, and we probably went to the studio with each other one time. I’ve seen him like 3 times, and all 3 times, we’ve played chess. The one time we went to the studio, it was like, “Oh yeah, I vibe with you. You just want to play chess all day, and that’s what I want to do.” You’re challenging somebody playing chess, challenging their mind. I like that. I rock with Tee. Me and him on tour, I know it’s gonna be lit. It’s gonna be turnt. And it’s opening me up to a whole new fan base too. He’s letting me tap into his fan base, so I respect it.
What cities are you most excited to hit up?
I’m not even sure. I’ve been on the road before and experienced cities, but I’m not sure. I’ve got to witness it all again, so [for] my next trip, when I go on my tour, I can know which cities. I’m just ready to get out there. We’ve been in COVID and quarantining, and I’m ready to just rock. I’m ready to see every city.
You were probably ready to go on tour last year before everything happened.
I was still doing shows through the whole thing. [Laughs]
Before you go, I’ve got to understand the story behind this NBA Youngboy toilet paper.
That wasn’t nothing. I ain’t even think of that. I was just riding for the gang, you know how you’re supposed to do. Say you’re my homeboy, and you’re going through it with somebody. I don’t know what the problem is about, and I’m not trying to see what the problem is about. I’m just ready to real-deal ride with you. That’s why I want my homeboys, if they get in a situation, to make sure it’s something real-deal important, because I real-deal be passionate about certain situations. But it ain’t nothing. It’s good.
I ain’t gon’ lie. When I feel like somebody’s disrespecting me, I know how to make people mad. I will make somebody mad, then Imma stand on it. You know you do the little petty stuff to get somebody [tight], and it’s to really provoke you to come at me? It’s like bait. But that wasn’t about nothing. It was just me, riding for the gang.
Did y’all actually sell it?
I don’t even know what they did with it. I was just riding for gang.
Somebody that you’ve worked with in the past is currently dealing with a situation– that’s Casanova. Do you have anything to say about his situation? And have you communicated with him recently?
I definitely haven’t communicated with him since he’s been locked up. To speak on him though, I feel like Casanova is probably one of the realest rappers out, but I see what he be posting. I’m like, “Damn, whoever he’s speaking on, that’s kind of messed up.” Because I’ve seen, when I was in New York, that he took care of everybody around him. He even took care of me when I was out there, making sure I’m alright. I’ve got hella respect for Casanova, but his situation, I hope he makes it out of that too. He’s definitely a real one. Some rappers play off hood politics like, “Oh, this rapper don’t like this rapper.” Casanova’s not moving like that. That’s just what it is. Casanova, he’s the type to stop the beef. He’s that type of guy. I rock with Casanova. I respect him.
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Looking to the future, is there anything else we can expect from you in 2021, in addition to Jackboy 2?
In 2021, for sure. Imma have a new project I want to drop in 2022, but I don’t know if I should throw the name out there…But Imma drop a new project in 2021. I want to call it It’s Okay To Not Be Okay, and then I want to just keep on coming. That one’s already kind of done. I want to stay on ’em how I was last year. Imma get back in that mode.
“Imma drop a new project in 2021. I want to call it “It’s Okay To Not Be Okay,” and then I want to just keep on coming. That one’s already kind of done.”
Where do you see yourself going in 5 years?
I don’t even know because at first, I used to dream about it, like “Damn, [Imma get] a big ass house!” But with the stuff I’ve got now, this is all I’ve been dreaming about [these last] 5 years, so now that messed me up. It’s like, “Damn, what could I be in 5 years, now?” I don’t even want to put no limit on it. I don’t even want to manifest no “Oh, I’ve got 5 Lamborghinis.” No, I want 30 Lamborghinis. Wherever we at in 5 years, that’s where we at. I just want to be as big as possible. I want to reach my full potential. But I don’t really want to have my mindset, like “Aight, this is what I need.” Nah, let’s get huge. I feel like I should have my label running in 5 years. I feel like my other businesses– the next time you come with that question, I need to have some restaurants and all that in 5 years. I don’t know how far my success is gonna be. Whatever it gets to, we grinding.