Get to Know Trinidad’s Jimmy October and His ‘New Calypso’ Sound

Words by Maj Johnson
Photos by Olajuwon Scott

At age 23, Trinidad’s Jimmy October has already undergone a creative self-reinvention, refining his artistry to create his own lane. Having gained his first dose of local popularity as a rapper several years back, October is currently exploring his identity through a style he’s dubbed “New Calypso” —  a nostalgic but modern celebration of Caribbean heritage and sounds, mixed with R&B and Afropop, first unveiled on last year’s Vacation EP. “I just want to make music where you think: This is what music from Trinidad should sound like,” October says of the new direction.

This week, the Sangre Grande, Trinidad native unveils “Remember the Days,” his first release since joining Protoje’s In.Digg.Nation Collective. Accompanying the single (which is out Friday via the In.Digg.Nation Collective label and Delicious Vinyl Island) is a video that further elaborates his vision in its depiction of classic Caribbean style. A jack of all trades, October contributes visual direction to all of his projects.

On a recent Saturday, I welcomed Jimmy and his assistant to my home in Trinidad to discuss his past and future plans. Our conversation scratched the surface of the artist’s motivations, creative philosophies and commitment to challenging social norms.

Where did the name Jimmy October come from?

A couple things. The first influential hip-hop album for me was College Dropout. [Kanye] has a skit on the album called “Lil Jimmy.” In 8 Mile, Eminem plays Jimmy, his real name is Jimmy. At that point in time, I used to do more rap. When I saw 8 Mile, I was like Em was a real regular person and lives in a trailer but he had this super power, which was his talent. And, well, I was born in October.

How would you describe your sound now?

There are things I like about hip-hop and R&B and, not just how it sounds, but how down to earth it is. But also I feel like there are so many cool things about our culture — Trini, and Caribbean by extension — that we don’t usually tap into. I get Carnival but I feel like there are other things that don’t get highlighted. Musical instruments like steelpan shouldn’t just be for Carnival. I want to find a way to make that blend with my R&B, whether that be melodies or things that I might choose to sing about [but] that you might not want to sing about while you on the road. I’m trying to find that balance. So when it comes to the sound right now, my producer and I, Tano, came up with something we call New Calypso. I was super afraid of going into that because I don’t want to seem like I don’t find old calypso cool or that I don’t have respect for it. But that’s what I’m creating right now in terms of the Vacation EP and the next few songs.

What were your influences growing up, from your childhood, that you internalized that you see coming out now?

Definitely Kanye West, Michael Jackson, Bob Marley “Satisfy My Soul.” It’s the way that song feels that I try to get out. Machel Montano, for sure. Heavy influences. Apart from music, Kanye West is my biggest creative influence, because I think I can relate. I remember hearing about Kanye going to the label and people being like “Nah, you not going to be a rapper” and then a few years later, we see someone who believed in himself, no matter what people told him. Sometimes I think about when I first started music here and people would say, “Oh, yuh don’t do soca.” It would be really easy for me to be like, “They said I don’t make soca so I guess I’m not going to make music.” People underestimate how easy it is, if 100 people tell you that you can’t make music, to think, “Oh well I guess I’m not going to make music”

Why did you continue to pursue music then?

Why not? I always say, some friends don’t like when I say it, I think the only thing I’m good at is music. And, by extension, I’m good at creating things and building a whole world around whatever project I’m working on.

When did you first start making music?

Me and Nicholas Subero, that’s my childhood best friend and the other founder of my collective, Overdose, had a group called Sagitarius. He was born in December. That’s the first person I started writing music and singing with. It was R&B. We really liked Usher and I don’t think anybody else at that point in time. Usher was the first person I was a huge fan of. I think he’s still a G but they fight him so much. He’s still a G, though.

When did you feel you wanted to shift your creative direction as an artist from rapping to New Calypso…

Because I started doing R&B, it was always at the back of my mind: “Oh, you don’t do soca…”.  As much as I believe in myself, it’s not like I didn’t think, “Oh, this might not work.” Me and [rapper Jay] Nahge did a project called [Something to Believe In] and I really enjoyed making it. It’s five songs and an intro. There was one producer, which made it easy as well and we spent a huge amount of time together around that time, bouncing ideas off each other. I think I was a little angry so I feel like there were things I just wanted to put out. I would have known [producer] Tano from before. I think we went [to] a party together, and he was like, “I have this idea for you of a more island vibe.” He had a way that he challenged me, like “I have island songs.” And I was like, “Don’t play me any beats that you think Drake would sound good on, or Justin Bieber.” Let me hear you find your own sound. Don’t bring it to me cause you think it’s popping right now. “Controlla” and those songs are so much fire, but I don’t want to sound like I’m copying Drake. He sent me the beat for “Vacation,” months passed, and then one day I was like, “I’m gonna write on this.” The hook came early and as soon as I had the hook, I knew from then like, “Yeah.”

It was more of a kind of responsibility too, that New Calypso thing. I think as an artist you take up a responsibility where you’re trying to push a particular type of music or feeling. It becomes this big thing to you where you’re like, “They have to hear this, they have to hear what New Calypso is and understand it.” And I think that’s why I stopped rapping so much.

How did your collab with Steve Aoki and Bad Royale come about?

Versatility is super important to me. I don’t want to get bored of myself. I just want to make music. I don’t want to feel like I have to do this in particular. So there were definitely times where I thought I want to do some EDM. And I’ve been working with Bad Royale. We’ve always connected when they’re here. They tour, and they played a song I was on. I remember Kevin from Bad Royale calling saying Steve Aoki heard this song and was like “Whose voice was that?” And they were like, “This guy from Trinidad.” He has no idea what I look like or if I was 10 years old. He knew nothing about me. I woke up one day and saw a text, like “Hey, this is Steve Aoki, can we lay down some tracks?” Crazy. I know Steve Aoki in general because he did some work with Kid Cudi. If we talk about style and building self confidence, Kid Cudi has a big part to do with that for me. His music was just super vulnerable. For me that was the big thing working with Steve Aoki. I get to shake the man hand who shake Kid Cudi’s hand [laughs]. We got to perform together, in Trinidad here.

How did you link with Protoje and Indiggnation?

It’s a partnership, and we’ve been talking for a few years. When I put out Vacation, he DMed me like Yo, the art direction and everything is crazy. I think artists see other artists who don’t generally have a budget do something cool, and that pulls your attention. It was just a regular thing, you follow people on Instagram and see their work. He came to Trinidad, and we got to talk music more. I was playing some stuff on my phone and he was like, “Yeah it sounds good.” He went back to Jamaica and when I was finishing up “Remember the Days,” I sent it to him and he was like “Yo, we need to talk.” This was about two months ago. He said, “Let’s partner up and see how we can distribute this and find a connection.” He does reggae and I do my thing so how are we gonna find common ground to get this to work? I had to shoot the visual. It’s a super cool arrangement and that’s my G.

What can you tell us about your new track, “Remember the Days”?

Even when I was doing rap, people were like: “You have to do soca.” I always found myself in things that involve[d] soca or Carnival. I opened for Machel Monday twice [doing] spoken word. And the challenge was: How do I actually give something to it? I’m friends with soca artists. Me and GBM Nutron have been talking back and forth for a while. I wanted to make music with him. I was like I have this song I’m going to send you, and he recorded it in two days.

I definitely don’t want to be coined as the person who’s like “I want to make new soca.” I just want to make music where you think: This is what music from Trinidad should sound like. Nutron had a song called “Calypso.” I’m pretty sure people don’t even know why they like that song. It probably just has an 808, it does not have a kick drum. There’s not much music around it. I kept asking him, “How did you get people to like this song?” The BPM is kind of slow, and I thought that was genius. And that’s why I really wanted to work with him. On the EP [“First Time” with GBM Nutron] felt closer to soca than anything else.

Working with my producer Tano [on “Remember the Days”] I was like, “I want something that sounds like ‘Vacation.’” And he was like, “Stop chasing your last single.” And I had to be like, I don’t want the same sound, I want the feeling. Artists suffer from that thinking: This song was dope and it did well and I want that back. I wanted to find the feeling of “Satisfy My Soul” by Bob Marley, or David Rudder. When I put on those songs, how do I feel? And now I have my own point of reference which is Vacation. It came right after a whole lot of rap, and a dark journey, like Where did all this color come from? What gave me the confidence is that I thought it was a real good song. In my brain I was thinking, “What if Machel and Partynextdoor did a song together, what would it sound like?” I changed it after to suit. Because I really want to find a balance between what our stuff sounds like here [in Trinidad], and what I think the song should sound like in general.

How do you want people to feel when they hear your music?

Like they can’t class it. Like they don’t know. You can’t say its soca, dancehall. It’s not really pop. That’s how I want you to feel. Actually, I just want you to be able to relate. I don’t always want listeners to feel good. “Remember The Days” feels happy but it’s a sad song to a point, because it’s based on nostalgia. Nostalgia doesn’t always make you feel sad. For example, you probably sad a person is gone but you’re also happy because you can look back, and be thankful it happened.