Jimmy October’s Defines the Sound of his Generation with New Calypso

In a packed Silver Spring, Maryland venue last September, Jimmy October was blanketed by a sea of roaring reception. Performing a solo set while in town as an act on Kes the Band’s Liki Tiki tour, the artist describes the audience’s reactions to his music and presence as an act of affirmation. “There was just so much love. So much people screaming, people coming up to me after like, ‘Yo, I’ve been waiting for you to come to the States. For me, that was one of those nights where it was like, ‘Okay, this makes sense,’” he says with confidence.

This refers to his career and the artist, hailing from East Trinidad, is continuing to push the sonic boundaries of music that can be produced from the Caribbean. Through his own sound, what he’s coined as New Calypso—the fusion of sounds from his native, like soca and calypso, with other Afro-diasporic genres—he is on a mission to architect new artistic frontiers for artists to create music towards. Though the biggest difference between now and the earlier stages of his artistry is that he’s no longer waiting for permission to contour sounds in the way he sees fit. Says the artist, “I want to find ways to discover what amapiano and soca sound like together, like with ‘Healing’ — let me get that challenge.”

Jimmy October drinking a glass of rum
Jimmy October standing drinking a glass of rum

Conquering that feat isn’t done independently. In fact, producer and frequent collaborator, Tano, has been instrumental in carving a landscape for the artist that ensures his New Calypso sound is generative, inventive and fresh. Much of the work that allows them to get there is driven by cultivating a familiar sensory experience for their listeners. “Tano is somebody who would be like, ‘Yo, you heard this?’ or, ‘You remember this?’ and we would play old records or we would play songs from the 2000s,” he says describing an aspect of their creative process.

Lately, Jimmy has been really inspired by tapping into that feeling of nostalgia. During the early to mid-2000s, Caribbean artists made significant waves within mainstream music through records like Beenie Man and Mya’s 2000 “Girls Dem Sugar,” another banger Beenie Man hit featuring Janet Jackson in 2002 titled “Feel It Boy” in addition to the multiple records Sean Paul released that gripped screens and airwaves alike. Recreating those same feelings, of being seen and heard through music, is what’s driving his production. He shares, “I grew up in that time, and it’s important [because that’s] when I began really falling in love with music. There’s a feeling attached to those songs when I listen to them. I tried to tap into that feeling and ‘Rum & Calypso’ was the beginning of that.”

The newly released record produced by Tano and another one of his collaborators, Brooklyn Decent, is an infectiously groovy single that melds the stylings soca, dancehall, afrobeats, R&B and, of course, calypso. It’s of no surprise that considering the lyrics and its title, Jimmy was inspired by a fete. He shares its origins: 

“Tano and I were driving around and the chorus came [to us] in the car after or right before a fete, to be honest. Just because, and I say this, even with ‘Remember the Days,’ a lot of times there are different things that inspire [my] songs. Sometimes the energy of a moment inspires me to write. It doesn’t necessarily have to pertain to me, it might just be a vibe that I feel.”

With his new single, Jimmy pays homage to the storytelling element of calypso, but modernizes it so that it maintains the ethos of New Calypso. He shares, “I described [the record] as a new age type of storytelling because the chorus is ‘This pretty gyal wah rum and calypso/ Fly to me lemme show you how di ting go.’ If it was slowed down, it would actually sound like a calypsonian telling you about a girl who wants something and she needs to come here to get it, but because [the record] is fast, it’s gonna make you bounce. It’s me trying to tell a story about somebody, and even the idea of that is a very old concept inspired by calypso, but I’m just trying to find a way to make it sound like 2023.”

Listen to Jimmy October’s “Rum & Calypso.”

The Ultimate Guide to Antigua Carnival

Our highly-anticipated 2024 Ultimate Guide to Antigua Carnival is here! Lock in those flights and stays, for a fete-filled time…
The Ultimate Guide to Jamaica Carnival

The Ultimate Guide to Jamaica Carnival

Our highly-anticipated 2024 Ultimate Guide to Jamaica Carnival is here! Lock in those flights and stays, for a fete-filled time…
Mas in Miami Is Unlike Anything Else

Mas in Miami Is Unlike Anything Else

A few weeks ago, masqueraders took to the streets of Miami for a colourful celebration of Caribbean culture
The Ultimate Guide to Sugar Mas (St. Kitts & Nevis Carnival)

The Ultimate Guide to Sugar Mas (St. Kitts & Nevis Carnival)

Experience the sweetness of St. Kitts & Nevis during Sugar Mas, which combines the festivities of Christmas with the pageantry…
The Ultimate Guide to Saving For Carnival

The Ultimate Guide to Saving For Carnival

With our guide, discover how you can chase carnivals without breaking the bank and by saving up your coins for…
Scroll to Top