Kalpee Talks Island Wave And Underrepresentation Of Caribbean Music

In Trinidad, Kalpee was starved of creative resources and worn down by cultural expectations. Beyond the island’s shores, he felt the strain of underrepresentation. In response, he co-founded Island Wave, a platform built by and for Caribbean artists who are tired of enduring the same. 

On 18 March 2022, a vibrant cast of musicians shared the stage in the Flamingo Cantina at SXSW, a globally-renowned music festival. The room pulsed with Reggae, soca, R&B, calypso, and Dancehall. The crowd was animated, with some spectators waving national flags through the air. The host, Ras Kwame, kept the energy flowing between acts.

That night, the Island Wave stage became the first Caribbean show to physically debut at the Austin, Texas-based festival.

“The place was ram,” Kalpee recalled on a call with DancehallMag. Some fans came for Jamaican rising stars Jaz Elise and Tessellated. Others came for Freetown Collective, Nailah Blackman, Jimmy October, and Kalpee – the self-described “New Calypso” artists who inject Trinidad and Tobago’s homegrown music with greater thematic depth and broader influences. No matter the initial draw, people showed up.

Kalpee credits collaboration and harmony for the success. “It was special because it was seamless. People complemented each other. Whenever someone came on stage, it was a new angle, a new element of Caribbean vibes,” he said.

The Trinidadian native goes full throttle at the beginning of our conversation, zigzagging between topics as he works to string together the essential bullet points. “I think I drifted away from your question, sorry,” he admitted at one point. It’s no problem, I assure him. In juggling Island Wave’s operation with his own solo career, there’s surely a lot to cover.

Per Island Wave’s website, one of the platform’s main focuses is to “secure performance opportunities and funding to power the stage to help bridge the gap between international music markets and the Caribbean diaspora.” One major hurdle in getting Caribbean artists on foreign stages, however, is the fact that many need to be issued work permits or travel visas first. And it takes a certain level of stamina to endure the grinding realities that have come to define the approval process.

“I just don’t understand how it’s so difficult to get a visa as a Caribbean person,” Kalpee says. “To go to the U.S. and perform is nearly impossible. You almost need to prove years of work booked in advance to even be able to apply. And how do you do that if you can’t get a visa in the first place?” Fortunately, he adds, several artists on this year’s Island Wave stage worked together and leveraged connections to relieve at least some of the travel-related stress.

As we speak, he’s gearing up for a show at The Peppermint Club in Los Angeles, followed by a late-September trek to Singapore for Music Matters Festival — an event similar to SXSW, he explains. Due to funding restrictions, Kalpee might end up being the only artist representing the platform at this year’s festival, though he tells me that the main focus is to lay the foundation for next year’s appearance. He envisions Island Wave’s line-up boasting six or seven artists, minimum.

At the heart of Island Wave’s mission is the desire to bring Caribbean music to the world, an ambition that stretches beyond the stage. One of the platform’s other initiatives is to furnish Caribbean communities with better-equipped recording studios. “For someone to be able to create the best quality of anything, that person needs the right tools,” Kalpee tells me. As it stands, Trinidad and Tobago, like many other developing nations, lack these resources. 

He believes that remedying this fact will ripple through other industries like tourism. “I want to see the top of everything and for Trinidad to have some amazing studios on the coast so that people can say I wanna go there to write my next album. We should have the infrastructure to host professional artists from all over the place.”

That Kalpee sees music as a potential balm for society’s troubles can be explained, at least partially, by the fact that his life is rooted in the art form. Born Christian Kalpee, he began performing at age six, often singing calypso in competitions. He later learned to play the steelpan and bass steelpan while in school and spent several of his teenage years singing with the soca band, The Entourage.

As he leaned heavier into his solo career around 2017, he shifted away from traditional soca and calypso, opting instead to fuse Trinidad’s native sounds with the genres that moved him – namely, trap, rock, R&B, and Dancehall. Songs like Island Gyal represent this fusion, with soulful melodies gliding over steelpan flourishes.

He credits his move to Los Angeles with helping to liberate his sound. “When you leave home you notice all the random things that are just ingrained in us. But now there are no limitations. I’m deliberately experimenting all the time to try and find that nice blend of genres that really complement each other,” he says.“This environment calls for you to be anything you want.”

Feel Good Playlist, Vol. 1, the second of Kalpee’s lockdown-era EPs, testifies to this newfound freedom. Its tracks evolved as he jetted between Trinidad, the U.S., and Barbados. After finding himself stuck in England due to pandemic-fuelled travel restrictions, he familiarised himself with the production software Ableton and set out on finishing the project. Bearing features from Stefflon Don and Freetown Collective, the EP distils the progressive ethos of the New Calypso movement into a lean, five-song package.

This blending of genres has also laid bare several flaws in how digital streaming platforms categorise and market music. Caribbean artists are often required to list their music as Reggae – whether or not it is – before they’re allowed to choose ‘Caribbean’ as a sub-genre. On other platforms, Kalpee has been left to select between Reggae or pop, for lack of a better option. “It’s something that we’ve been challenging,” he says.

That quest for visibility and inclusion is what ignited Island Wave’s mission in the first place. In 2020, Kalpee found himself and Tessellated co-billed among Russian artists at his first official SXSW performance. The lack of cohesion on that roster opened his eyes to the need for his West Indian brethren to unite.

“If I’m on the Russian stage, I’m not necessarily going to find those fans who like Caribbean music. But if Tessellated, Sevana, Jimmy October, and I are all on the same stage, there’s a good chance that other people’s music resonates because it’s all Caribbean music at the end of the day,” he explained. 

The festival organisers were receptive to this logic and Kalpee, along with his management team at FVP Global, went off pitching and planning. These joint efforts bore fruit in 2021 after SXSW debuted its first-ever Caribbean-exclusive roster on what was then called The Island Stage. Kalpee flew from Trinidad to Jamaica for the virtual performance, which was staged in Kingston. There, he co-hosted alongside Kadiyah McDonald and performed to close out the show following sets by Sevana, Tessellated, Mortimer, and Khalia.

The virtual 2021 SXSW show ranked among the top five most-watched shows of the festival. Reflecting on what led to that, Kalpee noted, “this is a movement with different emerging artists, quality ones, positive ones. From my knowledge of SXSW, separate artists come, go to the stage, do their thing and then leave. The artists performing on the Island Wave stage all went through the same challenging process of getting this together. For 2022’s performance, we even rehearsed with the same bands and travelled together.”

Following the platform’s recent success at SXSW, Island Wave is currently adding another arm to its operation: that of a record label. Like all of Island Wave’s efforts, this move is driven by collaboration and fuelled by a desire for positive change. “We’re trying to put more energy into the islands. I often speak more for Trinidad than anywhere else ‘cause that’s my home,” Kalpee says.

“We can’t just rely on oil and gas. We have to put knowledge and resources into the arts and into creativity so that it inspires people through generations. That’s where this all comes from at the end of the day.”