If you’ve never heard of College Boy Jesse, you’re about to be amazed by what’s happening with this young, Trinidad and Tobago artiste who gave the world, ‘Tipsy’ in 2015. A recent trip to the United Kingdom where he opened for Bunji Garlin and Fay-Ann Lyons, may have been icing on an already sweet cake for the artiste; now added to this, we’ve learnt that Jesse’s even taken on the reggae genre.
Jesse Stewart- aka College Boy Jesse’s on a mission to make music matter.
Collegeboy Jesse has amassed a pretty loyal support system on the underground soca circuit in the Caribbean. In recent weeks he’s performed for crowds in Atlanta, New York and just two weeks ago, he hopped over to London where he opened for VP recording artistes, Bunji Garlin and Fay Ann at an event called, Face Off. “Performing for crowds that aren’t limited to West Indians has a way of opening our eyes to the possibilities- endless possibilities for not just those of us who make it to those stages, but others who are coming up in the industry,” he said.
In the past few weeks, Jesse who works closely with T&T based production house, ZigBoi Music, has relied on the team at ZigBoi to ruffle his feathers a bit, change up his normal and make people take a second listen and look. “I released a reggae single- my first ever, recently. It’s called, “Once In A Lifetime,” and it’s on the Zig Boi produced, Royal Riddim with other Trinidad and Tobago vocalists like JahMel, Raskal, Makamillion and Kerry John. So far, it’s been getting a lot of love,” he said. Jesse is however looking at the bigger picture- the opportunity to expand his horizons of course, and become an even more versatile Caribbean musician. “The song’s been getting a lot of rotation at home and my team’s been making some strategic moves to make my presence felt in Jamaica, the US and the UK,” he said. Now, if you think he’s simply satisfied with this, think again. Jesse has been making inroads in the songwriting arena, having recently penned music for Barbados’ Alison Hinds, Biggie Irie and Trinidad and Tobago’s, Lyrikal, ahead of Barbados’ CropOver. He says he’s also working alongside other Caribbean carnival project organisers to deliver music for the upcoming Spice Mas in Grenada.
There’s a lot happening in the Caribbean- a lot for the world to see. College Boy Jesse seems set to infiltrate the scene and like many of you out there, we’re rooting for him all the way!
Now take a listen to the new single by College Boy Jesse.
Well known event promoter, Glenroy Watson, has passed away. He died of natural causes on April 1st, in Port -of- Spain, Trinidad.
Watson’s legacy in the event landscape in Trinidad and Tobago stands as one rooted in the philosophy of delivering value to patrons, something that was the benchmark of every ‘I Am Legend’ concert in T&T and certainly countless other events hosted across the region and internationally.
Hands on and meticulous in his approach, Watson prided himself as a no nonsense promoter.
Most recently, in the aftermath of Carnival 2026, he hosted the Majah Hype comedy show, ‘Majah Issues’, at the Southern Academy for the Performing Arts, in Trinidad and was preparing for a major concert event in Trinidad, at the time of his passing.
At this time, the bereaved extends gratitude to well- wishers and asks for privacy and understanding as preparations for Watson’s home-going ceremony get underway.
All further details will be relayed at a later time.
“If this sharing that I’m doing touches anyone, I’m truly grateful. None of us are perfect. Some days you’ll feel good, some days you won’t, but it’s all part of the journey. Sometimes what you’re looking for is right on the horizon, and the moment you give up, you miss it. If my testimony makes anyone feel something, then my work here is done.” – DESTRA GARCIA
Trinidad and Tobago received a musical showcase of spiritual awakening yet again this past Saturday, at Destra’s ‘Reflections: Sound. Spirit. Surrender.” The event took place at Queen’s Hall, St. Ann’s and proved to be a truly inspiring and uplifting musical experience.
From the onset, the show set a standard that fans of good music with powerful lyrics, would rave about for weeks. David Rudder – a cultural icon of Calypso music out of Trinidad and Tobago, welcomed the audience as he hit the stage first delivering the very fitting, ‘High Mas.’ It was a powerful blessing no doubt – something that would lead into a seamless spiritual production. He was subsequently joined on stage by Destra, something that created a full-circle moment that drew immediate emotion from the audience.
Destra with King David Michael Rudder.
Known for her unmistakeable vocal ability, Destra took her audience on a carefully curated musical journey, opening her set with Free Again before transitioning into slowed-down, soul-stirring renditions of some of her most beloved songs, including Love Somebody and Fly and with each performance, she revealed a different layer of her artistry, offering vulnerability, reflection, and strength.
One of the night’s most touching highlights came as Garcia shared the stage with her daughter, Xaiya, for a heartfelt duet of The Prayer. Beginning at the piano, Xaiya gently set the tone before joining her mother in song, creating an intimate moment that resonated deeply with the audience.
Destra’s daughter, Xaiya on the piano.
The production, which was creatively directed by Zara Bartels and Isoke Edwards, also showcased the incredible talent of father and son pan duo Martin and De’jean Cain as well as the Maria Regina Grade School and St. Joseph’s Convent Port- of- Spain choirs, whose vibrant and polished performances brought a refreshing, youthful energy to the stage. Gospel artiste, Nisa joined Garcia for a powerful duet of Bridge Over Troubled Water. She also performed her original composition Make Me Over, adding another layer of spiritual depth to the evening.
As the show built toward its finale, Garcia delivered a commanding rendition of Ella Andall’s Bring Down the Power, followed by classic hymns including A Little More Oil in My Lamp. This climactic segment was elevated by the presence of traditional belle dancers and African drummers, creating a rich, cultural fusion that brought the audience to its feet. Beyond the performances, the overall production, brought to life through Bridgette Wilson’s choreography and Atiba Borde’s costuming, stood out for its seamless execution, immersive ambience, and thoughtful storytelling, reinforcing Reflections as more than just a concert, but a transformative experience.
Reflections certainly delivered a powerful blend of music, filled with deep messages and meaning. In what is a very spiritual season, Destra, through the delivery of ‘Reflections,’ has carved out a space for inspiration and connection within Trinidad and Tobago’s cultural landscape – something that many would agree, is a necessity more than an option.
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