2023 Calypso Monarch iWeb posing with Trophy (Photo credit: Kemar Holder)

“The brain is the centre of wisdom – cerebral cortex and the cerebellum. If you dare to delve a little deeper, check the medulla oblongata. Yes, in the field of neurology, we must understand how exactly the human brain does be functioning, with the decisions I see people making…

– Brain, written by The Water Street Boys

   As the charming Ian “iWeb” Webster settled into our interview, his determined voice alluded to his extraordinary fate. His pronounced passion for calypso music and unyielding commitment to his craft was expressed with fervour — the same fiery intensity the Pic-O-De-Crop audience witnessed on Friday August 4th, when he was named the 2023 Calypso Monarch for his unparalleled, theatrical performance of “Brain”, making him a four-time competition winner. And yet, even on his ever-expanding path of greatness, his humility and openness permeated our conversation, revealing the unexpected twists and turns that have shaped his musical odyssey. 

Calypso’s Theatrical Maestro

   In 2001, iWeb embarked on his musical journey intending to secure a spot in the Junior Monarch Finals. Though the attempt was unavailing, he remained undaunted and adamantly pursued his dreams. At the inception of his career, he performed with the Synergy band and soon after, joined the Lion’s Den Calypso tent. This valuable experience allowed him to explore the enticing realm of social commentary, not only as a performer but also as a backup singer. 

   It was in 2002 that iWeb’s artistic brilliance began to emerge. At this time, he worked under the guidance of his then manager Shawn Clarke. That year, the public bore witness to his theatrical prowess as he fearlessly commented on the first illegal same-sex union in Barbados with the song “The Wedding Reply”. 

   Although “The Wedding Reply” did not make it to the Pic-O-De-Crop semi-finals, it marked a seismic shift in iWeb’s career, propelling him into the spotlight and cementing him in the hearts of Barbadians. The song’s powerful lyrics, coupled with iWeb’s mesmerising stage presence as he portrayed a character, deeply moved audiences, leaving an impact that still lingers. 

   The following year, iWeb’s undeniable talent earned him a remarkable third place in the finals, where he performed “I Know Dat” and “Nation of Shows”. Despite this taste of success, and bold decision to leave Synergy band and join Double Explosion, iWeb stepped away from the stage. A search for a deeper understanding of himself led to a quest for spiritual growth. Leaving competitions and prospective crowns behind, he ventured into the formal study of music and theology in Trinidad, and the insights he gained during this period are now evident in his songwriting.

   The song “Brain” has attracted praise in all its monumental glory, and is also a testament of iWeb’s wisdom and refined eloquence. It addressed real-world problems and highlighted instances of defective reasoning. Issues such as crime, IMF debt, and increasing taxes were skillfully described as being analogous to poor brain function. An excerpt of the lyrics state:

“The brain is the centre of wisdom – cerebral cortex and the cerebellum. If you dare to delve a little deeper, check the medulla oblongata. Yes, in the field of neurology, we must understand how exactly the human brain does be functioning, with the decisions I see people making…

Tell me are the neurons inactive? Is there an issue with the synapses or is the country just going insane? Man, it’s like we don’t use we brain.”

   “Brain” scored 128 points in the Pic-O-De-Crop competition, surpassing AC with “Anansi and the Big Bad Ram” in second place, and Quon with “Sing Quon Sing” in third. For iWeb, though, this career is not about achieving fame; rather, it is about creating music that touches souls, challenges beliefs, and inspires positive change. 

To read the full story, click here.

iWeb performing Brain at Golden Square Freedom Park, Barbados

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