Jesse Stewart known as “CollegeBoy” Jesse is a young, talented artiste and songwriter out of Cunupia, Trinidad who began performing at the very tender age of seven. His development began as a competitor in calypso and gospelypso competitions in the borough of Chaguanas.
In his junior years, he has always been a standout competitor and entertainer. Some of these events were theNational School’s Soca Monarch and Party Flava Talent Show where he was prized with the People’s Choice Award.
He was introduced to recording by Former Government Minister and Calypso icon, Winston Gypsy Peters who opened his home studio to provide musical development to the youth of the Chaguanas community and environs. Through this experience, his brother Shawn “Mr. Spine” Stewart who is now known to be a prevalentproducer/DJ/Promoter was inspired to establish their
very own recording studio ZigBoi Music, formerly known as Holy House Productions.
This studio provided the opportunity for Jesse to further his development as a songwriter, artiste and also background vocalist.
In 2007, Jesse’s musical journey took a slight detouras he earned an athletic football scholarship from theUniversity of Trinidad and Tobago’s Academy of Sport and Leisure. During this period, he was challenged with balancing his studies with sports while performing and releasing music with his team of music friends known as the Millionaire Family. Artistes on this team were the likes of Orlando Octave, Makamillion, Kerry John and Fadda Moses.
On his final year at UTT, he was selected for the “Soca
Warriors” team, which is the national football team of Trinidad and Tobago. This is whenthe “CollegeBoy” was born. He was given this nickname by the members on the footballteam as he was the only University/College student on the team at the time.