Sheldon Skeete first fell in love with Calypso music back in 1986 after watching David Rudder and Black Stalin battle for the Calypso Monarch title at the Demarche Gras in that year. At the age of 16 Sheldon performed his first Calypso at his Secondary, a song entitled “A Sister’s Plea” composed by his father, which gained second place despite being the lone Male competitor. In 2000, three years after migrating to England Sheldon discovered he had the gift to compose Calypsos. His first composition and recording “Woes of La Trinity” was he performed in 2001 in Trinidad’s Carnival and managed to qualify for every final. In 2002 he was second runner-up in the UK Calypso Monarch final with two selections. “Save Meh Kaiso” and “United We Stand”. Despite his demanding career in the Royal Airforce, he continues to write songs and returned to the Tent in 2010 with “Define Poverty”.
In 2011 Sheldon returned to Trinidad where he competed in Chaguanas finals. In August 2012, Sheldon clinched the UK Calypso Monarch title with a Song entitled “A Sightless Nation”. In 2013 Sheldon flew to Canada to perform at Toronto’s Carnival as part of his prize for winning the UK title. On his return to the UK, he successfully defended his UK Calypso Monarch title with his hit “Send Dem Afghanistan” and also captured the annual Calabash Award title as UK Calypsonian of the year.
The following year Sheldon attended Trinidad Carnival where he won Talparo’s Calypso Competition and was a regular performer at Cro Cro’s Icons Calypso Tent, receiving encores on a nightly basis. He was also invited to perform as a guest at the Klassic Russo Calypso Tent held at City Hall, Port of Spain. In 2014 Sheldon created history by becoming the youngest Calypsonian in the UK to win the Calypso Monarch three consecutive years with a song entitled “Voices”. This was followed in 2015 by winning the UK title four consecutive years with a song entitled “How to Capture the Monarchy”.