Jai's 1988 debut single "Sumintra" told the tale of an Indo-Trinidadian woman from Debe who informed her boyfriend of her preference for soca over the music of Indian artist Lata Mangeshkar. Jai returned the following year with "Pumping", then "Bolo" and "Show Me Yuh Motion". His 1993 song "Wine on a Bumsee" signalled Jai's exit from the soca world, opting for the "chutney soca" arena, in which he continues to perform. Jai released Chutney Vibrations, a compilation with soca chutney rhythms and his re-reading of the Juma[disambiguation needed]. His most commercially successful release is "Mor Tor" featuring fellow Trini soca star Machel Montano. In 2007 he released songs such as "Aj Bhi Jeen" and "Bodekidal", followed by "Barman". Jai has won Chutney Soca Monarch a record-breaking six times. In 2011, he won his 6th title with the song "White Oak and Water".
In 2001 he tied for first place (with Bunji Garlin) for the "Young King" title and placed second in 2010's "Chutney Soca Monarch".
He was crowned champion at the 2011 Chutney Soca Monarch, and walked away with $2 million in prize money.