Healthy Body, Bum Flick, and All Fruits Ripe were some of his popular songs.
Little Lenny
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But his biggest hit was Gun Inna Baggy, a suggestive song that got him expelled from Kingston College at age 17.
In his heyday, Little Lenny recorded four albums, three for Shocking Vibes and the other for Washington DC's RAS Records.
Now 41, the father of seven children operates a publishing business in Kingston. In addition to producing business cards and billboards, his company rents vehicles for funeral.
Although not as involved in the music business, Little Lenny (real name Nigel Grandison) says he still records.
Early this year, he released a four-track EP titled Little Lenny Reminiscing.
It was produced by Sylvester Gordon and includes covers of The Paragons' On The Beach (with U Roy) and Alton Ellis' Live and Learn.
"It is more of a hobby for me as I am more focused on the day-to-day running of my business," Little Lenny told the Sunday Observer.
Things were not so bright for him in the mid-1990s. His once promising career nose-dived and according to the deejay, so did his personal life.
"I was one of the fallen entertainers. My songs were chart-toppers but I made nothing from music as I was robbed by producers," he said. "I was a fool to what I didn't know. I lost my home and family because I couldn't afford to take care of them...I was on my face but I tried my best not to show it."
Little Lenny remembers things getting so bad for him that at one stage, he began stealing electricity and water.
"There were times that I just sat at home and cried. Whoever said that poverty isn't a crime was lying because poverty leads you to think all type of things... some of them negative," he said.
Little Lenny says he was motivated to start his own business after hearing a moving sermon by a pastor. He launched it in the late 1990s and has been back on his feet since.
"I am not rich but I am living way better than when I had a career in music," he stated