Holt was born in Kingston in 1947. By the age of 12, he was a regular entrant in talent contests run at Jamaican theatres by Vere Johns. He recorded his first single in 1963 with \"I Cried a Tear\" for record producer Leslie Kong, and also recorded duets with Alton Ellis. He achieved prominence in his home country as lead singer of The Paragons, with whom he enjoyed a string of hits, including \"Ali Baba\", \"Tonight\", \"I See Your Face\", and the Holt penned \"The Tide Is High\" (later made famous by Blondie and also covered by Atomic Kitten). \"Wear You To The Ball\" was another of his hits with The Paragons, later covered by U-Roy. During his time with the Paragons, he also recorded solo material for Studio One (including \"Fancy Make-up\", \"A Love I Can Feel\", \"Let's Build Our Dreams\", and \"OK Fred\") and Prince Buster (\"Oh Girl\", and \"My Heart Is Gone\").
Holt's style, notably slower and more romantic than most of his contemporaries, is a recognisable forerunner of the lovers rock style which developed in the UK during the 1970s. \"Don't Want To See You Cry\" was one of Holt's many Jamaican hits. The lyrics about \"moving to a far away land\" and leaving loved ones behind must have rung true for many Jamaicans in the 1960s.
While Holt became well-known internationally for these lushly produced ballads, in Jamaica he also recorded more roots-oriented material such as \"Up Park Camp\", as well as a short-lived attempt at crossing over into disco. Holt further explored his more rootsy side on the album Police In Helicopter from 1983, the title song from which became a hit.