c.1955, Clarendon, Jamaica, West Indies. McGregor entered the Jamaican music business at the precocious age of seven, singing backing vocals with ska duo the Clarendonians at Coxsone Dodds Studio One. He stayed with Dodd throughout the rest of the decade and into the early 70s, acting as a session drummer and backing singer as well as cutting sides such as Why Did You Do It, and Do Good (c.1965) with Clarendonian Ernest Fitzroy Wilson as Freddie And Fitzy, versions of Johnny Aces Pledging My Love and Junior Byles Beat Down Babylon (c.1972), and his own compositions, Go Away Pretty Woman, What Difference Does It Make and Why Is Tomorrow Like Today. In 1975, after adopting the Rastafarian faith through the Twelve Tribes organization, he recorded two of his finest singles, I Man A Rasta and Rastaman Camp, both heavyweight slices of roots Rasta reggae. In the early 70s he worked stage shows as lead singer with the Generation Gap and Soul Syndicate bands and maintained strong links with both sets of musicians throughout his career. The late 70s saw his star rise with excellent singles such as Jogging for Tuff Gong, the herbsman anthem Natural Collie, based around the melody and arrangement of Norman Collins soul opus, You Are My Starship, and Mark Of The Beast, Leave Yah, and a cover version of George Bensons Love Ballad, all for Earl Chinna Smith. Winston Niney Holness produced his debut set, Mr McGregor, and there were further recordings for Studio One including Homeward Bound, Come Now Sister, Africa Here I Come, and the classic Bobby Babylon. In 1979, McGregor was also involved in the production of Judy Mowatts excellent Black Woman.
McGregors reputation as one of the most vocally gifted singers in reggae, able to turn his hand to lovers or roots material with equal potency, had been increasing steadily when he recorded Big Ship for Linval Thompson. Released in the UK on Greensleeves Records, the album was a great success. He followed this up with Love At First Sight (1982) for Joe Gibbs. Coxsone capitalized on McGregors popularity, which by that time was rivalling that of Dennis Brown and Gregory Isaacs, with the same years I Am Ready, which, like its predecessor, was comprised mainly of singles and previously unreleased tracks from the singers sojourn at Studio One in the early 70s. In 1984, McGregor inaugurated his own Big Ship label with Across The Border, and secured a licensing agreement with RAS Records in the USA for the release of Come On Over. In 1985, he recorded the duet Raggamuffin with Dennis Brown for Gussie Clarke, and the dancehall hit Dont Hurt My Feelings for George Phangs Powerhouse label. Throughout the 80s, McGregor enjoyed a position as one of reggaes most popular performers, touring the world with the Studio One Band, and enjoying a huge hit in Colombia with a version of the Sandpipers Guantanamera, sung in Spanish, for RAS.
McGregor signed a recording contact with Polydor Records which resulted in the UK chart-nudging Push Come To Shove (1987) and That Girl, finally achieving a UK hit with a cover version of Main Ingredients Just Dont Wanna Be Lonely, which reached number 9 in August 1987. Now established as a senior reggae statesman, McGregor completed a pair of albums, Sings Jamaican Classics and Jamaican Classic Volume 2, on which he offered his interpretations of reggae standards such as Little Roys Prophecy and Derrick Harriotts The Loser, retitled The Winner. McGregor again narrowly missed the UK charts with his interpretation of Justin Hinds And The Dominoes Carry Go Bring Come (1993), but has since had huge success in the reggae charts with his production of Lucianos Shake It Up Tonight, sung over the rhythm used for his own Seek And You Will Find, which also provided the vehicle for Big Youths excellent Jah Judgement. Already a veteran in the business McGregors future as a reggae superstar looks assured.
Source: The Encyclopedia of Popular Music by Colin Larkin. Licensed from Muze.