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The achievements of Delroy Wilson as a budding teenage sensation of the 1960s ska era is well documented in Jamaica’s music history, and was showcased in the last Music Diaries.

He had, by 1966, when ska was going through a transition, stamped his class as a rarity, the wonder boy of Jamaican music. But Wilson’s achievements go way beyond the boundaries of ska, taking us into the realms of what was to become known as rocksteady.

By the time this period dawned in late 1966, Wilson had just turned 18, and his voice broke just in time to fit into the slower, more elegant and rhythmic rocksteady beat.

His version of the Tams’ Dancing Mood, not only heralded a shift in the beat of Jamaican popular music, but signalled a real turning point in his career, from ‘Little Delroy’, as he used to be called, to a more mature-sounding singer.

Enshrined as an ‘oldie but goodie’ and a No.1 hit in Jamaica in 1966, Dancing Mood was also Wilson’s biggest hit up to that point.

This wind of change, which many musicologists termed ‘transition ska’, saw Wilson recording several other songs at Studio One with that tempo, the most popular ones being Riding For A Fall (another Tams original),It’s Impossible (written by Bob Andy), Get Ready (a Temptations classic of 1966), and his self-penned Ungrateful Baby. Wilson told me Ungrateful Baby was his favourite composition, and perhaps for good reason.

Delroy Wilson


Ungrateful Baby speaks about a man who fate has dealt many blows (incidentally, he lost an eye while parting a fight at school), and who has had many travails of the heart with women.

The recording gave full expression to Wilson’s emotions in one of music’s most heartbreaking laments.

I saw you pack your things and say you’re gonna leave me, I don’t know the reason why,

just because you found somebody new, you wanna leave me to cry.

Although I broke your heart and tore it all apart, but please don’t treat me this way

Remember what you say, you’ll never be this way,

and still you broke your promise to me.


By the time the rocksteady beat got into full swing in 1967, Wilson was a star. The new beat brought his now-mature voice into full focus and generated an almost unending flow of hits, which rode high on the charts for weeks during mid 1967. The Adam Wade classic, Rain From The Skies, was one such recording. Once Upon A TimeI’m Not A King and Feel Good All Over, the title track from one of the biggest-selling albums from Studio One, were others.

On the ‘gayfeet’ record label, controlled by Sonia Pottinger, Wilson had the commendable releases I’m The One Who Loves You, and Put Yourself In My Place, a couple years later. Have Some Mercy, ostensibly a love song, saw Wilson again pleading with fate for help with another relationship. It was another big hit for him.


A few years earlier, 1971 to be exact, Wilson consoled himself with the recording, Better Must Come, which expressed his despair at his slow personal advancement, compared to others who have contributed less to the development of music.

“I wrote that song when things were going on that were a little hard for me. I get the idea, and I kept humming the tune to keep me from going crazy. So I wrote the song. I ran into producer Bunny Lee and the song sky rocketed into the Jamaican charts,” said Wilson.

In the run-up to the 1972 general elections, Better Must Come became enormous popularity when it was used as the campaign song for the People’s National Party.

The recording also holds pride of place, as being an inspiration to many of the downtrodden. The song also helped in no small way to boost Bunny Lee’s status as a record producer.

Wilson recorded several other successful sides for Lee, including Stick By Me, a Shep and the Limelites original, which was later reworked by John Holt, This Old Heart Of MineWon’t You Come Home Girl, and I Can’t Explain.

Wilson was one of the many great musicians born in that Mecca of music known as Trench Town. He was born there on October 5, 1948 and attended the Boys’ Town Primary School in the community, where he got his first exposure to performance at school concerts. Wilson is quoted as saying “My recordings I started when I was about 12, but I was little, so they put me on a Red Stripe box, and I sing my first song”. That was at Federal Records in 1962.


The entrepreneurial side of his character Wilson revealed, when he formed his own record label (W&C), towards the late 1960s in association with another early musical stalwart, Stranger Cole.

The label produced two distinguished recordings in Once Upon A Time and I Want To Love You.

He then joined with Ken Boothe, The Gaylads and The Melodians to form Links Recording Company which had an ephemeral life span.

By the time Wilson fully entered the reggae era of the 1970s, he had taken the rocksteady and reggae genres to new levels and proved beyond a doubt why he was dubbed ‘The Dean of Reggae’.

He continued to record for several labels during the 1970s and 1980, with perhaps the most memorable recordings Channel One’s It’s A Shame and Call On Me; Jackpot’s Cool Operator; Beverley’s Gave You My Love and Show Me The Way; Gussie Clarke’s You’re Worth Your Weight In Gold; Harry J’s Last Thing On My Mind, and Jo Gibbs, Pretty Girl, in addition to an album, consisting mainly of Studio One remakes for Bunny Lee.

Wilson’s career, however, began to flounder in the mid-1980s and his hits declined. Apart from a partial revival in the musical digital age, things really took a downturn for him at the end of the 1980s. Strong drink exacerbated his other misfortunes and, after a short illness, he succumbed on March 6, 1995.


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