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The Jiving Juniors were formed in 1958 by students at Excelsior and Kingston Colleges. The members included Eugene Dwyer, Herman Sang, Maurice Winter, Derrick Harriott (born 1942). In the late '50s, the group recorded for many in that period's major producers, including Edward Seaga, Blue Beat, Duke Reid, and Clement "Coxsone" Dodd. In 1960, Reid released "Lollipop Girl" and the quartet rocketed to the top of the newly established Jamaican pop charts. The R&B ballad characterizes the romantic tone of many of their tunes and that same year, "My Heart's Desire" also hit big.

The spiritual doo wop "Over the River" was their next major success. An important route marker on the road of Jamaican music, the song is a laid-back boogie with a guitar offbeat so heavily accented it sounds nearly indistinguishable from ska. Although Dodd didn't release the record until 1961, it was possibly recorded much earlier – perhaps as early as 1959 – and features trombonist Rico Rodriguez's first solo. Their last major hit came with the 1962 release "Sugar Dandy." While hugely popular, the track proved the swan song for the group's doo wop style, saccharine lyrics, and Harriott's sometimes shrill falsetto.

Later that year, as Jamaica won its independence and ska began to dominate the music scene, the Jiving Juniors split up without scoring a major hit in the new genre. Harriott departed to form his Crystal label and the rest of the group left Jamaica a few years later for destinations north. While still in Jamaica, Eugene Dwyer tried to start two groups, one called Zodiac and another called the Pacesetters, but neither had much success and he, too, left Jamaica in 1980. Harriott was the most successful talent to emerge from the group, both as a solo singer on "Solomon" and "Loser" and as a producer, recording dozens of artists up through the 1990s.

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