Highland “Dobby” Dobson, whose laid-back vocal style earned him hit songs in the pre-ska, rocksteady and reggae eras, died on July 21, 2020, at age 78 in Fort Lauderdale, Florida. Photo: Internet Source

His brother, Colin Morais, told the Jamaica Observer that Dobson succumbed to complications of COVID-19. He had suffered from dementia in recent years.

Born in Kingston, Dobson got involved in music while attending Kingston College in the late-1950s. He was a member of the school’s choir along with Norris Weir, who became famous as members of the group, The Jamaicans.

Though he had a minor hit song in the early 1960s with Cry A Little Cry, Dobson is best known for the 1967 hit song, I Am A Loving Pauper, a heartfelt ballad about an impoverished suitor determined to win his lady despite his lack of money.

Produced by Duke Reid, I Am A Loving Pauper has been successfully covered by Gregory Isaacs and Ruddy Thomas.

Dobson followed up with popular covers of Brook Benton’s Endlessly and That Wonderful Sound by Tom Jones. In 1968, he returned to Jamaican charts with Seems I’m Losing You, produced by Clement “Coxsone” Dodd.  Dobson was also a solid producer who directed roots-reggae group The Meditations on two albums.

In the 1990s he featured prominently in the rocksteady revival that took place in Jamaica, performing on shows like Heineken Startime. 

He was awarded the Order of Distinction in 2011 by the Jamaica Government for his contribution to the country’s music.

Dobson is survived by children, grandchildren, four brothers and three sisters.