Highland "Dobby" Dobson (b. 1942, Kingston, Jamaica) is a reggae singer and producer, nicknamed 'The Loving Pauper' after one of his best known songs.

Dobson began singing at school, and successfully took part in Vere Johns Opportunity Hour talent contest as a member of The Twilights. He began recording in the ska and rocksteady eras as a member of Chuck and Dobby, and The Deltas, the latter along with Howard Barrett (who later formed The Paragons). The group recorded a few tracks for Lindon and Sonia Pottinger, with "Cry a Little Cry" topping the RJR chart, but soon split up, with Dobson continuing to record for Pottinger. He later moved on to work with both Coxsone Dodd and Duke Reid, recording as a member of both The Virtues and The Sheiks, and recorded "Loving Pauper" with Reid, which became his signature tune. Despite his musical success, Dobson kept his job as a salesman and proof-reader for The Jamaican Gleaner. In 1971, he recorded "That Wonderful Sound" for Rupie Edwards, which sold over 40,000 copies in the Caribbean, and was followed up by the equally successful "Endlessly", which was also a minor hit on the UK Singles Chart.

Disappointing album sales led Dobson to move into production, including The Meditations' late 1970s albums Message From The Meditations and Wake Up, as well as early work by Barrington Levy. In 1979, Dobson emigrated to New York, where he worked in real estate, although he would still occasionally visit the recording studio, and performed at both the Reggae Sunsplash and the Reggae Sumfest festivals. He continues to be very popular with international fans, and is still regularly releasing albums.