In May 1999, after touring in Brazil with other reggae singers, Brown started to show symptoms of illness. After returning to Kingston, Jamaica, on the evening of June 30, 1999, he was rushed to Kingston's University Hospital, suffering from cardiac arrest. Brown died the next day, and the official cause of his death was a collapsed lung.Brown's funeral was held on July 17, 1999 in Kingston. The service, which lasted for three hours, also featured live performances by Maxi Priest, Shaggy, and five of Brown's sons. Brown was then buried at Kingston's National Heroes Park.
Dennis Brown's first recording was "Lips of Wine" recorded for Derrick Harriott, but this was not released initially. He then recorded for Coxsone Dodd at Studio One, and Dodd released Brown's first single, "No Man is an Island". Brown recorded two albums for Dodd, No Man is an Island and If I Follow my Heart (the title track penned by Alton Ellis). During this time, Brown recorded material for Lloyd Daley ("Baby Don't Do It" and "Things in Life") and material for Derrick Hariott, which was eventually released as the Super Reggae and Soul Hits album. He also worked for Earl Hayles and the Charmaine label early in his career. "Money In My Pocket" was a UK Top 20 hit in 1979 (reaching #14 in the UK Singles Chart). This led to his contract with A&M Records, and to the formation of his own label, DEB records; which produced several of hits, including many by Junior Delgado.
His first commercially successful song internationally was "Money In My Pocket" on the Joe Gibbs label, and by the late 1970s, Brown had recorded and performed chart-toppers such as "Sitting & Watching", "Wolves and Leopards", "Here I Come" and "Revolution"; many featuring Sly and Robbie as the rhythm section. As the dancehall era of the 1980s arrived, Brown frequently recorded with King Jammy and Gussie Clarke. Trojan Records included Brown on their Jamaican Superstars compilation album (along with Gregory Isaacs, Delroy Wilson, Alton Ellis, John Holt and Pat Kelly), calling him the "perfect superstar". The compilation was released in 1998, the year before his death.