During his prolific career, which began in the late 1960s when he was aged eleven, he recorded more than 75 albums and was one of the major stars of lovers rock, a subgenre of reggae.

[4] He regularly hung around JJ's record store on Orange Street in the rocksteady era and his relatives and neighbours would often throw Brown pennies to hear him sing in their yard.

[4] Brown's first professional appearance came at the age of eleven, when he visited "Tit for Tat" a local West Kingston Nightclub where his brother Basil was performing a comedy routine, and where he made a guest appearance with the club's resident group, the Fabulous Falcons (a group that included Cynthia Richards, David "Scotty" Scott, and Noel Brown).

[4] When the group performed at a JLP conference at the National Arena, Brown sang two songs – Desmond Dekker's "Unity" and Johnnie Taylor's "Ain't That Loving You" – and after the audience showered the stage with money, he was able to buy his first suit with the proceeds.

[9] He went on to record for several producers including Lloyd Daley ("Baby Don't Do It" and "Things in Life"), Prince Buster ("One Day Soon" and "If I Had the World"), and Phil Pratt ("Black Magic Woman", "Let Love In", and "What About the Half"), before returning to work with Derrick Harriott, recording a string of popular singles including "Silhouettes", "Concentration", "He Can't Spell", and "Musical Heatwave", with the pick of these tracks collected on the Super Reggae and Soul Hits album in 1973.

This original version of "Money in my Pocket" was in fact produced by Winston "Niney" Holness on behalf of Gibbs, with musical backing from the Soul Syndicate.

[12] In the same year, Brown performed as part of a Christmas morning showcase in Toronto, along with Delroy Wilson, Scotty, Errol Dunkley, and the Fabulous Flames, where he was billed as the "Boy Wonder of Jamaica" and was considered the star of the show in a local newspaper review.

[13] In 1973, Brown was hospitalized, due to fatigue caused by overwork; at the time, rumours spread that he only had one lung and had only a week to live, or had contracted tuberculosis.

[16] On their return to Jamaica, Brown and Holness resumed recording in earnest with tracks for a new album, including "So Long Rastafari", "Boasting", and "Open the Gate".

[25] The biblical-themed sleeve and portrait of Haile Selassie on the jacket back complemented the roots reggae tracks on the album, including "Repatriation", "Jah Can Do it", and cover versions of Earl 16's "Malcolm X" and Clive Hunt's "Milk and Honey".

[29] Brown had further success himself with a discomix of "How Could I Leave You", a version of The Sharks' rocksteady standard "How Could I Live" with accompanying toast by Prince Mohamed.

In March 1978, Brown flew to Jamaica, where he was booked at the last minute to perform at the One Love Peace Concert at the National Arena, backed by Lloyd Parks' We The People Band.

Initially released as a discomix featuring a new version of "Money in my Pocket" and the deejay version "Cool Runnings" by Price Mohamed, which became unavailable for a time after quickly selling out its first pressing, this single gave Brown his first UK Top 40 hit, reaching number 14 the following year and becoming one of the biggest international hits in Jamaica's history,[32][33] after crossing over first into soul clubs and then rock clubs.

[36] While his association with A&M had taken him in a more commercial pop direction, Kingston's music scene had shifted towards the new dancehall era, and Brown enthusiastically adapted to the new sound, recording for some of the genre's major producers including Prince Jammy and Gussie Clarke.

He had developed respiratory issues, probably exacerbated by longstanding problems with drug addiction, mainly cocaine, leading to him being taken ill in May 1999 after touring in Brazil with other reggae singers, where he was diagnosed with pneumonia.

"[48] Dennis Brown was an inspiration and influence for many reggae singers from the late 1970s through to the 2000s, including Barrington Levy, Junior Reid, Frankie Paul, Luciano, Bushman, and Richie Stephens.

[39] In July 1999, a group of UK-based musicians and more than fifty vocalists working under the collective name The British Reggae All Stars (including Mafia & Fluxy, Carlton "Bubblers" Ogilvie, Peter Hunnigale, Louisa Mark, Nerious Joseph, and Sylvia Tella) recorded "Tribute Song", a medley of six of Brown's best-known songs, in memory of Brown.

He was honoured on the first anniversary of his death by a memorial concert in Brooklyn, which featured performances from Johnny Osbourne, Micky Jarrett, Delano Tucker, and Half Pint.

[51] In 2008, the Dennis Brown Trust announced a new internet radio station, dedicated solely to the music of Dennis Brown, and in the same month a tribute concert was staged by the Jamaican Association of Vintage Artistes and Affiliates (JAVAA) featuring Dwight Pinkney, Derrick Harriott, Sugar Minott, George Nooks, and John Holt.

The NPR "50 Great Voices" list includes Nat King Cole, Ella Fitzgerald, Mahalia Jackson and Jackie Wilson among others.

[54] On 6 August 2011, being the 49th anniversary of the country's independence, the Governor-General of Jamaica posthumously conferred the Order of Distinction in the rank of Commander (CD) upon Brown, for his contribution to the Jamaican music industry.