World of Jamaican Music

Discover artists and hear songs from everyone on the site! Log in to Spotify in this browser to hear full songs. SourcesYour Voice

An illustrated map of the creators of Jamaican music and how they are connected.

Remembering Derrick Harriott (1939-2026), rocksteady singer and producer. Read his story →

Josey Wales

Artist. Reggae, dancehall

Active
1977-present
Sunrise
October 9, 1958, West Kingston, Jamaica
Also known as
The Outlaw, The Colonel, Colonel Josey Wales

Josey Wales (born Joseph Winston Sterling) took his name from the 1976 Clint Eastwood film and is known as the Outlaw and as the Colonel. He was among the leading deejays of the early 1980s, alongside Brigadier Jerry, Yellowman, and his sound system partner Charlie Chaplin.

He was born in St. Mary and began in 1977 on the Roots Unlimited sound system, where he often sparred with Burro Banton. He moved to King Sturgav Hi-Fi, owned by U-Roy, and it was there that he teamed with Charlie Chaplin. Wales, Chaplin, and Brigadier Jerry performed together as Three the Hard Way.

His voice is gruff and his delivery half spoken and half sung. What separated him from Yellowman was the content. He has said his early sound system lyrics were both sexual and violent and that he changed them out of respect for U-Roy; from that point his material stayed conscious and Rastafarian, at a time when slackness was taking over the dancehalls.

He became widely popular in the early 1980s performing on Henry "Junjo" Lawes's Volcano sound system and recording for Lawes's label of the same name, including "Bobo Dread" and "Leggo Mi Hand," which reached number four in Jamaica. The Outlaw Josey Wales (1983) was his first album. He moved to King Jammy's in 1985 and recorded "Na Lef Jamaica" and "Water Come a Mi Eye." In the late 1980s and early 1990s he was among the veterans who found success on Philip "Fatis" Burrell's Exterminator label. He was made an Officer of the Order of Distinction on Heroes' Day, October 16, 2017.

Last updated October 21, 2026

Connections

Notes

  1. He took the name from the 1976 film The Outlaw Josey Wales. Simone Morgan-Lindo, "Josey Wales Rides to King's House," Jamaica Observer, August 15, 2017, https://www.jamaicaobserver.com/2017/08/15/josey-wales-rides-to-kings-house/. The Rough Guide places him in a line of deejays who named themselves after screen characters, and adds that "the Colonel, as he was called, was always more than just a gruff voice." Steve Barrow and Peter Dalton, The Rough Guide to Reggae, 3rd ed. (London: Rough Guides, 2004), 57, 258. Wales dated the nickname to his arrival on Stur-Gav: "It was a street thing." "Josey Wales: Reggae Geel 08/2008," Rebelbase, August 1, 2008, https://rebelbase.be/interviews/detail/josey-wales---reggae-geel-082008.
  2. The Rough Guide calls Wales and Chaplin "the two deejays most seriously to rival Yellowman" and says Wales was Yellowman's "most serious rival" in 1984. Barrow and Dalton, Rough Guide to Reggae, 258, 260. Bradley names Chaplin, Brigadier Jerry, and "mostly, Josey Wales" as the deejays who kept the music cultural. Lloyd Bradley, This Is Reggae Music: The Story of Jamaica's Music (New York: Grove Press, 2001), 506.
  3. The Observer calls him "St Mary-born." Morgan-Lindo, "Josey Wales Rides to King's House." Wikipedia, citing Colin Larkin's Guinness Who's Who of Reggae, gives 1977 and the rivalry with Burro Banton, and notes that some sources give his birthday as June 24 rather than October 9. "Josey Wales (singer)," Wikipedia, accessed October 2, 2026, https://en.wikipedia.org/wiki/Josey_Wales_(singer). Wales recalled Roots Unlimited, "at Waltham Park Road," as "small-time stuff really." "Josey Wales: Reggae Geel."
  4. Wales said he "ended up with King Sturgav around '78 or '79." "Josey Wales: Reggae Geel." The Rough Guide says Ranking Joe "was followed on Stur-Gav by Charlie Chaplin, Josey Wales and Brigadier Jerry," and that the sound, out of action for a year after the 1980 election, was relaunched with Wales and Chaplin as its stars. Barrow and Dalton, Rough Guide to Reggae, 189, 258.
  5. Morgan-Lindo, "Josey Wales Rides to King's House."
  6. The Rough Guide places him in "the rockstone-voiced deejay tradition that stretches back to Prince Jazzbo." Barrow and Dalton, Rough Guide to Reggae, 258.
  7. Wales told the Observer: "My songs were a bit too sexy while the gun tunes were graphic, but I then decide to change up my music because I had a lot of respect for Daddy U-Roy." Morgan-Lindo, "Josey Wales Rides to King's House." Bradley says Yellowman's clash album with Chaplin, Slackness vs Pure Culture, "pointed the way forward." Bradley, This Is Reggae Music, 508.
  8. The Observer says his popularity grew on Volcano in the early 1980s. Morgan-Lindo, "Josey Wales Rides to King's House." The Rough Guide calls "Let Go Mi Hand" his "first Jamaican hit" and places him in the first rank of Volcano's deejays. Barrow and Dalton, Rough Guide to Reggae, 258, 269. The chart position is from Wikipedia, citing an NME Jamaica chart of September 10, 1983. "Josey Wales (singer)."
  9. The Rough Guide treats The Outlaw Josey Wales and No Way Better Than Yard as "his first two albums." Barrow and Dalton, Rough Guide to Reggae, 259. Wikipedia dates the first to 1983 and lists Josie Wales Meets Early-B in the same year. "Josey Wales (singer)."
  10. The Rough Guide says he recorded for King Jammy "as the music reinvented itself yet again in the decade's second half" and sounded "particularly at home on Jammy's rhythms." Barrow and Dalton, Rough Guide to Reggae, 258, 301. Discogs lists both singles as 1987 Jammy's releases. "Josey Wales, Water Come A Mi Eye," Discogs, accessed October 2, 2026, https://www.discogs.com/release/2836800-Josey-Wales-Water-Come-A-Mi-Eye; "Jose Wales, Nah Lef Ya," Discogs, accessed October 2, 2026, https://www.discogs.com/release/5837730-Jose-Wales-Nah-Lef-Ya.
  11. Katz names him first among the "veteran artists" with whom Exterminator "found success" in this period, after 1987 and before 1993, when Burrell was recording mostly at Gussie Clarke's Music Works. David Katz, "Philip 'Fatis' Burrell Obituary," Guardian, December 6, 2011, https://www.theguardian.com/music/2011/dec/06/philip-fatis-burrell.
  12. Morgan-Lindo, "Josey Wales Rides to King's House."

World of Jamaican Music: the whole map