0
Charlie Chaplin
Charlie Chaplin
Jamaican dancehall and ragga deejay and singer
1
Yellowman
Yellowman
Jamaican reggae singer
2
Johnny Ringo
Johnny Ringo
Jamaican musician
3
Burro Banton
Burro Banton
Jamaican reggae musician
4
Admiral Bailey
Admiral Bailey
Jamaican musician
5
Beenie Man
Beenie Man
Jamaican reggae and dancehall singer
6
Professor Nuts
Professor Nuts
Jamaican musician
7
Peter Metro
Peter Metro
Jamaican DJ
8
Lieutenant Stitchie
Lieutenant Stitchie
Jamaican musician
9
Massive Dread
Massive Dread
Reggae musician
10
Fathead
Fathead
musician
11
Tiger
Tiger
Jamaican dancehall musician
12
Dillinger
Dillinger
Jamaican musician
13
U-Roy
U-Roy
Jamaican musician
14
Sister Nancy
Sister Nancy
Jamaican musician
15
Super Cat
Super Cat
Jamaican deejay
16
Red Dragon
Red Dragon
singer
17
Henry "Junjo" Lawes
Henry "Junjo" Lawes
Jamaican record producer
18
Johnny Osbourne
Johnny Osbourne
Jamaican musician
19
Bounty Killer
Bounty Killer
Jamaican reggae and dancehall deejay
20
Captain Sinbad
Captain Sinbad
Jamaican musician
21
King Stitt
King Stitt
Jamaican reggae musician
22
Triston Palmer
Triston Palmer
Jamaican musician
23
Trinity
Trinity
Jamaican reggae artist
24
Mega Banton
Mega Banton
Jamaican reggae musician
25
General Trees
General Trees
Reggae musicians
26
Prince Jazzbo
Prince Jazzbo
Jamaican reggae deejay
27
Jah Lloyd
Jah Lloyd
Jamaican singer, deejay and producer
28
Sugar Minott
Sugar Minott
Jamaican musician
29
Prince Buster
Prince Buster
Jamaican singer-songwriter and producer
30
Chaka Demus
Chaka Demus
Jamaican musician
31
Tinga Stewart
Tinga Stewart
Jamaican singer
32
Papa San
Papa San
Jamaican singer
33
Bunny Lee
Bunny Lee
Jamaican record producer
34
David Jahson
David Jahson
Jamaican musician
35
The Morwells
The Morwells
36
Toyan
Toyan
Jamaican musician
37
Popcaan
Popcaan
Jamaican Dancehall artiste
38
Daddy Screw
Daddy Screw
Jamaican DJ
39
Nicodemus
Nicodemus
Jamaican musician
40
Barrington Levy
Barrington Levy
reggae and dancehall artist from Jamaica
41
Ini Kamoze
Ini Kamoze
Musical artist
42
Dennis Brown
Dennis Brown
Jamaican reggae singer
43
Shinehead
Shinehead
Jamaican singer
44
Errol Dunkley
Errol Dunkley
Jamaican musician
45
Robert Ffrench
Robert Ffrench
Jamaican musician
46
Buju Banton
Buju Banton
Jamaican musician
47
Lone Ranger
Lone Ranger
Reggae musician
48
Perfect
Perfect
reggae singer
49
U Brown
U Brown
Jamaican musician
50
Little John
Little John
Reggae
51
Nitty Gritty
Nitty Gritty
Jamaican musician
52
Ranking Joe
Ranking Joe
Reggae musician
53
Big Youth
Big Youth
Jamaican deejay
54
Cornell Campbell
Cornell Campbell
Jamaican musician
55
Leroy Smart
Leroy Smart
Jamaican musician
56
Spragga Benz
Spragga Benz
Jamaican musician
57
Jah Thomas
Jah Thomas
Jamaican musician
58
Eek-A-Mouse
Eek-A-Mouse
Jamaican reggae musician
59
Gregory Isaacs
Gregory Isaacs
Jamaican singer
60
Anthony Johnson
Anthony Johnson
Jamaican singer
61
Shabba Ranks
Shabba Ranks
Jamaican dancehall musician
62
Big Joe
Big Joe
Jamaican musician
63
Keith Hudson
Keith Hudson
Jamaican musician
64
Gussie Clarke
Gussie Clarke
Jamaican record producer
65
Mad Cobra
Mad Cobra
Jamaican musician
66
Sanchez
Sanchez
Jamaican reggae singer
67
Alton Ellis
Alton Ellis
Jamaican musician
68
Cocoa Tea
Cocoa Tea
Jamaican musician
69
Kiprich
Kiprich
Jamaican musician
70
Half Pint
Half Pint
Jamaican dancehall, ragga, and reggae singer
Intro
Jamaican singer
Genres

Josey Wales OD (born Joseph Winston Sterling, June 24 1956 in St. Mary, Jamaica) is an influential Jamaican dancehall deejay. He was considered, along with Brigadier Jerry, Yellowman and sound system partner Charlie Chaplin, one of the best deejays of the 1980s. Wales is named after the 1976 Western movie character from The Outlaw Josey Wales, played by Clint Eastwood, and subsequently nicknamed "The Outlaw".

His career began in the late 1970s, first starting as a deejay on the Roots Unlimited sound-system where he often sparred with Burro Banton, and later performing over U-Roy-owned King Sturgav sound system. He gained even more popularity in the early 1980s performing over Henry "Junjo" Lawes's Volcano sound system, and recording singles such as "Bobo Dread" and "Leggo Mi Hand" for Lawes' label of the same name, as well as later hits for George Phang's Power House label, most noticeably "Undercover Lover".

He was shot and robbed in a Kingston bar in 1997, an incident that he dealt with in the country and western hit "Bushwacked". He survived the robbery, and after his discharge from a hospital, he went to the United States and bought an ambulance to donate for the Kingston General Hospital.

He appeared in Shaggy's "Bad Man Don't Cry" video, and by 2014 had begun recording new material.

In October 2017, he was awarded the Order of Distinction by the Jamaican government.
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