Born in Newham, London, Charles started his career at Clapton F.C.,[1] but first came into notability at Nottingham Forest, when he became a regular alongside Roy Keane, making his debut on 7 November 1987.
[7] On 29 July 1993, he made a £750,000 move to Derby County, appearing 76 times for them during a two-year spell, which included honours for PFA Team of the Year in 1993–94.
On 6 January 1995, he signed with Aston Villa for a fee close to £1.4m, and assumed a regular starting role, although he was frequently injured, being out for two seasons recovering from a serious ankle injury.
[10] However, in Portugal, his problem with injuries remained; on 22 January, just six days after arriving, he sustained a sprain in his right hock with rupture of the joint capsule of his knee, being sidelined for two months.
[11] He finally made his debut on a 3–0 home loss against Boavista on 14 March 1999, and played in three more games, scoring one goal, before being sidelined again on late April, due to a pubalgia.
[12][13] Spending the entire summer recovering from injury, he was put on the transfer list by Jupp Heynckes, so he made a move to his boyhood team West Ham United on 5 October 1999 for £1.2m.