Born in Newham, London, Charles started his career at Clapton F.C., but first came into notability at Nottingham Forest, when he became a regular alongside Roy Keane, making his debut on 7 November 1987. Due to his colour and skills, he was dubbed "the Brazilian". His manager at Forest, Brian Clough, commented on his dribbling abilities by saying: "When he plays a one-two he goes like a gazelle. It's so effortless that at first it looks as if he's not moving, yet he's 40 yards up the field. In June 1991, he made his debut for England, playing two friendlies, against New Zealand on 8 June and Malaysia on 12 June. Only a few days earlier, Charles was famously fouled by Paul Gascoigne in the 1991 FA Cup Final. This was the challenge that caused Gascoigne's cruciate ligaments to tear, forcing him out of the game for several months. On 29 March 1992, he made the squad that won the Full Members Cup against Southampton.