Richardson began his career with the Leewards Islands in 1982 as an opener and after his second season he was called up by the West Indies to tour India in the 1983-84 season. Richardson joined a successful West Indies Test team captained by Clive Lloyd batting in the middle order. He was a flamboyant batsman and superb player of fast bowling. He was famous for his wide-brimmed maroon hat which he wore in preference to a helmet against even the fastest bowlers.
After Viv Richards's Test match retirement, Richie took on the mantle as the captain of the West Indies. He captained the team 24 times winning 11 matches. In the 4 years of his captaincy, the West Indies only lost one series — versus Australia in 1995 which was the West Indies' first series defeat since 1980. Under his captaincy, Curtly Ambrose and Courtney Walsh led the bowling attack and Brian Lara emerged as a world-class batsman.
Richardson played 86 Test matches until 1995 scoring 5,949 runs and 16 centuries. He was very successful against Australia, hitting 9 centuries against them, and scored his highest score of 194 against India in Guyana in 1989. He also played 224 One Day Internationals including 3 World Cups. Richardson's last international was the 1996 World Cup semi-final defeat against Australia, after which he resigned the position of captain.
After his retirement from international cricket, Richardson became the first high-profile signing by the English all-star club cricket team Lashings World XI, and is the current captain of the team. He also plays bass guitar in reggae band Big Bad Dread and The Baldhead alongside Curtly Ambrose.