Berry was born in Rostrup, Germany. His father was a serviceman from Jamaica while his mother was Welsh. The Berry family moved to Blackpool, England soon after his birth. Whilst living in Blackpool Berry started playing football and played for the same youth club as the nephew of former Liverpool player Alun Evans who after watching Berry, Evans recommended him for a trial at Wolverhampton Wanderers. His trial was successful and they offered him a contract, Berry could not wait to leave school and signed the day after completing his 'O' levels in 1973. He turned professional on his 18th birthday and made his debut away at Chelsea on 7 May 1977. In 1979, he played in a benefit match for West Bromwich Albion player Len Cantello, that saw a team of white players play against a team of black players. Berry became first choice throughout the next few years, winning the fans' player of the year award in 1979 and the 1980 League Cup, when Wolves beat reigning European champions Nottingham Forest 1–0 at Wembley. The club suffered relegation though in 1981–82 and Berry joined Stoke City.
Stoke City
Berry joined Stoke City on a free transfer in July 1982 joining up with Richie Barker who had previously worked as assistant manager at Wolves. Berry was a good header of the ball and while he lacked technical skill he made up for it with his determination and commitment which combined with his distinctive afro style haircut meant Berry was well on his way to becoming a cult hero. With Stoke bottom of the First Division in December 1983 Barker was sacked and caretaker manager Bill Asprey banished Berry to the youth team as he sought to restore defensive stability to the team which had conceded 33 goals in the first 17 matches. Berry received no explanation for this public humiliation and the pair never spoke again. However typical of his character, Berry returned to the side after a loan spell at Doncaster Rovers and a period of inactivity where he trained alone in Portugal, he did make a return to the first team but Stoke were relegated in 1984–85 with a then record low points tally of 17. New manager Mick Mills appointed Berry as captain and formed a good defensive partnership with Steve Bould and the pair nearly helped Stoke reach the play-offs in 1986–87. He became one of Stoke's brightest players in what was a pretty dull period for the club and was given a Testimonial match against Port Vale in August 1990 after making 267 appearances for the club scoring 29 goals.
Later career
He was give a free transfer to Peterborough United where he spent the 1990–91 season before moving to Preston North End however his ageing legs could not cope with Deepdale's plastic pitch and he left for Aldershot. They were forced to close down mid-season due to financial problems and Berry decided to retire.
After retiring from playing, Berry gained a business degree and became the senior commercial executive at the Professional Footballers' Association. He is also president of the Stoke City Southern Supporters Club.