Barry joined Aston Villa from Brighton and Hove Albion as a trainee in 1997, along with Michael Standing. The move was controversial, for the Brighton board had demanded £2.5 million for the two players; the Football Association's transfer tribunal panel came up with a deal which would have seen Brighton make £2.4 million in the event of Barry and Standing making international appearances for England, as well as sell-on clauses. He played his first match for Villa on 2 May 1998, a 3–1 win at Sheffield Wednesday, as a 49th-minute substitute for Ian Taylor. On 24 April 1999, on at half time for the injured Dion Dublin, he finished Steve Stone's cross 12 minutes later for his first professional goal, concluding a 2–0 win over Nottingham Forest at Villa Park. He started in the 2000 FA Cup Final at the old Wembley Stadium, which Villa lost 1–0 to Chelsea. In August 2001, he featured as Villa defeated FC Basel 5–2 on aggregate in the final of the 2001 UEFA Intertoto Cup.