In 1958 he first appeared on record as the lead vocalist with The Boss-Tones, singing "Mope-Itty Mope". Barry also was a member of the singing group, The Dovells from 1957 to 1963, before quitting to go solo.
As a predominately blue-eyed soul singer, he recorded two hits in 1965 and 1966 for Decca Records: "1-2-3", and "Like A Baby", both of which made the Top Ten of the UK Singles Chart. Both songs were part composed by Barry and Dave White, one of the original Juniors from Danny & the Juniors.
When the hits dried up, Barry continued performing his entertaining stage act, and later moved into songwriting and production work with WMOT Productions.