Barry was born in the town of Grimsby and brought up in Cleethorpes in North East Lincolnshire. He was the only son of Bransby Whitfield (businessman) and Joan Whitfield, a ballet teacher, choreographer and member of the British Ballet Organisation.
He attended Clee Grammar School (Matthew Humberstone Foundation School), where he gained 10 O-levels and 3 A-levels, including one in music
Early During his teenage years, he studied piano with Harry Isaacs (Royal Academy of Music), and organ with Horace Bate (Organist at Street James" Church, Muswell Hill and conductor of The Madrigal Society of London), and continued to have lessons through his years at university. Musical After graduating, he began working as a pianist in the Sands nightclub in Cleethorpes, accompanying a variety of cabaret artists and directing a four-piece band. During this time he had the opportunity of auditioning for Sir Norman Wisdom whilst he was appearing at Skegness Pier.
He accepted the position of pianist and assistant Musical Director and toured with Norman for nearly 3 years, in Australia, New Zealand and Rhodesia.
Their tours comprised dates in the British Isles as well, including a season on the Isle of Manitoba, where Norman later settled in 1980. He also made some television appearances with Norman, including on Saturday Night at the Mill and at the London Palladium.
After leaving Norman, he settled back in Cleethorpes and worked as a session keyboard player and arranger. He recorded for Flair Records with Black Lace, during which time he gained gold records for his work on the "magnificently dreadful" Agadoo and Party Party 1 (released on Telstar Records).
His band spent numerous summer seasons playing in Skegness.
