Jackson was born on 6 September 1879 in
Kings Norton, Worcestershire the son of George and Jane ( Spreadborough) Jackson. The Jacksons were a prominent and wealthy family of merchant grocers. His father, George, was a prominent businessman who was passionate about the theatre, reportedly naming his son for renowned British stage actor
Barry Sullivan. From a young age, Jackson was exposed to the theatre and to the arts, from school where he was privately educated, to regularly attending the theatre, opera and ballet. The young Jackson saw his first Shakespeare production,
The Taming of the Shrew, performed by the
Frank Benson Company when he was ten years old. In his teenage years, he travelled around Europe, visiting Greece and Italy, living in Geneva for eighteen months where he studied French and learnt to paint. He desired to become an artist, but his father persuaded him to take a job in the architect's office of Frank Osborn in Birmingham, beginning working there in 1897. His time there did now inspire him creativity, as he had already turned his focus to writing and performing plays with a group of his friends. Along with his friends they christened the company, The Pilgrim Players. This was to be the amateur foundations for the future Birmingham Repertory Theatre Company. Jackson alongside his friends,
John Drinkwater, H S Milligan and C. R. Dawes had been performing their own productions at the Jackson's family home of the Grange in Moseley, from around 1902 to family and friends. Their first public appearance took place on 2 October 1907 at the Mission Hall in Inge Street. The following year performances moved to the Edgbaston Assembly Rooms. The company was increasingly gaining in reputation and popularity in the city. Jackson was confident in the potential that the dedicated company possessed. He employed Drinkwater as the company Secretary from 1909, and from 1911, all of the Players were paid. At the start of 1912, Jackson began to identify and develop plans to build a permanent theatre for the expanding company. He had clear ideas about the design which he discussed with the architect
S. N. Cooke, who had studied with Jackson at the School of Art. ==Birmingham Repertory Theatre==