O'Brien's first tryst with television and quizzing happened in 1966, when he visited England and was exposed to the pub quiz culture. He came back and organised the first-ever open quiz in the country in 1967, at Christ the King Church Parish Hall in Kolkata.
The audience for the quiz show was said to be around 40. But by the time O'Brien, 82, died on Friday, he would have inspired generations.
O'Brien's contribution to society doesn't just rest with quizzing. He was also an educationist. A Master of Arts in English Literature from Calcutta University, O'Brien went on to teach English at St Xavier's College. He then joined Oxford University Press, India, where he retired after a 38-year stint as its managing director. He was also the chairman of the Council for the Indian School Certificate Examinations.
As son Derek, also the chief national spokesperson for the Trinamool Congress and Rajya Sabha MP, broke the news of his father's demise on Twitter, many recalled proudly how their marksheets bore O'Brien's signature.
He was a three-time nominated Anglo-Indian member in the West Bengal Legislative Assembly and elected to the Lok Sabha in 1996.
O'Brien is survived by his wife Joyce and three sons, Derek, Andy and Barry, who have carrying forward his quizzing legacy.
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