He was educated at St Christopher School, Letchworth, and Downing College, Cambridge, where he read law and economics. He also edited the university's student newspaper, Varsity (he was the youngest ever Editor up to that time, both in age and in terms of his university career, being only in the second term of his second year). Winner had earlier written a newspaper column, 'Michael Winner's Showbiz Gossip,' in the Kensington Post from the age of 14. The first issue of Showgirl Glamour Revue in 1955 has him writing another film and showbusiness gossip column, "Winner's World". Such jobs allowed him to meet and interview several leading film personalities, including James Stewart and Marlene Dietrich. He also wrote for the New Musical Express.