Booker began writing jazz reviews for "The Daily Telegraph" while at university. From 1961 to 1964, he wrote about jazz for "The Sunday Telegraph" as well. His contributions included a positive account of a concert given by the pianist Erroll Garner, which did not happen; it was a late cancellation. In 1962, he became the resident political scriptwriter on the BBC satire show "That Was The Week That Was", notably contributing sketches on Home Secretary Henry Brooke and Prime Minister Sir Alec Douglas-Home which have often been cited as examples of the programme's outspoken style.