Cowling was born in Norwood, South London, to a lower middle-class family. His family then moved to Streatham, where Cowling attended an LCC elementary school, and from 1937 the Battersea Grammar School. When the Second World War started in 1939 the school moved to Worthing and then from 1940 to Hertford where Cowling attended sixth-form.
In 1943 Cowling won a scholarship to Jesus College, Cambridge, but was called up for military service in September 1944, where he joined the Queen's Royal Regiment. In 1945, after training and serving in a holding battalion, he was sent to Bangalore as an Officer Cadet.
In 1946 Cowling was attached to the Kumaon regiment and the next year-and-a-half he travelled to Agra, Razmak on the North-West Frontier and Assam. As independence for India neared in 1947, Cowling was dispatched to Egypt as a camp adjutant to the British HQ there. Cowling was then promoted to captain in Libya. By the end of 1947 Cowling was finally demobilised, and in 1948 he went back to Jesus College to complete his Historical Tripos, where he got a Double First. Cowling later remembered that he fell in love with Cambridge. He toyed with the idea of being ordained and went to college chapel, possessing "a strong polemical Christianity". Of his religion, Cowling later claimed: "I'm not sure of the depth or reality of my religious conviction. It could well be that it was a polemical conviction against liberalism rather than a real conviction of the truth of Christianity...I suppose on a census I would describe myself as a member of the Church of England. If you ask me, do I think I ought to be an Anglican, the answer is that I probably ought to be a Roman Catholic, but I don't see any prospect of that happening...I have a very Protestant mind".
In 1954 Cowling worked at the British Foreign Office for six months at the Jordan department, and in early 1955,
The Times gave him the job of foreign leader-writer, which he held for three years. In 1957 Cowling was invited by the Director of the Conservative Political Centre to write a pamphlet on the Suez Crisis; it was never published however, as the party wanted to move on from Suez as quickly as possible. He stood unsuccessfully for the parliamentary seat of Bassetlaw during the General Election of 1959 for the Conservative Party. Cowling later said that "I enjoyed being a candidate, though it was very hard work and elections are like what I imagine having all your teeth out is like".
In 1961 Cowling was elected a Fellow of Jesus College and Director of Studies in Economics, shortly before the History Faculty appointed him to an Assistant Lectureship. Cowling's first book was
The Nature and Limits of Political Science. Influenced by Michael Oakeshott, this was an attack on political science and political philosophy as it was then taught. Cowling argued that social science's claim to have discovered how people behaved was false because politics was too complex and fluid to be rationalised by theorists and only fully intelligible to politicians.
During six weeks of the summer of 1962 Cowling wrote
Mill and Liberalism, which was published in 1963 and became one of his most contentious books. The book claimed Mill was not as libertarian as he was traditionally portrayed, and that Mill resembled a "moral totalitarian". Dr. Roland Hill reviewed the book in
Philosophical Quarterly (January 1965) and called it "dangerous and unpleasant", with Cowling later remarking that this "was what it was intended to be".
In 1963 he was elected a Fellow to Peterhouse, Cambridge where he advised his students to tackle liberals with "irony, geniality and malice". During the 1960s Cowling campaigned against a sociology course to be introduced at Cambridge, regarding it as a "vehicle for liberal dogma". In November 1966 Cowling was elected as a Conservative councillor on the Cambridgeshire and Isle of Ely County Council in a by-election, which he held until 1970.
He was appointed the literary editor of
The Spectator from 1970—1971, and in the early 1970s he wrote articles of a broadly Powellite nature arguing against the UK being a member of the EEC. Cowling resigned in 1971 when the editor acting in George Gale's absence refused to publish Cowling's protest against his publication of an article by Tony Palmer which suggested that the important question about Princess Anne was whether she was a virgin.
It was on Cowling's suggestion that Paul Smith edited a collection of Lord Salisbury's articles from the Quarterly Review, published in 1972.
In 1977 Margaret Thatcher visited the Cambridge Graduate Conservative Association of Peterhouse where she "cut through the compact subtlety and ‘rational pessimism’ of [Cowling]" and sharply retorted: "We don't want pessimists in our party". In 1978 he ceased to be Director of Studies in Peterhouse, and helped to found the Salisbury Group, a group of conservative thinkers named, on Michael Oakeshott's advice, after Lord Salisbury. In the same year Cowling published
Conservative Essays where he said:
If there is a class war — and there is — it is important that it should be handled with subtlety and skill. ... it is not freedom that Conservatives want; what they want is the sort of freedom that will maintain existing inequalities or restore lost ones.
Cowling was "instrumental" in getting the historian Lord Dacre of Glanton from Oxford to become Master of Peterhouse from 1980 to 1987, though in later years he came to regret supporting Dacre's arrival there. In November 1989 Cowling published his essay on ‘The Sources of the New Right’ in
Encounter which detailed the ideological roots of Thatcherism Britain and became the Preface to the second edition of
Mill and Liberalism in 1990. In 1990 Cowling described himself as "an intellectual Thatcherite, just as I was an intellectual Powellite, and I think it is important that the Conservative party should be in good hands and that it should win elections...I am a warm supporter [of the Thatcher government]". In Cowling's view "Liberalism is essentially the belief that there can be a reconciliation of all difficulties and differences, and since there can't, it is a misleading way to approach politics". He regarded Salman Rushdie's
The Satanic Verses as "a nasty, sneering, free-thinking book...I can understand why the book is offensive and it didn't seem to me to be anything but offensive when I read it. Some thinking Moslems take a view of the nature of religion, and the incompatibility between Islam and liberalism, which runs parallel to what I'm saying in
Mill and Liberalism".
In 1992 Philip Williamson published his book on British politics from 1926 to 1932 and said Cowling "provided the original inspiration" for it.
Cowling retired from the History Faculty of Cambridge in 1988, and from his Fellowship of Peterhouse in 1993. In 1996, in Swansea, Cowling married George Gale's ex-wife Patricia. In 2005 in Swansea, Cowling died after a long illness.
