Born in Leeds, Bennett was schooled at Leeds Modern School (a state grammar school), learned Russian at the Joint Services School for Linguists during his National Service, and gained a place at Cambridge University. However, having spent time in Cambridge during national service, and partly wishing to follow the object of his unrequited love, he decided to apply for a scholarship at Oxford University. He went on to take a first-class degree in history from Exeter College, Oxford. He was to remain at Oxford for several years studying Medieval History before realising he was not cut out to be an academic.
He claims that as an adolescent he assumed he would grow up to be a Church of England clergyman, for no better reason than he looked like one.
In August 1960, Bennett, along with Dudley Moore, Jonathan Miller, and Peter Cook, achieved instant fame by appearing at the Edinburgh Festival in the satirical revue Beyond the Fringe.
