Sir Humphrey won a classical scholarship to Winchester College before reading Classics at Baillie College, Oxford (a possible reference or allusion to Balliol College, Oxford). After National Service in the Army Education Corps he entered the Civil Service. From 1950 to 1956 he was the Regional Contracts Officer, an assistant principal in the Scottish Office, on secondment from the War Office (where he was responsible for a serious mistake that was revealed in "The Skeleton in the Cupboard"). In 1964 he was brought into the newly-formed Department of Administrative Affairs, where he has worked until his appointment as Cabinet Secretary. He is recommended for the KBE early on in the series in "The Official Visit".
Sir Humphrey represents, in many ways, the perfect technocrat. He is pompous, arrogant and elitist, and regards his less-well-educated minister with some contempt. He frequently uses both his mastery of the English language and even his superb grasp of Latin and Greek grammar to perplex his political master and to obscure relevant issues under discussion. However, his habit of using language as a tool of confusion and obstruction is so deeply ingrained that he is sometimes unable to speak clearly and directly even in circumstances in which he honestly wishes to make himself clearly understood. He genuinely believes that the Civil Service knows what the average person needs and is the most qualified body to run the country, the joke being that not only is Sir Humphrey, an Oxford-educated Civil Servant, quite out of touch with the average person but also that the Civil Service identifies whatever is 'best for Britain' as being 'best for the Civil Service'. Jim Hacker, on the other hand, tends to regard what is best for Britain as being whatever is best for his political party or his own chances of re-election. As a result, Sir Humphrey and Hacker often clash.
He still holds women to be the fairer sex, and is thus overly courteous, frequently addressing them as "Dear lady". Like Hacker, Sir Humphrey enjoys the finer things in life, and is regularly seen drinking sherry and dining at fine establishments, often with his fellow civil servant Sir Arnold Robinson, who was Cabinet Secretary throughout Yes Minister. Sir Humphrey is also on the board of governors of the National Theatre and attends many of the gala nights of the Royal Opera House. His interests also extend to cricket, art and theatre.
According to the foreword (dated 2019), of the book The Complete Yes Minister: The Diaries of a Cabinet Minister by the Rt. Hon. James Hacker MP, a novelisation of the series, he spent his last days in St Dympna's Hospital for the Elderly Deranged, after the "advancing years, without in any way impairing his verbal fluency, disengaged the operation of his mind from the content of his speech." This contradicts the date of death given in Politico's Book of the Dead.
In a Radio Times interview to promote the first series of Yes, Prime Minister, Nigel Hawthorne commented, "He's raving mad of course. Obsessive about his job. He'd do anything to keep control. In fact, he does go mad in one episode. Quite mad.
A spoof obituary for Sir Humphrey appears in Politico's Book of the Dead, written by his creators, Antony Jay and Jonathan Lynn. This is the source for some biographical details above, including the dates of birth and death, which he shares with Nigel Hawthorne, the actor who portrayed him.
Sir Humphrey was voted the 45th greatest comedy character in Channel 4's 2007 "The World's Greatest Comedy Characters" poll. He was also voted 31st in a poll of "100 Greatest TV Characters", also on Channel 4.
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