Sometimes called the father of the modern obituary, Massingberd was most revered for his work as obituaries editor for The Daily Telegraph of London from 1986 to 1994, during which time he drastically altered the style of the modern British obituary from a dry recital of biographical data to an often sly, witty, yet deadpan narrative on the deceased person's life.
Massingberd was born Hugh John Montgomery at Cookham Dean, Berkshire, England, in 1946. His father, John Montgomery, was a member of the Colonial Service. His mother, Marsali Seal de Winlaw, was a schoolmistress who married John Montgomery after her first husband Roger de Winton Kelsall Winlaw died in 1942 in the service of the Royal Air Force. Hugh was the first child of her union with John Montgomery. Through his father, Massingberd was the great great grandson of Charlotte Langton (née Wedgwood), she being sister of Emma Darwin (Charles Darwin's wife) and granddaughter of the potter and philanthropist Josiah Wedgwood I.
His boyhood enthusiasms included cricket, literature, horse-racing and showbusiness.
John and Hugh Montgomery, in order to inherit the estate of John's aunt and uncle (he was the son of Diana's sister and Archibald's brother) Diana née Langton Massingberd and her husband Field Marshal Sir Archibald Montgomery-Massingberd of Gunby, East Lindsey, Lincolnshire, were obliged to hyphenate their surnames, becoming in 1963, John Montgomery-Massingberd and Hugh John Montgomery-Massingberd. Hugh later dropped his original surname in 1992, and was known simply as Hugh Massingberd.
He was extremely proud of his reputation as a gourmand and a trencherman, posing at one time for a portrait with a garland of sausages. Often retold was the story of his having eaten the largest breakfast ever served at the Connaught Hotel in 1972; the head waiter reported to his table that the previous record holder had been King Farouk I of Egypt.
Massingberd was known for his wit in his private life as well as in his public life as a writer. A friend once asked him, during one of Massingberd's low moods, what would cheer him up; after some thought, Massingberd replied, "To sing patriotic songs in drag before an appreciative audience."
Massingberd was diagnosed with cancer in 2004, and died on Christmas Day, 2007, five days before his 61st birthday.
After leaving school at Harrow, Massingberd discarded initial plans to attend the University of Cambridge, instead choosing to work as a law clerk. He then moved to an assistantship at Burke's Peerage, the historical and genealogical listing of the United Kingdom's titled families. He was chief editor of Burke's Peerage from 1971 to 1983. Massingberd then worked as a freelance columnist for The Spectator and The Field until assuming his position with The Daily Telegraph in 1986.
As obituaries editor at The Daily Telegraph, Massingberd entirely altered the reverential but otherwise factual style of the obituary. He replaced the traditional tone of respect with one of adroitly subtle humor, and quickly drew readership. The New York Times reported that "cataclysmic understatement and carefully coded euphemism were the stylistic hallmarks of his page." He said his inspiration was Roy Dotrice's performance in 1969 in Brief Lives in the West End in which Dotrice, after reading out a "dull, formulaic entry about a barrister, shut the book with a 'Pshaw' and turned to the audience to say" 'He got more by his prick than his practice'." Massingberd said that he resolved then "to dedicate myself to chronicling what people were really like through informal anecdote, description and character sketch". He felt it was possible to give a true assessment of the subject and to present "a sympathetic acceptance, even celebration, of someone's foibles and faults".
Massingberd famously referred to the 6th Earl of Carnarvon, a deceased man with a habit of indecent exposure, as "an uncompromisingly direct ladies' man." He termed the late maverick Dead Sea Scrolls academician John Allegro, who later argued for Judeo-Christian cultism regarding mushrooms and sexual intercourse, the "Liberace of biblical scholarship."
Massingberd's sphere of influence was large. Following his editorship tenure, obituaries in not only The Daily Telegraph but in many other British publications, such as The Times of London, took on the dryly impish character for which his writings had become famous. He wrote over 30 books, many of them on the British aristocracy and the great houses of England, Scotland and Ireland, reviewed books for The Spectator, Country Life and the Telegraph, and also wrote a play based on the diaries of James Lees-Milne.
After his resignation, Massingberd continued to write, authoring book reviews for The Daily Telegraph as well as several theatrical works. When one of his theatre pieces, Love and Art, was produced at the Wallace Collection in 2005, Massingberd played one of the roles on stage. Massingberd left behind a considerable body of written work, both as author and as editor.
- The Monarchy (1979)
- The British Aristocracy (with Mark Bence-Jones, 1979)
- The London Ritz (with David Watkin, 1980)
- The Country Life Book of Royal Palaces, Castles and Homes (with Patrick Montague-Smith, 1981)
- Diana: The Princess of Wales (1982)
- Heritage of Royal Britain (1983)
- Royal Palaces of Europe (1984)
- Blenheim Revisited (1985)
- Her Majesty The Queen (1986)
- Debrett's Great British Families (1987)
- The Field Book of Country Houses and their Owners: Family Seats of the British Isles (1988)
- Queen Elizabeth The Queen Mother (1999)
- Daydream Believer: Confessions of a Hero-Worshipper (2001; autobiographical)
- Ancestral Voices (2002)
- Love and Art (2005)
With Christopher Simon Sykes:
- Great Houses of England and Wales (1994)
- Great Houses of Scotland (1997)
- Great Houses of Ireland (1999)
- English Manor Houses (2001)
- Burke's Peerage, Baronetage & Knightage (1971-1983; assistant editor, 1968-1971)
- Burke's Guide to the Royal Family (1973)
- Burke's Irish Family Records (1976)
- Burke's Royal Families of the World, Vols. 1 and 2 (1977 and 1980)
- Burke's Guide to Country Houses, Vols. 1-3 (1978, 1980 and 1981)
- The Daily Telegraph Record of the Second World War (1989)
- A Guide to the Country Houses of the North-West (1991)
- The Disintegration of a Heritage: Country Houses and their Collections 1979-1992 (1993)
- The Daily Telegraph Book of Obituaries, Vols. 1-6
- The Very Best of the Daily Telegraph Books of Obituaries (2001)
- McGinness, Mark (2008) "Father of the modern obit: Hugh Massingberd (1946-2007)", The Sydney Morning Herald, Weekend Edition, 5-6 January 2008, p. 56
- Vickers, Hugo (January 2011). "Massingberd, Hugh John Montgomery- (1946–2007)". Oxford Dictionary of National Biography. Oxford University Press. doi:10.1093/ref:odnb/99301. Retrieved 9 December 2011.
- Obituary, Daily Telegraph, 27 December, 2007
- Brown, Craig (27 December 2007). "Hugh Massingberd, obituaries master, dies". The Daily Telegraph (London).
- Fox, Margalit (30 December 2007). "Hugh Massingberd, 60, Laureate for the Departed, Dies". The New York Times (New York). Retrieved 29 September 2013.
- cited by McGinness, Mark (2008) "Father of the modern obit: Hugh Massingberd (1946-2007)", The Sydney Morning Herald, Weekend Edition, 5-6 January 2008, p. 56
- "My Mentor: Andrew McKie On Hugh Massingberd". The Independent (London). 23 January 2006.
- Obituary for Hugh Massingberd, The Daily Telegraph, 12 December 2007
- "Hugh Massingberd, obituaries master, dies", The Daily Telegraph, 12 December 2007
- "Hugh Massingberd, 60, Laureate for the Departed, Dies", New York Times, December 30, 2007
- Article on Massingberd, The Guardian
- Obituary for Massingberd, The Times (UK)