Born in Leeds, the son of a Co-op butcher, Bennett attended 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 was accepted by Exeter College, Oxford University and went on to take an first-class degree in history. While at Oxford he performed comedy with a number of future successful actors in the Oxford Revue. He was to remain at Oxford for several years researching and teaching Medieval History before deciding 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 that he looked like one.


Album of "Beyond the Fringe" Published by EMI in 1996

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. After the Festival, the show continued in London and New York. He also appeared in My Father Knew Lloyd George. Bennett's first stage play, Forty Years On, was produced in 1968. Many television, stage and radio plays followed, along with screenplays, short stories, novellas, a large body of non-fictional prose and broadcasting, and many appearances as an actor. The recordings of Bennett's highly regarded 1966 television comedy sketch series On the Margin are notorious for having been erased.
Bennett's lugubrious yet expressive voice (which still bears a strong and distinctive Leeds accent) and the sharp humour and evident humanity of his writing have made his readings of his own work (especially his autobiographical writing) very popular. His readings of the Winnie the Pooh stories are also widely enjoyed.
Many of Bennett's characters are unfortunate and downtrodden, or meek and overlooked. Life has brought them to an impasse, or else passed them by altogether. In many cases they have met with disappointment in the realm of sex and intimate relationships, largely through tentativeness and a failure to connect with others.
Bennett is both unsparing and compassionate in laying bare his characters' frailties. This can be seen in his television plays for LWT in the late 1970s and the BBC in the early 1980s, and in the 1987 Talking Heads series of monologues for television which were later performed at the Comedy Theatre in London in 1992. This was a sextet of poignantly comic pieces, each of which depicted several stages in the character's decline from an initial state of denial or ignorance of their predicament, through a slow realization of the hopelessness of their situation, and progressing to a bleak or ambiguous conclusion. A second set of six Talking Heads pieces followed a decade later.
In his 2005 prose collection Untold Stories Bennett has written candidly and movingly of the mental illness that afflicted his mother and other family members. Much of his work draws on his Leeds background and while he is celebrated for his acute observations of a particular type of northern speech ("It'll take more than Dairy Box to banish memories of Pearl Harbor"), the range and daring of his work is often undervalued – his television play The Old Crowd, for example includes shots of the director and technical crew, while his stage play The Lady in the Van includes two characters named Alan Bennett. The Lady in the Van was based on his experiences with a tramp called Miss Shepherd who lived on Bennett's driveway in a dilapidated van for fifteen years.
In 1994 Bennett adapted his popular and much-praised 1991 play The Madness of George III for the cinema as The Madness of King George. The film received four Academy Award nominations, including nominations for Bennett's writing and the performances of Nigel Hawthorne and Helen Mirren). It won the award for best art direction.
Bennett's critically-acclaimed The History Boys won three Olivier Awards in February 2005, for Best New Play, Best Actor (Richard Griffiths), and Best Direction (Nicholas Hytner), having previously won Critics' Circle and Evening Standard Awards for Best Actor and Best Play. Bennett himself received an Olivier Award for Outstanding Contribution to British Theatre..
The History Boys also went on to win six Tony Awards on Broadway, including best play, best performance by a leading actor in a play (Richard Griffiths), best performance by a featured actress in a play Frances de la Tour, and best direction of a play (Nicholas Hytner).
A film version of The History Boys was released in the UK on October 13, 2006. Bennett discussed the play and its themes in an interview interview on stv.tv.
Bennett refused an honorary doctorate from Oxford University in 1998, in protest of its accepting funding for a named chair in honor of press baron Rupert Murdoch. He also declined a CBE in 1988 and a knighthood in 1996. Despite refusing an honorary doctorate from his old university, Bennett was made an Honorary Fellow of Exeter College, Oxford in 1987. He was also awarded a D.Litt by the University of Leeds in 1990.
In September 2005, Bennett revealed that, in 1997, he had undergone treatment for cancer, and described the illness as a "bore". His chances of survival were given as being "much less" than 50%. He began Untold Stories (published 2005) thinking it would be published posthumously. In the event his cancer went into remission. In the autobiographical sketches which form a large part of the book Bennett writes openly for the first time about his homosexuality (Bennett has had relationships with women as well, although this is only touched upon in Untold Stories). Previously Bennett had referred to questions about his sexuality as being like asking a man dying of thirst to choose between Evian or Perrier mineral water.
Bennett earned Honorary Membership of The Coterie in the 2007 membership list.
Bennett has lived in London's Camden Town for thirty years, and shares his house with his partner of fourteen years, Rupert Thomas.