Webb was born in San Francisco, California. He grew up in affluent Pasadena, California. He attended Chandler School, Midland School in Los Olivos, California, and graduated from Williams College in 1961. He declined an inheritance from his father, a wealthy doctor.
Webb lived for several years in Hastings-on-Hudson, New York.
As of 2006, Webb had been with his long-term partner Eve for more than 40 years. Eve shaves her head and calls herself "Fred" in solidarity with a Californian support group called Fred, for men who have low self-esteem. Fred is an artist and her work includes illustrations for Webb's 2002 novel New Cardiff. The couple has two sons, one of whom is now a performance artist who once cooked and ate a copy of The Graduate with cranberry sauce.
The Webbs removed their children from school so that they could tutor them at home. This was an illegal act in California at the time, and to evade the authorities they fled the state; at one point they managed a nudist camp in New Jersey. They also divorced – accounts vary as to why (it was not due to personal differences), either in protest against the institution of marriage, or against the US's lack of marriage rights for gays. They sold their wedding presents back to their guests, and having given away four houses in succession lived on the breadline, taking menial jobs as cleaners, cooks and fruit-pickers, working at K-Mart and living in a shack. They currently live in Eastbourne, East Sussex, England.
Webb's first and most famous novel was published in 1963, foreshadowing many of the social tensions of the 1960s which the book would come to represent. Through this novel, the character of "archetypal seductive older woman" Mrs. Robinson has found a permanent niche in American cultural history.
The novel was made into a hugely successful film in 1967 by Mike Nichols. Webb has stated that he never felt comfortable with the attention the movie brought him because he felt it distracted from his status as a serious artist.
Webb sold the film rights for a one-off payment reported to be $20,000. He was rarely associated with the movie's publicity and not particularly with the growth of its reputation. Buck Henry and Calder Willingham, the script writers, assumed much of the credit for the work despite taking most of the dialogue directly from the book.
During the movie's enormous success, the producer, Joseph E. Levine, offered Webb token recognition by an additional compensation of $10,000.
In April 2006 it was reported that Webb had written a sequel to The Graduate, titled Home School but refused to publish it in its entirety because of a copyright loophole. When he sold the film rights to The Graduate in the 1960s, Webb also surrendered the film rights to any sequels. If he were to publish Home School, Canal+, the French media company that now owns the rights to The Graduate, would be able to adapt it for the screen without his permission.
Extracts of Home School were printed in The Times on May 2, 2006. Webb also told the newspaper that there was a possibility he would find a publisher for the full text, provided he could retrieve the film rights using French intellectual property law.
At the same time as this news broke, Webb and his wife were also widely reported to be in such financial hardship that they were facing eviction from their home, owing rent of £1,600. Webb said to The Times that although his writing had proceeded, "the selling [of his books] hasn't" because he spends most of his time caring for Fred, who has been clinically depressed since suffering a nervous breakdown in 2001.
In May 2006 The Times reported that Webb had signed a publishing deal for Home School with Random House which would enable him to clear almost all his debts and instruct the French lawyers to attempt to retrieve his rights. On May 27, 2007 The Sunday Telegraph published a story that the novel was to be published in June 2007 and reported Webb having moved to Eastbourne.
Home School was published by Hutchinson in June 2007. ISBN 978-0-09-179565-8 and by St. Martin's Press, January 2008, ISBN 978-0-312-37630-7.
Among Webb's other work, the novel The Marriage of a Young Stockbroker was made into a feature film with Richard Benjamin and Joanna Shimkus, and his novel New Cardiff was made into a film entitled Hope Springs.
It was reported in 1992 by The Washington Post that Webb was working on a new book entitled Lies. As of 2013 the existence of the book has not been confirmed.The Graduate (1963)
Love, Roger (1969)
The Marriage of a Young Stockbroker (1970)
Orphans and Other Children (1975)
The Abolitionist of Clark Gable Place (1976)
New Cardiff (2002)
Home School (2007)