Webb grew up in affluent Pasadena, California. He attended Midland School in Los Olivos, California and graduated from Williams College in 1961. He declined an inheritance from his father, a wealthy doctor [1].

Webb lived for several years in Hastings-on-Hudson, New York.

As of 2006, Webb has 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 [2]. Fred is an artist and her work includes illustrations for Webb's 2002 novel New Cardiff. The couple have two sons, one of whom is now a performance artist who once cooked and ate a copy of The Graduate with cranberry sauce [3].

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 [4] or against the US's lack of marriage rights for gays [5]. 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 [6]. They currently live in Hove, East Sussex, England.

Webb's first and still most famous novel was published in 1963. Allegedly based upon his affair with an older, wealthy, beautiful and married Pasadena socialite, that created quite a stir in conservative Pasadena, and written in the poolside bar of the Pasadena Huntington Hotel, the story epitomized the social tensions of the 1960s. As with much of his work, it was perhaps most immediately notable for its flawlessly pitched dialogue, its wry (if not sly) humor, and its evocative and communicative understatement. The character of "archetypal seductive older woman" Mrs. Robinson has probably 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[7]. 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. Although the book was one of the most telling American novels of the 1960s, and mainly through the film one of the most quoted, it is generally excluded from the literary canon of the period, as are his other books.

In April 2006 it was reported that Webb had written a sequel to The Graduate, entitled 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. [8]

Extracts of Home School were printed in The Times on May 2, 2006. [9] 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.[10]

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 some £1,600 [11]. 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[12], who has been clinically depressed since suffering a nervous breakdown in 2001. [13]

In May 2006, however, The Times reported [14] 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 27 May 2007 The Sunday Telegraph published a story [15] 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 9780312376307.