After training at two art colleges, Hoffnung taught for a few years, and then turned to drawing, on the staff of English and American publications, and later as a freelance.

[8] In the words of his biographer Richard Ingrams, Hoffnung developed a distinctive style which owed something to the German illustrator Wilhelm Busch.

Examples include the drawing of a musician being devoured by the serpent he is trying to play;[10] another shows a singer whose waistcoat buttons are control knobs labelled On/off, ppp/fff, Wobble, and Sobs.

[1] Probably the best-known example of Hoffnung as a humorous speaker is an account of a bricklayer's misfortunes when lowering some bricks in a barrel from the top of a building.

It was published in Reader's Digest in 1940 as a letter from a naval officer who had supposedly received it from an enlisted man explaining his late return from leave.

[1] The tale was later cast into music as The Sick Note by Pat Cooksey, versions of which were popularized by several other performers including Seán Cannon and The Dubliners.

Among Hoffnung's other well-known subjects were his supposedly helpful advice to tourists in London ("Have you tried the famous echo in the Reading Room of the British Museum?")

[22] In 1952 Hoffnung married Annetta Perceval, née Bennett; they had two children,[23] Ben (Benedict) and Emily who became, respectively, a timpanist[24] and a sculptor.

According to a biographical sketch by Joel Marks, first published in Essays in Arts and Sciences (University of New Haven, Volume XXI, 10/1992), "Hoffnung's outlook on race relations, homosexuality, nuclear disarmament, the treatment of animals (especially hunting) and, for that matter, the music of Bartók and Schoenberg [was] liberal and impassioned."

A week before he died he took part in a show at the Festival Hall in aid of the Campaign for Nuclear Disarmament, along with Peggy Ashcroft, Benjamin Britten, C. Day Lewis, Michael Redgrave and others.

[26] Hoffnung collapsed at his home on 25 September 1959, and died of a cerebral haemorrhage three days later in New End Hospital in Hampstead at the age of thirty-four.

[1] The obituarist in The Times concluded: Hoffnung was among other things an artist, a musician, a linguist, a raconteur, a Quaker, a bon viveur, a prison visitor and a mime.

A memorial tribute, O Rare Hoffnung was published in 1960 and included contributions from Malcolm Arnold, John Dankworth, William Mann, Ian Messiter, Gerald Priestland, Donald Swann and nineteen others.

The above six volumes were reissued as a uniform set in 2002 with forewords by Sir Simon Rattle, Peter Ustinov, Ronald Searle, Harry Enfield, Ian Hislop, and Hoffnung's daughter, Emily.