Osbert Lancaster: A knight of laughter who satirised a stuffy nation

Few professions have done more to illuminate Karl Marx's dictum on history repeating itself – the first time as tragedy, the second as farce – than that of cartoonists.

Sketches first pencilled decades ago often accrue prescience with age, passing comment on the travails of today as perceptively as they did on the idiosyncrasies of yesteryear. In some cases, they seem more fitting for publication now than when first produced. Such can be said of those that issued from the hand of Sir Osbert Lancaster, pictured below, late stalwart of the then all-powerful Daily Express who would be knighted for his pioneering cartoons.

In a career spanning four decades, Sir Osbert's pencil proved one of the mightiest swords in all Fleet Street. At times, his cartoons would feature a conversation between two characters, Maudie and William Littlehampton, the archetypal Middle England couple. At other times he cut into the reputation of the rich and powerful, clinically exposing inadequacies and pretensions. His work, to be celebrated in a major exhibition to mark his centenary this year, continues to inspire contemporary cartoonists, because though times change, themes remain.

A constant, sardonic wit emanates from Sir Osbert's creations even today. A cartoon from 1948 predicts the forthcoming London Olympics would lead to deterioration in international relations. Another, from 1958, voices anxiety over economic gloom and the threat of recession, while one from 1969 pokes fun at a prime minister in need of an image makeover. The tone of each drawing, crafted with thin pencil lines that exaggerate even the mildest eccentricity, is acerbic.

Born in Chelsea a century ago today Sir Osbert's eventful, peripatetic life exuded the quintessentially middle-class Englishness that his cartoons satirised. He was dispatched to Charterhouse boarding school shortly before his eleventh birthday. From there, he would go up to Lincoln College, Oxford, where he read English and befriended the poet John Betjeman, winning admiration all the while for his contribution to Cherwell, the university newspaper. He left with a fourth-class degree, and later flunked his Bar exams.

The Bar's loss would be Fleet Street's gain. After working with Betjeman on the august Architectural Review, Sir Osbert joined the Daily Express, for whom he would go on to draw over 10,000 cartoons, in 1939. The intervention of war led to his working first for the press censorship bureau and then in Greece, as a press attaché for the Foreign Office. In 1951 he worked for John Piper, the English painter, before designing the stage for several productions at Sadler's Wells and Glyndebourne. All the while he was churning out books, many of them about architectural and aesthetic traditions in Littlehampton, West Sussex, where he lived. At the Express, he pioneered the idea of a front page cartoon strip in a sequence of three frames, later adopted with such effectiveness by the Daily Telegraph's "Matt".

Described by Anthony Powell as one of England's finest artists, he became a fixture in gossip columns and society magazines, counting among his friends Benjamin Britten, Evelyn Waugh, and Max Beerbohm. But his fame was matched by a genuine reverence among fellow scribblers, few of whom have any qualms describing Sir Osbert as the most distinguished British cartoonist of his, or any other, generation.

"Even if Sir Osbert Lancaster had not been blessed with a timeless sense of humour, he would remain the finest pocket cartoonist this country has ever produced," says Barry Fantoni, a cartoonist for Private Eye. "Not only could Sir Osbert draw properly, he had an unerring eye for fashion and architecture that made his small drawings a pleasure, even in the inconceivable event that you did not find his caption funny. I buy his little collections from second-hand book shops on a regular basis. They are, for me, worth any number of written social histories. If I want a quick review of, say, the Sixties, a Sir Osbert annual is where I start. His drawings alone tell the story, and tell it with wit and flair."

Martin Rowson, cartoonist and chairman of the British Cartoonists' Association, says: "The great thing about Osbert is that although he appealed to the establishment, he was in fact deeply subversive. His best-known character, Maudy Littehampton, was in fact far more subversive than she first appeared. And the truly amazing thing is that Osbert was able to show his work on the front page of Beaverbrook's, Daily Express, undermining everything that the Express stood for in a subtle and quite saucy way."

Charles Peattie, who draws the "Alex" cartoon in the Daily Telegraph, profited from attending the same school as Sir Osbert. "I was at Charterhouse, where Osbert Lancaster had been at school, and because of him and Max Beerbohm (another "Old Carthusian" cartoonist) there was a kind of tradition of cartooning which I think I benefited from," he says.

"I met him once at an exhibition of his cartoons there, which included other drawings by past students, including myself. He looked vividly like a character from his own cartoon universe, with a dandyish suit, big watery eyes and a flamboyant moustache. He was quite nice to me; told me I should draw bigger. I followed his advice."

He wasn't the only one to do so. Michael Heath, who draws for several British publications, including The Independent and The Spectator, says Sir Osbert's drawings were "unsurpassed" because of his "ability to accurately depict the minutia of historical details from any era... all while injecting immense humour into his work. No one could do that now".

Cartoons and Coronets: The Genius of Osbert Lancaster is at The Wallace Collection, London W1 from 2 October 2008. www.wallacecollection.org. A book of the same name by James Knox is published by Frances Lincoln Ltd on 2 October.