Virginia Woolf: Mrs Dalloway (1925)
Doris Lessing: The Golden Notebook (1962)
Simone de Beauvoir: The Mandarins (1954)
Ken Kesey: One Flew Over the Cuckoo's Nest (1962)
Sylvia Plath: The Bell Jar (1963)

Madness - that derangement of mind, emotions, senses - has long been of interest to novelists, but never so much so as with the rise and rise of the mind-doctoring professions in the 20th century. By saying that he had learned much of what he knew from novels - only then to label writers "neurotic" and setting out to provide his own understanding of the inner life - Freud threw down the gauntlet. Writers have been responding, either by using his ideas for their own purposes, or by rejecting the straitjacket of the mind doctors and their often narrow notions of sanity ever since.

The romantic side of madness - derangement as a journey into inner heights and depths that mirror society's ills and function as a greater, if disruptive, sanity - figures in Virginia Woolf's Mrs Dalloway and Doris Lessing's The Golden Notebook. Septimus, Woolf's damaged hero and her own stand-in, is exasperated by his smug psychiatrist who worships the goddess Proportion. So, too, is Lessing's Anna Wulf by her analyst, Mother Sugar, whose sweet palliatives can do nothing to dislodge Anna's writer's block. Only the descent into madness will achieve that.

In The Mandarins, her great novel of the post second world war years, Simone de Beauvoir makes her heroine, Anne, an analyst, but one who has grown weary of her own profession's tendency to lock individuals into the straitjacket of a "case". Only the madness of love will rupture the depressive case she has become.

Meanwhile, Vladimir Nabokov, who named Freud "the Viennese witch doctor", created in Humbert Humbert a superlative saboteur of shrinks. Lolita is, among much else, a stunning parody of a psychiatric case study, presented to us by Dr John Ray, who names Humbert as a pervert and warns that psychopathology threatens the world to the same extent that communism does.

Psychiatrists also feature as clinical McCarthyites in that extraordinary indictment of mid-century asylum life, One Flew Over the Cuckoo's Nest, where the mad and the sane are indistinguishable but for their labels. Until recent novels by Hanif Kureishi among others put an end to the tug of war between writers and shrinks, Sylvia Plath's The Bell Jar was one of the few fictions to present their influence as benign. In Plath's novel, the analyst is seen as a good mother who can shepherd her disturbed adolescent heroine into womanhood.

• Lisa Appignanesi's latest book is Mad, Bad and Sad: A History of Women and the Mind Doctors from 1800