Pierre

Published in 1852 as the bewildering follow-up to the then-failed Moby-Dick, Pierre; or, The Ambiguities is Herman Melville's dark doppelgänger. On the surface, young Pierre Glendinning is the golden heir to a proud patrician family, betrothed to the blonde Lucy Tartan. But when a mysterious, dark-haired woman named Isabel claims to be his father's illegitimate half-sister, Pierre commits an act of catastrophic virtue.
To preserve his father's honor, he fakes a marriage to Isabel, is cast out by his mother, and descends into a Bohemian underworld of penniless writers and mad philosophers. Here, Melville abandons the high seas for the nightmare of the human mind. Stripped of wealth and sanity, Pierre attempts to write a book of truths in a world that demands lies. A revolutionary foray into modernist psychology, this is not the Melville of whaling adventures.
This is a corrosive satire of sentimental Gothic novels, a vicious assault on the American publishing industry, and a harrowing study of the soul destroyed by absolute ideals. Nearly two centuries later, Pierre remains the kraken of American literature: a beautiful, baffling, and brilliant catastrophe.