These are my nominations.
1. Pnin by Vladimir Nabokov
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Goodreads: One of the best-loved of Nabokov’s novels, Pnin features his funniest and most heart-rending character. Professor Timofey Pnin is a haplessly disoriented Russian émigré precariously employed on an American college campus in the 1950s. Pnin struggles to maintain his dignity through a series of comic and sad misunderstandings, all the while falling victim both to subtle academic conspiracies and to the manipulations of a deliberately unreliable narrator.
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2. De Profundis by Oscar Wilde
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Goodreads: De Profundis (Latin: "from the depths") is a 50,000 word letter written by Oscar Wilde during his imprisonment in Reading Gaol, to Lord Alfred Douglas, his lover. Wilde wrote the letter between January and March 1897; he was not allowed to send it, but took it with him upon release. In it he repudiates Lord Alfred for what Wilde finally sees as his arrogance and vanity; he had not forgotten Douglas's remark, when he was ill, "When you are not on your pedestal you are not interesting." He also felt redemption and fulfillment in his ordeal, realizing that his hardship had filled the soul with the fruit of experience, however bitter it tasted at the time.
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3. Historia Calamitatum by Peter Abelard
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Wikipedia: This extensive letter provides an honest self-analysis of Peter Abelard's up to the age of about fifty-four. The Historia Calamitatum provides readers with knowledge of his views of women, learning, monastic life, Church and State combined, and the social milieu of the time. Within this important piece of literature, not only is one side of one of history's best-known love stories told, but integral parts of the history of the Middle Ages are revealed. It should be particularly noted that this book was written at a time when Western Europe was just surfacing into the world of philosophy. The Historia is exceptionally readable, and presents a remarkably honest self-portrait of a man who could be arrogant and often felt persecuted. It provides a clear and fascinating picture of intellectual life in Paris before the formalization of the University, of the intellectual excitement of the period, of monastic life, and of his affair with Heloise, one of history's most famous love stories. Throughout this letter, Abelard emphasizes how persecuted he feels by his peers. He quotes saints, apostles, and at one point, compares his struggles in likeness to those of Christ.
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