Some of the world’s most powerful stories concern a scenario whereby a single, often eccentric, lonely or misunderstood, individual is pinned against a society that is often too uncaring, rigid or self-interested to accommodate or acknowledge their unique spirit, character or life outlook. These fictional characters often find themselves at sea with numerous societal expectations, rules or people around them, striving for understanding and meaning, while also perhaps battling prejudice. The list below comprises novels, both contemporary and classic, about such characters who are all trying to understand how they fit into this thing called Life, and why their outlook or personality appears so different from that of others. The surprising conclusion from the list below is that many of these stories are semi-autobiographical, dictated by the authors’ own real-life experiences.

Pnin (1957) by Vladimir Nabokov

One eccentric émigré professor finds himself increasingly out of depth in his own classroom and his new country of residence – this is the premise of Vladimir Nabokov’s witty novella, which he wrote relying on his own experience of teaching Russian literature at Cornell University in the 1950s. In an episodic fashion, the story presents the character of Professor Timofey Pavlovich Pnin in various situations as he tries to navigate the academic life of one university in the United States – Waindell College (a fictitious establishment). Professor Pnin confronts a language barrier, culture clash, and painful memories from his past as he tries to make sense of the increasingly-confusing-to-him life around him. Pnin might not have achieved its mainstream popularity the way Nabokov’s novel Lolita (1957) had, but it is still as sharp-witted and as brilliantly told. Nabokov’s observational powers in fiction were second to one, and they are on full display here, in this bitter-sweet story about trying to fit into a new environment.

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