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Insomnia, while being defined and treated as a sleep disorder in the field of medical discourse, has attracted other kinds of interest, too. Philosophers and writers have been intrigued by insomnia since antiquity. From their perspectives, the capability of being sleepless not only distinguishes humankind from animals but testifies to human awareness in its ceaseless striving for wisdom and truth. Insomnia appears as vigilance, an exalted state of mind well suited for philosophic reflection, intense scrutiny of the world, and sudden inspiration. Yet these moments of sustained productivity are inextricably bound to insomnia’s “dark” side, the fact that sleeplessness tortures the body and exhausts the mind, haunts the weary wakeful and makes him meditate on insomnia. Thus sleeplessness turns into an obsession with the potential to transform thinking into endless introspection, self-absorbed melancholy, if not misanthropic sarcasm. This course will examine representations of insomnia in modern philosophy, literature and film. We will analyze to what extent interpretations of sleeplessness in the humanities differ from those in medical and scientific discourse. Particular emphasis will be placed on the relationship between insomnia, subjectivity, thinking, and writing. Authors and films to be considered will include among others Emanuel Lévinas, Emil Cioran, Franz Kafka, Samuel Beckett, Ernest Hemingway, F. Scott Fitzgerald, Djuna Barnes, Gabriel García Márquez and Insomnia (2002; Christopher Nolan).