This dissertation expands the definition of contemporary prison writings in Arabic literature to include works, written by ex-political prisoners, that are experimental and/or do not directly reference the prison experience. By examining Ghassan al-Jaba‘i’s Banana Fingers (Asabi‘ al-Mawz) and other Arabic literary works produced as a result of political imprisonment after 1960s, this project demonstrates that contemporary Arabic prison writings employ experimental aspects that challenge conventional views of what prison is and what it means to be a prisoner. This project shows that Arabic prison writings do not necessarily need to be realistic. The imaginative and fantastical are equally important. Moreover, this project shows that contemporary Arabic prison writings can tell stories whose function is not to educate the audience or to call for political action against state oppression but rather to aesthetically entertain and even to alienate the audience by manipulating literary devices in a manner that is unconventional and experimental. Therefore, this project examines contemporary prison writings in Arabic literature as a chain of aesthetic interventions against conventional views of the nature and function of Arabic prison writings. This project also includes an English translation of al-Jaba‘i’s Banana Fingers. While working on this translation, I have regularly consulted with al-Jaba‘i. In this translation, I have not sought to paraphrase al-Jaba‘i’s short stories to make them more accessible and intelligible to the English-speaking reader. Instead, I have attempted to capture what al-Jaba‘i said, precisely how he said it. I have also aimed at recreating his use of experimental and subversive features, particularly his use of the alienation effect.