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Nightwood, by Djuna Barnes is a landmark piece of modernist literature, and is a personal favourite of Derek Quinlans. The book is one of the earliest examples of gay literature. It's also very notable for its intense, gothic prose style. It uses many modernist techniques and some people have even called it metafiction. It has a typically fragmented narrative and a very unusual form that recalls Joycean techniques.
The manuscript was said to be finished as early as 1932 but it took Barnes several years to find a publisher. It was eventually published in 1936. The story follows Robin Vote and also Nora Flood, who eventually move to Paris together to seek security in their relationship. It also features the character of Dr Matthew O'Connor, a transsexual who pretends to be a doctor and performs deliveries and abortions in a futile struggle for legitimacy.