"How is a Woman Like a Watermelon" examines two of Richard Brautigan's novels, In Watermelon Sugar and An Unfortunate Woman, as they relate to each other in ways that offer a better understanding of each. This paper enriches an understanding of Brautigan's work by exploring the historical context of his writings, studying his style and presenting diverse interpretations in a mutually inclusive way that complements the multifaceted qualities of his writing. By studying Brautigan's novels in a comparative manner, the essential and distinctive principles that drive Brautigan's work—his manipulation of genre, use of memory and a complex first person narrator as an author persona—are better understood. Because of Brautigan's use of the first person, this study advocates an analytical psychological analysis aimed at discerning underlying emotion within apparent personal detachment, the use of projection as a defense mechanism, and the psychological associative value of words, images and memories. An inclusive and comparative study that foregrounds these psychological elements will ultimately allow for a more complete and subtle analysis of Brautigan's work. / Master of Arts