Spalding Gray’s works are deeply autobiographical. He used both his own name and the names of those with whom he interacted in his monologues. When he performed, he did so behind a desk with a microphone, notepad, and glass of water as his only props. He made no attempt to disguise his identity the way an actor playing a role typically would. It was this transparency that raised the most basic question about Gray’s work: Was he just Spalding Gray, or was he an actor playing the role of Spalding Gray? Moreover, because he made an effort in his daily life to observe and remember every bit of minutia that happened to him as fodder for his next monologue, did he, as an actor, ever stop performing Spalding Gray?

Gray’s character is fairly easy to describe. Much like Woody Allen’s persona of the nebbishy New York Jew, Gray plays the nebbishy, New England WASP (white, Anglo-Saxon Protestant) actor and docile male. It is this emasculated, paranoid persona of Spalding Gray that Gray took on in all of his monologues. It also become the persona that he took on in real life.

This is not to say that Gray did not take on a variety of characters in performing his pieces. To the contrary, he often assumed the voice and subtle body movements of the characters with whom Spalding Gray interacted. It was these changes in character that further call into question whether Gray was being himself or performing a role. Unlike impressionists who rarely interact as “themselves” with their impressions, Gray freely conversed with himself as someone else. Without differentiating between how he played others and how he played himself, Gray further blurred the lines that separate reality from history and from performance.

Many of Gray’s monologues reference his search for a “perfect moment.” This longing for the perfection that he sought in his life propelled many of his stories. This moment however, is almost always difficult to achieve and, as the name “perfect moment,” suggests, only lasts briefly. It is this search for perfection, no matter how brief, that drove Gray to action. The moments, when related to the audience, are almost always anticlimactic to the quest to achieve them.

Gray’s work is often referred to as “sit-down” comedy, as if the only difference between his work and the storytelling of a standup comedian such as Bill Cosby is his or her presentation to the audience. There are three major distinctions that should be made between the two art forms. First, Gray’s work was intimate, at times uncomfortably so. He spoke freely about his sexual anxieties, conquests, and misadventures; his philandering; his mother’s suicide; his paranoia; and a host of other issues that would seem to be off-limits, or at least unsavory, for a comic with the goal to simply entertain. Gray’s work, by his own admission, was a type of talk therapy for him to work out his personal demons in front of an audience. By extension, he hoped that his audience would relate to his misadventures and experience a similar catharsis. Second, Gray used his very personal stories to discuss greater issues that affect society. He expected that his very small story would shed light on larger issues affecting others. Third, Gray’s audience expected performance art, not standup. This may be the most significant difference between Gray and standup comedians. Expectations affected the way the audience interacted with him. These expectations also added gravity to his pieces that they may or may not have deserved.

Gray’s texts, as they exist in published form, are typically transcriptions of...