Although the two stories never directly connect, their situations often playfully overlap, so that both Williams must endure similar experiences and make related decisions. For example, Willie Greenberg goes on an eventful journey to deliver an oversized psychedelic contraband mushroom, while the Bard is tasked with delivering a mysterious locked box containing a religious relic. Both journeys are inherently dangerous with the final outcome uncertain. Their plights also interconnect in humorous ways regarding the women in their lives.

In his first novel, Winfield presents two likeable, interesting Williams, with the 1582 version of Shakespeare being "a combination of fact, legend, and surmise." The many allusions to Shakespearean text (throughout chapters on both Williams) provide challenges for scholars and fans of the Bard to find the origin of each quotation. As in the works of Shakespeare, the book contains numerous sexual references, some subtle and some less so. While the style and story are engaging throughout, My Name is Will is indeed (as the subtitle indicates) a novel about casual sex, hallucinogenic drugs, and all things Shakespeare - subjects that will attract some readers as strongly as they will repel others.