My Dinner with André serves as a fascinating convergence of two artistic minds, each with distinct approaches and backgrounds in theater. André Gregory emerges as an avant-garde luminary, known for his daring and unconventional projects that often challenge traditional boundaries of performance art. In a striking example of his innovative spirit, Gregory collaborated with a group of non-dancers under the choreography of Twyla Tharp for a ballet performance at New York City’s Town Hall in 1979. This endeavor, executed with utmost seriousness, exemplifies his willingness to explore uncharted territories in the arts.

Gregory's reputation as an experimental theater director was solidified during his tenure with the Manhattan Project, a groundbreaking theater group that nurtured his early connection with Wallace Shawn. His acclaimed adaptation of Alice in Wonderland, which enjoyed a five-year run and secured an Obie Award, underscores his ability to blend the fantastical with the theatrical, reminiscent of Alice's own whimsical journey following her White Rabbit.

In stark contrast, Wallace Shawn's theatrical journey is marked by a more traditional and introspective approach. His work, beginning with Our Late Night in 1974, directed by Gregory and awarded an Obie, reflects a penchant for exploring the inner lives of his characters. In My Dinner with André, Shawn portrays characters who, much like himself, navigate intense inner worlds while grappling with external constraints that tether them to more predictable realities.

This motif of internal conflict and external stasis resonates throughout Shawn's body of work. His play Aunt Dan and Lemon introduces a reclusive young woman named Leonora, nicknamed "Lemon" by a domineering family friend, Aunt Dan. This relationship, characterized by a series of manipulative dialogues, continues to dominate Lemon's life even posthumously, illustrating how psychological influences can persistently shape individual destinies.

Shawn's later works, such as The Fever and The Designated Mourner, further delve into these themes, capturing the intricacies of personal and societal conflicts. Throughout his career, Shawn has remained dedicated to dissecting the complexities of human nature, crafting narratives that resonate with audiences through their exploration of both the mundane and the profound.