The Night Thoreau Spent In Jail

Content Warning: The source text and this guide discuss enslavement and racism.

Henry, the play’s protagonist, is a fictionalization of Henry David Thoreau. The stage descriptions describe him as a “young man—with a knife-like humor, fierce conviction and devastating individuality” (4). Henry’s adherence to his principles is uncompromising, and he is willing to be jailed for his refusal to pay his poll tax. The characters who know him best describe him in paradoxical ways—as “the saddest happy man” and the “happiest sad man” (5), and as someone who simultaneously wants nothing and too much—and these direct characterizations help to flesh out this fictional representation of a complex, flawed man.

Henry believes that to enjoy true freedom, a person must cast off society’s shackles, reject materialism, and become self-reliant. Each person must “BE [their] OWN MAN,” as he tells his students (28). Rather than following convention and working long hours to afford material things, he believes people should be free to pursue their real interests. If people choose to live simply, they can spend most of their time at leisure rather than consumed by work. This work ethic explains Waldo’s claim that “[Henry] worked on Sundays, and took the rest of the week off” (5).