How does Dekker construct humor through language and wordplay? What other literary and dramatic techniques does he use to bring the narrative to life?

How are loyalty and friendship depicted among the characters? What actions or choices reveal the strength or limits of these bonds?

How does the play handle themes of ambition and personal aspiration? In what ways are different characters undone or elevated by pursuing their goals?

Compare and contrast The Shoemaker’s Holiday with another play from one of Dekker’s contemporaries dealing with different classes in London, such as Ben Jonson’s Bartholomew Fair (1614). How are the plays different or similar in their treatment of class, disguise, and/or the blurring of social boundaries?

Various characters, such as Rose, Lacy, and Ralph, face different external barriers, such as gender roles and class distinctions. How does the play explore the similarities and differences between these barriers?

Examine how the play explores the fluid nature of identity. How do characters play with ideas of identity? What do their experiences suggest about how identity is constructed and experienced?

The play is set in the 15th century, yet was written toward the close of the 16th century. In what ways does the play contain historically accurate depictions of English life in the 1400s? In what ways does it serve as a vehicle for exploring the anxieties and norms of Dekker’s own times?

Choose a secondary character in the text, such as Sybil or the Earl of Lincoln. How is she/he depicted? What is his/her role and wider significance in the text?