This paper examines the metatheatrical elements in Luigi Pirandello's Henry IV. First, I will survey the theory on metatheater with an emphasis on the play within the play, role playing within the role, and self-reference. Then, I will try to analyze Henry IV and trace its metatheatrical elements. What I want to highlight here is how Pirandello employs these devices to bring to light his philosophical idea on theater and life as well as life and form. After a close examination, I found that, by plotting the play within the play, Pirandello discloses the process of theater-making as well as the fictional theatricality. In the role-playing games, Henry role-plays as an actor, a madman, a director, and the spokesman for Pirandello. His multiple roles along with the busybodies' double identities also break the theatrical illusion and successfully create the effect of estrangement for the audience. In addition, Henry, as Pirandello's double, also clarifies Pirandello's humor theory on the closeness between theater and life and the antithesis between life and form. Hopefully, the audience may recognize the disguises and deceptions in life and learn the humor Pirandello possesses.