Geoffrey Tennant's history of breakdown while performing Hamlet may have been inspired by Daniel Day-Lewis who suffered a genuine nervous breakdown in 1989 and became convinced on stage that he was talking to the ghost of his own father, the poet Cecil Day-Lewis. He walked off in mid-performance.
The character of Jack Crew may have been inspired by Keanu Reeves. Like Reeves, Jack is portrayed as an action film star with dark, handsome good looks but a reputation for being wooden on-screen. In 1995 Reeves portrayed the title role of Hamlet in Canadian theater and won rave reviews.
The fictional town of New Burbage and its theater festival are presumably named after Richard Burbage, and actor-manager who was the star of many original Shakespeare plays and who spearheaded, in 1597, the construction of the original Globe theater in London.
Paul Gross plays Geoffrey Tennant, a stage actor best known (before his mental breakdown) for his performance as Hamlet. In an episode of Due South (1994) titled "A Hawk and a Handsaw", Gross' character Benton pretends to be insane, not unlike the character of Hamlet. The name of the episode comes from a line in Hamlet where he tells Rosencrantz and Guildenstern that he can "tell a hawk from a handsaw" - that he is sane.
Michael Polley (Frank) and Sarah Polley (Sophie) are real-life father and daughter. In 2012, 'Sarah Polley' directed a documentary called Stories We Tell in which she reveals that Michael Polley is not actually her biological father, but she still considers him to be her real father.
The trivia item below may give away important plot points.
Oliver's final instructions regarding what is to happen to his skull after his death are a reference to a story about Chicago actor and improv instructor Del Close, who requested that after his death, his skull was to be donated to the Goodman Theatre for use as Yorick in its subsequent productions of Hamlet. After his death, Close's executor did indeed donate a human skull to the Goodman, and she claimed that it was Close's; but several years later, she admitted to The New Yorker that although she tried to carry out Close's wishes, the morgue wouldn't allow her to remove Close's head, so (in the spirit of improvisation) she instead bought a skull from a medical supply house and passed it off as Close's.