* SugarWiki/AwesomeMusic: Each season has a new theme song corresponding to the play they're putting on that season, but it's hard to top Season 1's opener, [[https://www.youtube.com/watch?v=LMYD2CfJM2o Cheer Up, Hamlet]].
* GeniusBonus:
** If you've ever been involved in theater, you will understand a good deal more of the show. If you ''also'' have a thorough knowledge of Shakespeare, it takes on new depths.
** Jack translating Hamlet's lines into colloquial modern day English comes off at first like just more of the Hollywood action star being hopelessly out of his depth. But if you think about it a little more, and in light of how he's ultimately able to do the role justice, it shows that he actually does understand what the lines mean rather than just parroting famous quotes, which any good Shakespeare actor will tell you is a must.
* HilariousInHindsight:
** Oliver's will asks that his skull be used in productions of ''Theatre/{{Hamlet}}'', much to the other character's disgust. In 2008, [[http://news.bbc.co.uk/2/hi/entertainment/arts_and_culture/7749962.stm the skull of pianist Andre Tchaikowsky was used for exactly that purpose]], fulfilling a request in his will.
** The final season of the show focused on a staging of ''Theatre/KingLear''; Creator/PaulGross, who played Geoffery in this series, went on to play the title role in the 2023 season of the Stratford Festival.
* {{Squick}}: After his death, Oliver's will states that he wants his head removed from his body, boiled, and the skull used in all future productions of ''Theatre/{{Hamlet}}''. Even the other characters are grossed out.
* TearJerker: Charles Kingman's ''Theatre/KingLear'', made even more poignant by the fact it was William Hutt's last performance before he died of leukemia.
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