** It's very easy to add different interpretations to The Leading Player, especially if they're played by different genders. For example, some versions with a female Leading Player portray her as [[TheVamp a vamp]] and as a [[BettyAndVeronica Veronica to Catherine's Betty]].
** There is at least one production with a male Leading Player whose interactions with Catherine make it clear that that the two are in [[DomesticAbuse a possibly abusive relationship]]. This makes his anger with Catherine's part much creepier and her adoration of Pippin's kindness much more desperate and sad.
* Louisís sexuality: In the PlayWithinAPlay, his character seems to have been written as gay. But the IncestSubtext could be [[CastIncest unintentional]] for the InUniverse play. There could be a RomanceOnTheSet between the players portraying Louis and Fastrada, not helped by the fact that Fastrada is PlayingGertrude.
* CrowningMusicOfAwesome: "Corner of the Sky" and "Magic To Do", full stop.
* EarWorm: "MAGIC TO DO".
** "Oh, it's time to start livin'! Time to take a little from this world we're given!"
* EvilIsSexy: Fastrada, obviously. But to a lesser extent, Leading Player. Whether played by a man or woman his/her choreography is usually quite sexual, not surprising since this show was originally directed and choreographed by Creator/BobFosse.
* FamilyUnfriendlyAesop: [[spoiler: Searching for fulfillment and satisfaction in life will only lead to self-destruction, and a normal boring life, while happy, will always leave you feeling trapped and unfulfilled. So don't wish for freedom, kids. Also a normal life will never have magic in it.]]
* [[FunnyAneurysmMoment Funny Aneurysm Line]]: "'When you're as old as I, my dear, ''and I hope you never are...''"
** "We've got parts to perform, ''hearts to '''warm'''...''
* HilariousInHindsight: The lyric "Sages tweet that age is sweet" from "No Time At All" has a new context with the advent of Twitter. This might also count as HaveAGayOldTime.
** "Glory" is a juxtaposition of catchy music and surreal gore that can be extremely unsettling when handled skillfully.
** The 1981 TV version of "With You" shows Pippin getting increasingly in over his head as his new "friends" push him towards voyeurism, drugs, sadomasochism, and random hookups, and by the time he realizes that they're using him, they've discarded any pretense of caring about his safety.
** When Catherine starts to break character: "He touched my face--''the others never did that.''" [[FridgeHorror Wait, others?]] [[spoiler:Just how many "Pippins" have been led to their doom?]]
** Berthe is in one scene and has one song. And yet her song is among the most famous in the musical, and she often gets the most applause at curtain calls.
** Andrea Martin's turn as Berthe in the revival was so great that they gave her a line in "Magic To Do"... specifically "Humor, handled by a master". This was, in fact, going back to the original published edition following the Fosse production, but it was rarely enforced in actual practice.
* SpaceWhaleAesop: [[spoiler: Don't listen to those voices in your head encouraging you to seek fame and glory because they really just want you to set yourself on fire.]]
* SurpriseCreepy: Depending on what you think of the earlier parts of the show, [[spoiler:the Lead Player's behavior towards Catherine when she first appears and the entire Finale]] may be shocking and unsettling.