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1* AwardSnub: While the show did quite well at the Tonys, it lost Best Musical to ''Theatre/JerseyBoys''. It's otherwise strong performance can either be seen as making this snub more bearable or worse.
2* TheBardOnBoard: Many actors and directors have noticed a connection between ''Drowsy'' and Shakespeare's ''Theatre/AsYouLikeIt'': Four weddings, main couple falls in and out of love, girl pretends to be something she isn't, last marriage comes out of nowhere, priest for the wedding comes down from the sky...
3* BigLippedAlligatorMoment: The Man puts in the wrong record, and we get to hear "Message From a Nightingale", which has absolutely nothing to do with the plot.
4* CultClassic: Not the most mainstream show, but it's a favorite of many for it's expert pastiching of old school shows that both lets you laugh at them and love them.
5* SugarWiki/FunnyMoments: The opening monologue, the spit-take scene, "Bride's Lament", literally ''every scene'' in which the Chaperone or Aldolpho appear, 95% of Man In Chair's comments, the record skipping at the end of "Toledo Surprise", the gangsters' puns, "Message From A Nightingale"...it's a cliche to end entries like this with "let's just say the whole show", but ''The Drowsy Chaperone'' has '''earned it.'''
6* SugarWiki/HeartwarmingMoments: "[[https://www.youtube.com/watch?v=t4_qkZTxjhA Finale Ultimo]]," in which the Man in Chair imagines being surrounded by his favorite characters and joining in their final song. It's...just hard to listen to it without feeling happy.
7* NarmCharm: Despite being extremely silly, the lyrics for Bride's Lament are still quite touching.
8* TheWoobie: Man In Chair, especially once you learn his backstory, where he's been quite unlucky in love and now lives alone. Though it's played for laughs for most of the show, but the final monologue with "Finale Ultimo" really solidifies it by showcasing how pathetic he is, relying on old musical records to keep his spirits up.

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