* AdaptationDisplacement: What, you've never heard of "The Idyll of Miss Sarah Brown" by Creator/DamonRunyon?
* AlternativeCharacterInterpretation: Did Nathan believe Sky's fib about losing the bet? Or did he realize Sky won, but then put together that he lied so as not to hurt Sarah's reputation? If the latter, that heavily implies he let Sarah know Sky lied to protect her on purpose, so the two could make up.
* SugarWiki/AwesomeMusic: One of Broadway's most popular scores? Yeah, you can bet there's a bit of this.
** "Sit Down, You're Rocking the Boat" is regarded as one of the greatest [[{{Showstopper}} Showstoppers]] of all time, for for very good reason. It's energy is absolutely infectious, its gospel sounds awesome, and seeing Nicely of all people save the day gives it an extra emotional oomph behind all the comedy.
** There's a reason why "Luck Be a Lady" became a standard after the show came out, but the musical's version has a driving sense of urgency, and the choreography, depending on the production, is often incredible.
** "I'll Know" features Sarah Brown's soaring soprano, plus Sky Masterson ribbing her before wooing her with talk of "chemistry".
* BigLippedAlligatorMoment: The performance of the song "Pet Me Poppa" in the film (the cat showgirls performance song). It could have easily been cut, adds nothing to the plot, and is very over-the-top. Worse, it replaces "A Bushel and a Peck", which was actually one of the best-known songs from the musical and could be said to better represent Adelaide's love for Nathan.
* EnsembleDarkhorse: Nicely-Nicely Johnson is a ''very'' beloved character due to his many funny moments and especially for singing "Sit Down, You're Rocking the Boat". With that one number, [[{{Showstopper}} Nicely can stop the show cold]].
* HoYay: Given they're always together and sing an entire song admonishing guys going doll crazy, there's a bit of this to Benny and Nicely's dynamic.
* MemeticMutation: Go into the Website/YouTube comments of the 90s revival's Tony performance, and you're sure to see an assortment of comments and jokes about Creator/JKSimmons' hilarious LargeHam expressions [[FunnyBackgroundEvent throughout the number]].
* OlderThanTheyThink: Nicely-Nicely (the character) previously appeared on film in the 1942 Creator/LucilleBall-Creator/HenryFonda movie, ''The Big Street''. The movie was based on a Damon Runyon story, "Little Pinks." In this movie, Nicely-Nicely is played by Eugene Pallette instead of Stubby Kaye - and he doesn't sing. Lucy's character does, though.
* QuestionableCasting:
** Music/FrankSinatra is an odd choice for Nathan Detroit. Both because [[PlayingAgainstType the smooth, romantic actor proves a noticeable contrast to Nathan's anxious, comical nature]], and because of the four leading roles, [[IronyAsSheIsCast they cast an incredibly talented singer as the main character who sings the least]]. Though they did write Sinatra the new song "Adelaide" and give him the already existing title number to make up for the latter point. As for the first point, composer Frank Loesser himself didn't care for [[WagTheDirector Sinatra abandoning his numbers' intended comedic style for his usual romantic crooning]].
** There's also Creator/MarlonBrando as Sky Masterson. While Brando makes perfect sense as the dreamy and flirtatious Sky in the talking scenes, [[VocalDissonance his famously distinctive voice]] has been called ill suited for Masterson's musical numbers. Indeed, Sinatra didn't care for Brando's casting at all, feeing he should've played Sky instead, [[HostilityOnTheSet which caused much friction between the two]].
* RetroactiveRecognition:
** Before he became a widely known, beloved, MediaNotes/AcademyAward winning character actor, Creator/JKSimmons appeared as [[https://digitalcollections.nypl.org/items/b31f5d33-7c4a-17da-e040-e00a18062482 Benny Southstreet]] in the acclaimed 90s Platform/{{Broadway}} revival.
** In the background of the same performance, eagle-eyed viewers will notice a young Victoria Clark, decades before her acclaimed performances and two Tony wins for ''The Light in the Piazza'' and ''Kimberly Akimbo''.
* SignatureSong: While the show is home to many popular tunes, "Sit Down, You're Rocking the Boat" and "Luck Be a Lady Tonight" are it's most beloved, and [[{{Showstopper}} can very easily stop the show]].
* UnintentionalPeriodPiece: Among other things, the fact that Sky and Sarah could easily fly to Havana on a day's notice became this when UsefulNotes/FidelCastro took over Cuba in 1959 and US-Cuba relations went south, leading to Cuba closing its borders for decades until 2016.
* ValuesDissonance:
** The emphasis on the romantic dynamic of "guys and dolls" above all else falls a bit into this since decades later, since exposure and discussion of different sexualities and gender identities have proven that there's more to romance than just those two sexes coming together. [[{{Downplayed}} This is a rather tame example though]] as it's not due to offensive content so much as just the general public either being unaware or not understanding these concepts at the time, and the romance present is still applicable to non-heterosexual couples.
** A more serious example would be Sky letting Sarah have multiple alcoholic drinks without her knowing what's in it. Thankfully Sky never once tries anything untoward while she's drunk, but given the #METOO movement and the awareness of intoxicating girls to take advantage of them now, you can bet that piece wouldn't be included if the show were written nowadays.
** The ICanChangeMyBeloved trope exemplified by "Marry the Man Today" is seen by many as a flawed ideology that traps many people, particularly women, in toxic relationships. While it seems to work out for Sarah and Adelaide in this case, some productions cut the number for this reason.
** Gambling is taken both more and less seriously today compared to within the time period of the show. While many forms of gambling have become legalized and more socially acceptable overall, there is also a better understanding of compulsive gambling as an addictive behavior, not necessarily a moral failing.
* TheWoobie: Adelaide gets sick because she's so stressed out, and has ''three'' songs about how unhappy she is.
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