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[[foldercontrol]]

[[folder:Jerry/"Daphne"]]
->'''Played By:''' Creator/JackLemmon

* AmbiguouslyBi: When disguised as "Daphne", he seems to have developed genuine feelings towards Osgood. He also shows attraction to Sugar and the other girls on the train.
* AttractiveBentGender: Osgood falls head over heels for Jerry in disguise as Daphne.
* BecomingTheMask: He's genuinely thrilled at the prospect of marrying a millionaire... even if said millionaire is the same gender as he is.
%%* ButtMonkey
* DeadpanSnarker: Apparently the only way to stay sane when dealing with Joe (and Osgood) is to throw around snark.
-->'''Osgood:''' I'm Osgood Fielding the third.
-->'''Jerry/Daphne:''' I'm Cinderella the second.
* DisguisedInDrag: Hiding from the Mafia by pretending to be a female musician, as seen in the page image.
* GoldDigger: He plans to marry Osgood and reveal his true identity immediately after in order to get alimony payments.
%%* TheHero
* HeterosexualLifePartners: With Joe. According to him, the two have been living together for three years, and Joe is rather insistent they do everything together.
* HomoeroticSubtext: At one point Jerry-as-Daphne seems to be developing genuine romantic feelings for Osgood, much to Joe's consternation (and we later find out that [[spoiler: Osgood is completely unfazed by Jerry's real gender]]). On a side note, Joe and Jerry are HeterosexualLifePartners, Joe is very insistent that they do everything together and that what's Jerry's is his and while Jerry vocally objects, he goes along with it anyway.
** Though the last case may be more akin to them being like brothers, with Jerry being the little brother who gets bullied into doing things he doesn't want to.
* MadLibsCatchphrase: "What are you giving me with the [x]?"
* SobriquetSexSwitch: Averted. He rejects Joe's suggestion of going as Geraldine and chooses Daphne instead.
* StarvingArtist: Joe and Jerry are poor musicians who have to sell their coats to make ends meet.
* VitriolicBestBuds: He's none too happy going along with Joe's schemes, but remains on friendly terms nonetheless.
[[/folder]]

[[folder:Joe/"Josephine"/"Shell Oil Junior"]]
->'''Played By:''' Creator/TonyCurtis
* BespectacledCutie: Sugar believes that men who wear glasses are more gentle and vulnerable. Joe takes full advantage of this by dressing up as a bespectacled millionaire (wearing PurelyAestheticGlasses), though he behaves more like a StoicSpectacles.
* CatchPhrase: "You don't say."
* ChildHater: He bullies a little kid on the beach in order to snag a spot from which to spy on Sugar.
* DisguisedInDrag: Hiding from the Mafia by pretending to be a female musician, as seen in the page image.
* HeelRealization: When he falls in love with Sugar, he realizes how sleazy he's been with other women and tries to make things right with her.
* ImpliedDeathThreat: He warns "Daphne" not to blow his cover by saying "I heard a very sad story about a girl who went to Bryn Mawr. She squealed on her roommate...and they found her strangled with her own brassiere."
* JerkWithAHeartOfGold: He genuinely feels bad for breaking Sugar's heart near the end. He even tells her that she deserves someone better than him.
* LadykillerInLove: He used to be a a sleaze who would use girls for cars, money, and sex before ditching them. Originally, he just wanted to get Sugar into bed, but he ended up genuinely falling for her.
%%* TheLancer
* MockMillionaire: Pretends to be the owner of Shell to attract Sugar (who earlier told "Josephine" that she wants to marry a millionaire).
* SameLanguageDub: Tony Curtis struggled keeping a falsetto as Josephine, requiring Creator/PaulFrees to dub some of his dialogue.
* SkewedPriorities: When the Mafia shows up at the hotel, he's more interested in saying goodbye to Sugar (and giving her their only source of money, a diamond bracelet, as a going-away present) than in getting the hell out of Dodge before they get murdered.
* SobriquetSexSwitch: From Joe to "Josephine".
* StarvingArtist: Joe and Jerry are poor musicians who have to sell their coats to make ends meet.
* StoicSpectacles: He feigns disintrest in Sugar as "Junior" at first [[ReversePsychology in order to make her more attracted to him]].
* TookALevelInKindness: At the start of the movie, he's known for lying to and stealing from girls before ditching them. By the end, he's willing to give Sugar a diamond bracelet as an apology gift.
* UnsympatheticComedyProtagonist: He comes across as a total sleezebag who is not above lying, theft and even cruelty to children just to get into Sugar's pants. He even purposely trips Sugar on the beach in order to arrange a MeetCute with her.
* WealthyYachtOwner: Joe seduces Sugar Kane by pretending to be a millionaire with a yacht anchored offshore. Fortunately Osgood, a real millionaire, is in love with Daphne (really Jerry DisguisedInDrag), so while he takes Daphne for a night on the town, Joe sneaks Sugar into Osborne's yacht and pretends it's his.
%%* WholesomeCrossdresser
[[/folder]]

[[folder:"Sugar Kane"/Sugar Kowalczyk]]
->'''Played By:''' Creator/MarilynMonroe

* AllGirlsWantBadBoys: She's attracted to saxophonists who treat her like crap.
* AmbiguouslyBi: There's quite a bit of subtext implying she's attracted to "Josephine". Whether this means she's subconsciously picking up on the fact that "she" is actually a man in drag or has sapphic inclinations is unclear.
* CantGetAwayWithNuthin: She claims that everyone in the band drinks, but she gets in trouble for it most often. When a flask falls out of her dress at the end of the "Runnin' Wild" number, it takes a fib from "Daphne" to keep her from getting kicked off the train.
* TheChanteuse: She is the lead singer of an all-female jazz band and we get to see some steaming hot performances at the hotel bar.
* TheDitz: Sugar is... not bright.
* DumbBlonde: Beautiful blonde hair... ditzy disposition. She even shamelessly admits it to Joe/Josephine a few times. Being a FoolForLove and AlcoholInducedStupidity may also be factors.
* DumbIsGood: God bless her, Sugar is the sweetest person you could ever hope to meet, but she's rather lacking in the brains.
* EasilyForgiven: When Joe reveals at the end that he's yet another saxophone playing jerk and an especially deceitful one to boot, she's still as in love with him as ever.
* GoldDigger: Played with. She wants to marry a millionaire because she's sick of being used by sleazy men and doesn't want to be mooched off of again, rather than out of greed.
%%* HeadTurningBeauty
* HomoeroticSubtext: Sugar doesn't seem to initially mind getting a full-on kiss from [[spoiler: Josephine]].
* ImpossiblyLowNeckline: Sugar's stage dresses. There's some transparent material holding it up to keep her from being NippleAndDimed, but the opaque material only covers a minimal amount.
* MsFanservice: It's Creator/MarilynMonroe, the original Sex Goddess, at her finest.
* NationalStereotypes: She's Polish (well, Polish-American) and rather dim.
* ObfuscatingStupidity: Sugar isn't ''quite'' as dumb as she acts.
* {{Sexophone}}: Sugar has a thing for sax players.
* SexyBacklessOutfit: Sugar's gown for "I Wanna Be Loved By You".
* StageName: It's a PunnyName, but at least it doesn't sound too Polish.
* SupermodelStrut: She's first introducing strutting past Jerry and Joe, who both get distracted by the sway of her hips.
-->'''Jerry:''' Look how she moves. That's just like Jell-O on springs. She must have some sort of built-in motors.
[[/folder]]

[[folder:Osgood Fielding III]]
->'''Played By:''' Joe E. Brown

* AbhorrentAdmirer: Pursues Jerry as "Daphne" through the whole film and the only really attractive part of him is the fact he's rich (looks like a toad, MamasBoy, etc). The final gag is Jerry desperately tossing a HurricaneOfExcuses to get Osgood off his back after he says he wants to marry "Daphne", only for Osgood to nonchalantly disregard all of them (even the fact Jerry is a man).
* AmbiguouslyBi: Is unfazed when "Daphne" reveals to have been a man named Jerry all along, famously delivering the final line "well no one is perfect", implying that he doesn't even care if he falls in love with a man. Although due to the time the film was released it's kind of unclear if it's a case of IfItsYouItsOkay or if he actually is bisexual.
* CatchPhrase: "Zowie!"
* DirtyOldMan: Jerry even names him as such at one point.
* IfItsYouItsOkay: He's not at all fazed by the revelation that his fiancée is a man, saying: "Well, nobody's perfect."
%%* LargeHam
%%* ManChild
* MommasBoy: Osgood's mother gets the last word in who her son's allowed to marry. Considering his age, it's a wonder she's even still alive.
* ObfuscatingStupidity: Osgood isn't ''quite'' as dumb as he acts.
* SerialSpouse
-->'''Osgood:''' I've been married seven or eight times.
-->'''"Daphne":''' You're not sure?
-->'''Osgood:''' Mama is keeping score.
* SignatureLaugh: Well, more an asthmatic wheeze than a laugh, but still...
* WealthyYachtOwner: "Shell Oil" even borrows his so that he can appear to be this to Sugar.
[[/folder]]

[[folder:Spats Columbo]]
->'''Played By:''' George Raft

* BigBad: He is the Chicago mafia boss responsible for gunning down a rival gang and hunting down Joe and Jerry as witnesses, forcing them to go undercover [[DisguisedInDrag as women]]. [[spoiler:[[DiscOneFinalBoss At least until]] he is killed by [[TheManBehindTheMan his boss]], Little Bonaparte, who takes over as main villain for the last part of the film.]]
* CatchPhrase: "Big joke."
* {{Determinator}}: Played with. Sure, nobody witnesses one of his hits and lives to tell about it, even if they escape to Florida dressed as women -- but he's in town on unrelated business, and ran into Joe and Jerry through pure happenstance and bad luck.
* DragonWithAnAgenda: He plans to KillAndReplace Little Bonaparte as Mafia crime lord before being sidetracked by chasing Joe and Jerry.
%%* FauxAffablyEvil
* {{Leitmotif}}: His appearance is always accompanied by a menacing violin/kettle drum score.
* NoHistoricalFiguresWereHarmed: As a prohibition-era Chicago mafia boss who has rival gangsters whacked in a scene reminiscent of the [[https://en.wikipedia.org/wiki/Saint_Valentine%27s_Day_Massacre Saint Valentine's Day Massacre]], he obviously takes some cues from Al Capone.
* VileVillainSaccharineShow: Things get ''far'' more serious when he's in the picture.
* VillainousFashionSense: His nickname comes from the fact that he wears spats ''all'' the time. He even uses it as an alibi, albeit not a remotely convincing one.
-->'''Mulligan:''' D'ja ever hear of the [=DeLuxe=] French Cleaners on Wabash Avenue?\\
'''Spats:''' Why?\\
'''Mulligan:''' Because the day after the shootin' you sent in a pair of spats. They had blood on 'em.\\
'''Spats:''' [[CutHimselfShaving I cut myself while shaving]].\\
'''Mulligan:''' You shave with spats on?\\
'''Spats:''' ''[defiant]'' I ''sleep'' with my spats on.
[[/folder]]

[[folder:Sweet Sue]]
->'''Played By:''' Joan Shawlee

* CatchPhrase: "BIENSTOCK!!!"
* ControlFreak: She runs a tight ship, forbidding her girls from drinking (justified, since Prohibition is still in effect) and fooling around with men.
%%* DeadpanSnarker
* IronicName: She doesn't have that sweet a disposition.
%%* NoIndoorVoice
* SpiderSense: Her ulcer tells her there's something funny about "Josephine" and "Daphne".
* TeamMom: She's the conductor and resident disciplinarian of the girls' jazz band.
[[/folder]]

[[folder:Beinstock]]
->'''Played By:''' Dave Barry

* BeleagueredAssistant: To Sweet Sue.
* SmallRoleBigImpact: Joe "borrows" his sailor's clothes for his "Shell Oil" persona.
[[/folder]]