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    Jerry/"Daphne" 
Played By: Jack Lemmon

  • Attractive Bent-Gender: Osgood falls head over heels for Jerry in disguise as Daphne.
  • Becoming the Mask: He's genuinely thrilled at the prospect of marrying a millionaire...even if said millionaire is the same gender as he is.
  • Deadpan Snarker: 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.
  • Disguised in Drag: Hiding from the Mafia by pretending to be a female musician, as seen in the page image.
  • Gold Digger: He plans to marry Osgood and reveal his true identity immediately after in order to get alimony payments.
  • Heterosexual Life-Partners: With Joe. According to him, the two have been living together for three years, and Joe is rather insistent they do everything together.
  • Homoerotic Subtext: 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 Osgood is completely unfazed by Jerry's real gender). On a side note, Joe and Jerry are Heterosexual Life-Partners, 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.
  • Mad Libs Catchphrase: "What are you giving me with the [x]?"
  • Sobriquet Sex Switch: Averted. He rejects Joe's suggestion of going as Geraldine and chooses Daphne instead.
  • Starving Artist: Joe and Jerry are poor musicians who have to sell their coats to make ends meet.
  • Vitriolic Best Buds: He's none too happy going along with Joe's schemes, but remains on friendly terms nonetheless.

    Joe/"Josephine"/"Shell Oil Junior" 
Played By: Tony Curtis

  • Catchphrase: "You don't say."
  • Child Hater: He bullies a little kid on the beach in order to snag a spot from which to spy on Sugar.
  • Disguised in Drag: Hiding from the Mafia by pretending to be a female musician, as seen in the page image.
  • Jerk with a Heart of Gold: He genuinely feels bad for breaking Sugar's heart near the end. He even tells her that she deserves someone better than him.
  • Ladykiller in Love: He used to be a a sleaze who wasn't above lying, stealing, and taking money (among other things) from girls before ditching them. Originally, he just wanted to get Sugar into bed, but he ended up genuinely falling for her.
  • Meganekko: 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 Purely Aesthetic Glasses), though he behaves more like a Stoic Spectacles.
  • Mock Millionaire: Pretends to be the owner of Shell to attract Sugar (who earlier told "Josephine" that she wants to marry a millionaire).
  • Same Language Dub: Tony Curtis struggled keeping a falsetto as Josephine, requiring Paul Frees to dub some of his dialogue.
  • Skewed Priorities: 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.
  • Sobriquet Sex Switch: From Joe to "Josephine".
  • Starving Artist: Joe and Jerry are poor musicians who have to sell their coats to make ends meet.
  • Stoic Spectacles: He feigns disintrest in Sugar as "Junior" at first in order to make her more attracted to him.
  • Unsympathetic Comedy Protagonist: He comes across as a total sleazebag who is not above lying, theft and even cruelty to children just to get into Sugar's pants.
  • Wealthy Yacht Owner: 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 Disguised in Drag), so while he takes Daphne for a night on the town, Joe sneaks Sugar into Osborne's yacht and pretends it's his.
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    "Sugar Kane"/Sugar Kowalczyk 
Played By: Marilyn Monroe

  • All Girls Want Bad Boys: She's attracted to saxophonists who treat her like crap.
  • Can't Get Away with Nuthin': 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.
  • The Chanteuse: She is the lead singer of an all-female jazz band and we get to see some steaming hot performances at the hotel bar.
  • The Ditz: Sugar is... not bright.
  • Dumb Blonde: Beautiful blonde hair... ditzy disposition. She even shamelessly admits it to Joe/Josephine a few times. Being a Fool for Love and Alcohol-Induced Stupidity may also be factors.
  • Dumb Is Good: God bless her, Sugar is the sweetest person you could ever hope to meet, but she's rather lacking in the brains.
  • Gainaxing
    • The scene where Sugar climbs into bed to rub 'Daphne's' feet in a skimpy nightie. No bra.
    • Also, Sugar 'shakes' rather vigorously during and after 'Running Wild'.
  • Gold Digger: 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.

    Osgood Fielding III 
Played By: Joe E. Brown

  • Abhorrent Admirer: To "Daphne" at first, who was none too thrilled at the prospect of spending the evening with him, especially after the incident at the elevator.
  • Anything That Moves: He's had multiple marriages, won't take no for an answer from "Daphne", and doesn't even seem to mind that she's really a man.
  • Ambiguously Bi: 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 If It's You, It's Okay or if he actually is bisexual.
  • Catchphrase: "Zowie!"
  • Dirty Old Man: Jerry even names him as such at one point.
  • If It's You, It's Okay: "Well, nobody's perfect."
  • Momma's Boy: 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.
  • Obfuscating Stupidity: Osgood isn't quite as dumb as he acts.
  • Serial Spouse
    Osgood: I've been married seven or eight times.
    "Daphne": You're not sure?
    Osgood: Mama is keeping score.
  • Signature Laugh: Well, more an asthmatic wheeze than a laugh, but still...
  • Wealthy Yacht Owner: "Shell Oil" even borrows his so that he can appear to be this to Sugar.

    Spats Columbo 
Played By: George Raft

  • Big Bad: 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 as women. At least until he is killed by his boss, Little Bonaparte, who takes over as main villain for the last part of the film.
  • Catchphrase: "Big joke." Also his Famous Last Words.
  • Determinator: Nobody witnesses one of his hits and lives to tell about it - even if they escape to Florida dressed as women.

    Sweet Sue 
Played By: Joan Shawlee

  • Catchphrase: "BIENSTOCK!!!"
  • Control Freak: She runs a tight ship, forbidding her girls from drinking (justified, since Prohibition is still in effect) and fooling around with men.
  • Ironic Name: She doesn't have that sweet a disposition.
  • Spider-Sense: Her ulcer tells her there's something funny about "Josephine" and "Daphne".
  • Team Mom: She's the conductor and resident disciplinarian of the girls' jazz band.

    Beinstock 
Played By: Dave Barry

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