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Susan (Katharine Hepburn), Bringing Up Baby (1938)
Katharine Hepburn's Susan in Bringing Up Baby is sort of a proto-hot mess, but she certainly is a mess. For starters, she's the type of woman who thinks it's okay to keep a leopard around. She also displays classic hot mess behavior, like ripping her dress in a public setting.
Hot Mess Qualities: Poor grasp of reality, flirting with danger (a.k.a. leopards)
Sugar (Marilyn Monroe), Some Like It Hot (1959)
Marilyn Monroe is at her most sultry in the classic Some Like It Hot, but her Sugar has hallmarks of a hot mess. She joins an all-girl band so she doesn't fall in with so many sax players. She sneaks booze. She's hilarious, but there's also an underlying sadness to her.
Hot Mess Qualities: Likes a good drink a little too much, has a thing for sax players
Mary (Parker Posey), Party Girl (1995)
In Party Girl's opening scenes, Mary gets arrested for a variety of offenses, including "illegal operations of a social club" and "possessions of controlled substances." As the title indicates, she's a bit of a wild child. But she gets her life in order by learning the Dewey Decimal System when she starts working at her godmother's library branch.
Hot Mess Qualities: Predilection for, um, partying; financial instability
Gracie (Sandra Bullock), Miss Congeniality (2000)
Sure, Gracie is a super competent FBI agent, but she doesn't exactly scream grace and poise. (Even though, as played by Sandra Bullock, she's gorgeous.) She's inherently disheveled, which makes things awkward when she has to go undercover as a beauty queen.
Hot Mess Qualities: Sloppiness, clumsiness
Bridget (Renée Zellweger), Bridget Jones' Diary (2001)
Ah, Bridget, you wanton sex goddess. When we first meet Bridget, she's trying to reform her ways: She wants to lose weight, remember to put her panties in the laundry, and date a "nice sensible boyfriend." But Bridget's hot messiness is too ingrained in her personality to be fully eradicated. It's in there so deep that there's a third movie coming out this year, in which she's in a very hot mess predicament: She does not know who the father of her baby is.
Hot Mess Qualities: Prone to smoking, drinking, falling for bad men