by Nathaniel R
Mikey Madison, Best Actress winner for "ANORA"With Mikey Madison's much buzzed about semi-surprising Best Actress win for Anora (2024) and Madison and her writer/director Sean Baker both paying tribute to sex workers in their speeches, let's talk sexworkers and the Oscars. It is a myth that playing a sex worker will get you an Oscar but it is also not wholly false that these roles are of great interest to Hollywood. Many actresses have been celebrated for playing women of ill repute whether they're traditional prostitutes, strippers, sex therapists, or it happens to be a character detail that they used to trade sex for money, or whatnot. What this says about Hollywood and the public's taste in entertainment is... well, it says many things... but they do call it 'the oldest profession' for a reason.
Male actors are not nominated for this sort of role (which also says a lot about society and Hollywood) even when they deserve to be...
Just a few examples in my lifetime of movie and Oscar watching include snubbed greatness like River Phoenix's best performance in My Own Private Idaho (1991), Jude Law's stylized genre work as "Gigolo joe" in A.I. (2001), and Matthew McConaughey's single best performance as stripper/entrepeneur "Dallas" in Magic Mike (2012) which would have made an infinitely more deserving Oscar win for him than Dallas Buyer's Club (2013) the following year.
In fact the only examples I could think of were vague and/or sex-work adjacent, like William Holden in Sunset Blvd (1950) who is a reluctant gigolo or 'kept boy' of sorts and Morgan Freeman who plays a pimp brilliantly in Street Smart (1987), and the odd hustling duo of Dustin Hoffman and Jon Voight in Midnight Cowboy (1969) with Voight the only man nominated who inarguably fits the bill of being nominated for playing a prostitute.
Since the list of every female nomination for a sex worker character would too long, we've limited it to WINNERS ONLY. Turns out there are 14-17 (depending on what you think counts) across Best Actress and Best Supporting Actress in the 97 years of Oscar competitions.
The definition of prostitution here is loose (no pun intended) as you'll see. Let me know if I missed anyone as sometimes the oldest profession is a small character detail.
ALL THE WOMEN WHO HAVE WON OSCARS
BY PLAYING SEX WORKERS (OR CLOSE ENOUGH...)
Janet Gaynor in the silent Seventh Heaven
1st Academy Awards
Best Actress Janet Gaynor in Street Angel AND Seventh Heaven (1928).
While the very first Best Actress winner actually won one statue for three roles simultaneously (before they had ironed out the current rules), two of the three characters were prostitutes. Isn't it both telling and gallows humor amusing that the very first Best Actress win was an unmistakable Virgin/Whore statement; in the third and most famous film within her winning silent trio, Sunrise: A Song of Two Humans, Gaynor plays a saintly woman simply known as "The Wife".
5th Academy Awards
Best Actress Helen Hayes in The Sin of Madelon Claudet (1931)
Women falling into prostitution through poverty / desperation is an endless trope in dramatic fiction.
The Razor's Edge
19th Academy Awards
Best Supporting Actress Anne Baxter in The Razor's Edge (1946)
Arguable classification. While this character is remembered more as an alcoholic (an even more common Oscar-winning character detail) doesn't she have a pimp when we meet her late in the movie after life has dealt her several horrible blows? My memory is unclear. [more about this performance at the 1946 Smackdown]
26th Academy Awards
Donna Reed in From Here to Eternity (1953)
Another arguable classification. While Reed's character is technically employed in the vague job of "hostess" at a social club in this Best Picture winner, the bestseller it's based on is clear that the character is a prostitute.
Jo Van Fleet as a Madame in "EAST OF EDEN"
28th Academy Awards
Jo Van Fleet in East of Eden (1955)
Young Cal (James Dean) thinks his mother is dead but he discovers she actually just chucked the domestic life when he was young and works as the madame at a brothel in this much-celebrated scene-stealing performance from Van Fleet.
31st Academy Awards
Best Actress Susan Hayward in I Want to Live (1958)
The Queen of 1950s Melodrama has been a very very bad girl (hooking ain't the half of her character's crimes)... and now she's on death row. To quote Rupert Everett in My Best Friend's Wedding "Oh the Susan Hayward of it all!"
33rd Academy Awards
Best Actress Elizabeth Taylor in BUtterfield 8 (1960)
While promiscuous party girl Gloria Wandrous (Taylor) is not technically a sex-worker -- she does scrawl "No Sale!" on the mirror in the opening sequence to make this point --the plot perpetually kicks around the notion that her boyfriend thinks of her as one and maybe, to her shame, she is starting too think that way about herself given the gifts she accepts and his suggestion that she could easily charge for her skills. A sex worker or merely, as she dubs herself, "the slut of all time"? You decide.
AND
Best Supporting Actress Shirley Jones in Elmer Gantry (1960)
This is the only Oscar year where both winning female roles are wild women who are either literal or figurative sex workers. [More about this performance at the 1960 Smackdown]
37th Academy Awards
Best Supporting Actress Lila Kedrova in Zorba the Greek (1964)
Kedrova is wonderful in this otherwise interminable drama as an old eccentric former courtesan. [More about this performance at the 1964 Smackdown with special guest Melanie Lynskey.]
Bree (Jane Fonda) with her former pimp (Roy Scheider) in KLUTE
44th Academy Awards
Best Actress Jane Fonda in Klute (1971)
Longtime readers will know that this is one of my all time favourite performances (and films). Fonda is utterly genius as a jaded callgirl whose life is threatened by a mysterious stalker. [A lot more about this film, scene by scene, in the Klute retrospective.]
53rd Academy Awards
Best Supporting Actress Mary Steenburgen in Melvin and Howard (1980)
A minor arguable entry in this company -- the fact that she's a stripper isn't a big deal part of the character. [More about this great performance at the 1980 Smackdown.]
68th Academy Awards
Best Supporting Actress Mira Sorvino in Mighty Aphrodite (1995)
A mix of two stock roles that haven't aged well: 'hooker with a heart of gold' and 'dumb blonde'. [More about this performance at the 1995 Smackdown.]
70th Academy Awards
Best Supporting Actress Kim Basinger in LA Confidential (1997)
In this neo noir classic, Basinger's "Lynn Bracken" is part of a Los Angeles stable of pricey girls who are hired or "cut" to resemble movie stars -- Veronica Lake in Lynn's case. [More about this performance at the 1997 Smackdown.]
Charlize Theron in "MONSTER"
76th Academy Awards
Best Actress Charlize Theron in Monster (2003)
In this wildly acclaimed performance, Theron stars as the real life life street prostitute Aileen Wuornos, who was executed by the state after being found guilty of murdering multiple johns.
80th Academy Awards... sex worker adjacent - Marion Cotillard won the Oscar as "Edith Piaf" in La Vie En Rose (2007). While Edith Piaf was not a prostitute, the movie does detail the fact that she was raised in a brothel
Anne Hathaway in LES MISERABLES (2012)
85th Academy Awards
Best Supporting Actress Anne Hathaway in Les Miserables (2012)
"Oh, Fantine, our time is running out... 🎵" This is the classic trope of prostitution as the last stop on a desperate womans journey to an untimely demise. [Oscar winning actresses in Musicals]
Emma Stone's second win for "POOR THINGS"
96th Academy Awards
Best Actress Emma Stone in Poor Things (2023)
Stone's inspired frankenstein monster Bella loves "furious jumping" and decides she might as well get paid for it, experimenting with life in a brothel before she's had enough of that transactional adventure. [More on Poor Things]
which brings us to the "now"
97th Academy Awards
Best Actress Mikey Madison in Anora (2024)
For the first time in history we have a case of consecutive sex worker roles winning in Best Actress. What do you make of that?
Now if you included nominated performances this list would be longer. Some famous examples (NOT A COMPREHENSIVE LIST) include...