Here is a new update. The newly added performance is highlighted in bold.
1. Vivien Leigh in Gone with the Wind (1939)
2. Luise Rainer in The Good Earth (1937)
3. Jessica Lange in Frances (1982)
4. Gloria Swanson in Sunset Boulevard (1950)
5. Olivia de Havilland in The Heiress (1949)
6. Maggie Smith in The Prime of Miss Jean Brodie (1969)
7. Anne Bancroft in The Graduate (1967)
8. Janet Gaynor in Seventh Heaven (1927-1928)
9. Jill Clayburgh in An Unmarried Woman (1978)
10. Glenn Close in Dangerous Liaisons (1988)
11. Geraldine Page in The Trip to Bountiful (1985)
12. Susan Sarandon in Thelma & Louise (1991)
13. Katharine Hepburn in Suddenly, Last Summer (1959)
14. Edith Evans in The Whisperers (1967)
15. Norma Shearer in Marie Antoinette (1938)
16. Greta Garbo in Ninotchka (1939)
17. Faye Dunaway in Bonnie and Clyde (1967)
18. Hilary Swank in Million Dollar Baby (2004)
19. Cate Blanchett in Elizabeth (1998)
20. Nicole Kidman in Moulin Rouge! (2001)
21. Kate Winslet in Eternal Sunshine of the Spotless Mind (2004)
22. Simone Signoret in Room at the Top (1959)
23. Bette Davis in The Little Foxes (1941)
24. Julie Andrews in The Sound of Music (1965)
25. Rosalind Russell in Auntie Mame (1958)
26. Glenda Jackson in Women in Love (1970)
27. Joanne Woodward in The Three Faces of Eve (1957)
28. Elizabeth Taylor in Suddenly, Last Summer (1959)
29. Renée Zellweger in Bridget Jones's Diary (2001)
30. Barbara Stanwyck in Ball of Fire (1941)
31. Sissy Spacek in In the Bedroom (2001)
32. Halle Berry in Monster's Ball (2001)
33. Lee Remick in Days of Wine and Roses (1962)
34. Annette Bening in American Beauty (1999)
35. Diane Lane in Unfaithful (2002)
36. Emily Watson in Hilary and Jackie (1998)
37. Judi Dench in Iris (2001)
38. Julie Christie in Away from Her (2007)
39. Shelley Winters in A Place in the Sun (1951)
40. Audrey Hepburn in Wait until Dark (1967)
36. Emily Watson in Hilary and Jackie (1998)
37. Judi Dench in Iris (2001)
38. Julie Christie in Away from Her (2007)
39. Shelley Winters in A Place in the Sun (1951)
40. Audrey Hepburn in Wait until Dark (1967)
41. Meryl Streep in The Devil wears Prada (2006)
42. Ingrid Bergman in The Bells of St. Mary’s (1945)
43. Julie Walters in Educating Rita (1983)
44. Anne Baxter in All about Eve (1950)
45. Judi Dench in Mrs. Brown (1997)
46. Helen Hayes in The Sin of Madelon Claudet (1932)
47. May Robson in Lady for a Day (1933)
48. Jane Fonda in Coming Home (1978)
49. Greer Garson in Goodbye, Mr. Chips (1939)
50. Doris Day in Pillow Talk (1959)
51. Meryl Streep in One True Thing (1998)
52. Joan Crawford in Sudden Fear (1952)
53. Deborah Kerr in From Here to Eternity (1953)
54. Katharine Hepburn in Guess who’s coming to dinner (1967)
55. Marsha Mason in Chapter Two (1979)
56. Jane Wyman in The Yearling (1946)
57. Melissa Leo in Frozen River (2008)
58. Martha Scott in Our Town (1940)
59. Teresa Wright in The Pride of the Yankees (1942)
60. Jennifer Jones in Love Letters (1945)
61. Ellen Burstyn in Same Time, Next Year (1978)
62. Susan Hayward in My Foolish Heart (1949)
63. Jeanne Crain in Pinky (1949)
64. Eleanor Parker in Detective Story (1951)
65. Vanessa Redgrave in Mary, Queen of Scots (1971)
66. Diane Keaton in Marvin's Room (1996)
67. Louise Dresser in A Ship comes in (1927-1928)
68. Dorothy McGuire in Gentleman's Agreement (1947)
69. Loretta Young in Come to the Stable (1949)
70. Mary Pickford in Coquette (1928-29)
71. Leslie Caron in Lili (1953)
72. Sissy Spacek in The River (1984)
73. Shirley MacLaine in The Turning Point (1977)
74. Irene Dunne in Cimarron (1930-1931)
75. Ruth Chatterton in Madame X (1928-29)
76. Diana Wynyard in Cavalcade (1932-1933)
77. Bette Davis in The Star (1952)
Leslie Caron as Lili Daurier in Lili
When I reviewed Leslie Caron’s Oscar-nominated performance for the first time, I was not overly impressed with her work but still found enough to like to be generous in my overall grade. As you can see from my ranking now, my opinion on her work has definitely lessened now which is why I will write a few words in this case.
The main problem of Leslie Caron’s performance and the reason why I downgraded her work mostly to be found in the character she is playing and the movie she is in. Obviously, I always separate the work of an actress from her surroundings if she is able to overcome them or work effectively within them - which is something that Leslie Caron actually does but there are limits to what an actress can achieve if the task she is given is so ridiculous from the start that there is simply no way to save the material she is given in any way. Or rather, to raise it to a level that I would expect from an Oscar-nominated performance.
What surprised me extremely when reading about Lili on the Internet is how many people seem to love this movie and how even usually cynical Oscar bloggers write how it is one of the most lovely surprises in their Oscar journey. But to be fair, even I became a victim to Lili’s easy likability when I watched it for the first time, calling the movie charming, innocent and harmless. And even now I can understand why I had that opinion and why so many others have it - if you watch the movie without thinking too much, it is very easy to get lost in it. It follows its story with serious dedication and presents every character and plot very straight-forward despite being an almost fairy-tale like situation and even now I occasionally crack a smile when I see Leslie Caron and the puppets sing the catchy tune “Hi-Lili, Hi Lo”. But re-watching it now and thinking more deeply about the story and its central character, everything immediately falls apart for me. And no matter how dedicated Leslie Caron is in her role, she cannot save the unsavable task of making sense of Lili the movie or Lili the character. 
The major problem with Lili as a character is that the movie needed a female role who was young enough to believe that hand puppets are actually talking to her but also old enough to decide that she wants to enter a toxic relationship of verbal and physical abuse for the obligatory “happy ending”. The screenwriters seemed to think that 16 is the ideal age in that case and so we have 22-year old Leslie Caron playing a 16-year-old with what appears to be the intellect of a 4-year-old. To be fair, Leslie Caron actually managed to be convincing as a 16-year-old and whatever she has to do in her role, she does it with complete earnestness but also the necessary light charm, might it be following a man she hardly knows around town or talking to the puppets about her private thoughts. But still, how could any actress make sense of all of it? Again, if you only watch Lili for being charmed, then it succeeds and you will leave the movie marveling about Leslie Caron but when you think about it on an Oscar-level and begin to ask what Leslie Caron really did here, then you are lost. 
The story of Lili, despite its childish atmosphere, is actually very dark - Lili suffers from the death of her father and the man she hoped who would help her, is almost abused by the first man she meets, contemplates suicide and is constantly verbally and phyisically abused by the man who controls the puppets that she loves so much. And there is probably a lot to interpret in the story, finding a young woman’s sexual awakening and coming-of-age, people who are only able to communicate via puppets and without seeing each other but again - underlying themes become basically meaningless if the message is brought across so ridiculously.
Leslie Caron’s character is the kind that would nicely be described as “naive” or “helpless” but watching her scream in the middle of the street when she sees an acrobat and follow basically everyone around who talks to her makes you wonder how she even managed to survive one day after the death of her father and how she rather resembles a child of 4 in the body of a young woman. It’s not enough that she earnestly interacts with the puppets and seems to believe all the time that they are real - even after she is hired at the circus as part of the puppet act and she knows that a man (who is constantly angry at her as a way to hide his feelings of love for this girl of 16) is controlling them and people are watching her, she still interacts totally seriously with them, constantly “forgetting” that they are not real. And even at the end, when she wants to leave the circus (claiming that she has grown up and is wiser now), she still says goodbye to them as if they are real people. Again, Leslie Caron gives all of this the most possible amount of dignity but there is no way she can make any sense of any of it or give any depth or complexity to Lili as a character. She has absolutely zero chemistry with Mel Ferrer and for some reason the movie makers want us to cheer the fact that she ends up running into his arms even though they never shared a single loving moment and he only attacked and even slapped her during the movie. More than that, how comfortable can a love story be when the man in question knows that the woman he loves is basically a little girl who talks to hand puppets and buys candy and dolls when she has a little money? And even if we forget Lili’s “naivety”, she still remains a 16-year-old girl, so her ending the movie with the obligatory kissing moment still feels wrong for basically every reason. 
Again, all of these are complaints about the movie and the screenplay (that somehow won a Golden Globe and a WGA award) but it just underlines how Leslie Caron has nothing to work with. I understand that Lili seems to have been a big deal back then, scoring various major Oscar nominations and also winning Leslie Caron a BAFTA - I suppose the whole concept of an actress talking to hand puppets and making it believable was for some reason new and artistically exciting. And I want to be fair to Leslie Caron and say that more than anything, this is a misdirected performance for me rather than an actress not being up to the task she was given - but even this statement is a bit contradictory because at the end of day, Leslie Caron did exactly what she had to do to make Lili a success: being a charming presence and making Lili as a person believable in the context of the story. And this is what she did, bringing the fairy-tale aspect of the story to live, but this fairy-tale did not allow her to go deeper in any way. Again, I applaud her for being so serious in her role and as I said before, if you only want to be charmed, then she succeeded in her role. But thinking closer about her character, there is simply nothing to build on or to use and at the end of the day, all she has are a few scenes talking to puppets, crying or being sad (and not even her obligatory two dancing scenes impress in any way). She is quite touching when she drops the watch of her father and has a moving moment when she asks Marcus "What shall I do now?" after losing her job as a waitress but the effect of such a scene is ruined when you remember that the only reason why she lost her job was her not working and only starring at Marcus, another moment when the movie wants us to present Lili's strange behavior as "charming naivety". On the other hand, she never evokes any true emotions outside of scenes that ask her to and even then she sometimes fail - she tells the story of her father's death without any visible feelings, despite the fact that his death is the reason for all her troubles and noting bad that happens to her seems to have any effect on her character. The truth is that even the most talented actress could not combine the different aspects of Lili (believing in puppets, falling in love with an abusive man, beginning to understand the world around her) into one coherent character and so Leslie Caron is never able to explain Lili as a human being, why she behaves the way she does, what she thinks and wants, why she would fall in love with Paul and she never explores (or isn't allowed to explore) the darker tones of the story (while Mel Ferrer on the other hand goes too far in exploring them, making his performance unnecessarily dark and unlikable, making it even harder for Leslie Caron in the process of make her affections believable) and as an actress seems just as lost as Lili is as a character.
