Believe it or not, the last couple of installments for this series are coming, folks. As a reminder, this is a tradition I’ve been keen on for years. Yes, I’m ranking the new crop of Academy Award winners. For nearly all of the Oscar categories, you’ll see me list the top 25 recipients of that prize. Sometimes, our newest winner will appear. Other times, they’ll be relegated to the Honorable Mention category. Who knows, maybe one or two won’t even make the cut? It’s a list series that I’ll do each and every single year, in the weeks after the ceremony concludes. So, while this is a fun way to think about the Oscars in the aftermath of the latest telecast, it’s also a beginning for another column here on the site. Of course, definitely show us your own lists as well, in the comments section below. We’re definitely keen to know what you think!
Today brings the Best Actress category into focus. As you might imagine, there’s an embarrassment of riches here, and whomever you’re partial to, you won’t be alone. Hell, just with Frances McDormand, one of our most recent winner in Actress, she has three separate Oscars to choose from, all of which are high quality. You’ll be able to see where her win for Nomadland ranks below, but for me, tops in this category is Diane Keaton for Annie Hall, with Jodie Foster for The Silence of the Lambs and Hilary Swank for Boys Don’t Cry not far behind. Ironically, both Foster and Swank have other Academy Award wins in this category that rank highly for me, as you’ll see next, along with where our prior winner Jessica Chastain falls for her turn in The Eyes of Tammy Faye, as well as our newest champion in Michelle Yeoh for Everything Everywhere All At Once…
Here now are what I consider to be the 25 best winners of the Oscar for Best Actress, to date:

25. Brie Larson – Room
24. Shirley MacLane – Terms of Endearment
23. Julie Andrews – Mary Poppins
22. Kathy Bates – Misery
21. Cate Blanchett – Blue Jasmine
20. Helen Hunt – As Good As It Gets
19. Ellen Burstyn – Alice Doesn’t Live Here Anymore
18. Ingrid Bergman – Gaslight
17. Emma Stone – La La Land
16. Vivien Leigh – A Streetcar Named Desire
15. Jennifer Lawrence – Silver Linings Playbook
14. Michelle Yeoh – Everything Everywhere All At Once
13. Olivia Colman – The Favourite
12. Jodie Foster – The Accused
11. Frances McDormand – Fargo
10. Hilary Swank – Million Dollar Baby
9. Meryl Streep – Sophie’s Choice
8. Louise Fletcher – One Flew Over the Cuckoo’s Nest
7. Vivien Leigh – Gone With the Wind
6. Natalie Portman – Black Swan
5. Elizabeth Taylor – Who’s Afraid of Virginia Woolf?
4. Charlize Theron – Monster
3. Jodie Foster – The Silence of the Lambs
2. Hilary Swank – Boys Don’t Cry
1. Diane Keaton – Annie Hall
Honorable Mentions: Cher – Moonstruck, Jessica Chastain – The Eyes of Tammy Faye, Katharine Hepburn – Guess Who’s Coming to Dinner, Frances McDormand – Three Billboards Outside Ebbing, Missouri, Julia Roberts – Erin Brockovich, and Reese Witherspoon – Walk the Line

Stay tuned for the next category early on next week!
Hilary Swank in Boys Don’t Cry almost single-handedly keeps my belief that cis actors shouldn’t portray trans characters from being absolute.
Yes, I was wrong to defend the general practice in the past. Yes, I understand now that constantly casting cis actors in trans roles furthers the damaging perception that trans women aren’t “real” women and trans men aren’t “real” men, which can lead to literal acts of violence against them. Eddie Redmayne‘s nomination for The Danish Girl is one of the most unforgivable Best Lead Actor nods of the last twenty years. Studios and casting directors should just avoid doing it, and cis actors should, in nearly all cases, refuse to take on those roles if offered them.
But then… I’m reminded of Swank in Boys Don’t Cry, who is note-perfect in it. At no point does her portrayal undermine Brandon Teena’s identity or come off like a “costume.” It’s an exemplar of precise characterization with a true artist’s humanity. Honestly, one other reason cis actors should avoid trans characters is because there’s no way any of them can match what she did in that movie. The exception is also the peak.
Very well said!
My updated list I rewatched a lot of this past hyear including ones I have seen in years. I also have watched nearly every best actress winner with just a few to go .I added a few I had never watched before including Alice Doesn’t Live Here Anymore and A Touch of Class.
1.Anne Bancroft- The Miracle Worker
2.Sophia Loren – Two Women
3.Charlize Theron -Monster
4.Kathy Bates-Misery
5.Meryl Streep -Sophie’s Choice
6.Liza Minnelli -Cabaret
7.Julie Andrews -Mary Poppins
8.Ellen Burstyn -Alice Doesn’t Live Here Anymore
9.Michelle Yeoh -Everything Everywhere All At Once
10.Jessica Chastain -The Eyes of Tammy Faye
11.Julianne Moore -Still Alice
12.Judy Holliday -Born Yesterday
13.Frances McDormand -Fargo
14.Barbra Streisand – Funny Girl
15.Jodie Foster -The Silence of the Lambs
16.Claudette Colbert -It Happened One Night
17.Brie Larson -Room
18.Hilary Swank -Boys Don’t Cry
19.Renee Zelweger -Judy
20.Glenda Jackson -A Touch of Class
21.Sally Field -Norma Rae
22.Cher -Moonstruck
23.Simone Signoret -Room At The Top
24.Jodie Foster -The Accused
25.Marlee Matlin -Children of A Lesser God
HM
Olivia Colman -The Favorite
Halle Berry -Monster’s Ball
Jane Fonda -Klute
Katharine Hepburn -Guess Who’s Coming To Dinner
Maggie Smith -The Prime of Miss Jean Brodie
Vivien Leigh -A Streetcar Named Desire
Frances McDormand -Nomadland
Patricia Neal -Hud
Natalie Portman -Black Swan
Oops and Ingrid Bergman in Gaslight
Looks like I didn’t add Julia Roberts either I thought I had she would be somewhere in the middle of the list.
Always interested in these updates!
A top 40 would be easier it’s a challenge but I like doing it.
Oh for sure, more is always easier.