Let's continue our trek towards the top 20!
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#39 - Estelle Parsons, Bonnie & Clyde (1967)
You can't ignore that Blanche Barrow is an absolute terror in this movie. She is a whiny, petulant child who shrieks and screams her way throughout the story...and then at the end, you will very likely revel in the dose of karma she is given.
Blanche Barrow is absolutely annoying, there is no denying that...but Parsons gave the role what it required, and it is certainly effective.
I suppose the only downside might be that most of the role is presented in such a manner that is hard to find a lot of layers there, but it is really in her final moments once she realizes her husband ("Daddy") is going to die that the performance hits a strong emotional peak...and that is only topped further when she realizes she is losing her eyesight.
It is kind of crazy to think that Parsons became one of the only aspects of the film to win an Oscar that night considering the only other award it won was for Cinematography.
I do think Gene Hackman, who played Clyde's brother and Blanche's husband Buck, should've won in Supporting Actor too. I think this was a tough year though as I would've been more inclined to vote for The Graduate in a lot of other categories.
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#38 - Da'Vine Joy Randolph, The Holdovers (2023)
When a performance sweeps an award season, you sort of expect that performance to be undeniable. I think in the case of Da'Vine Joy Randolph, she benefitted from weaker competition and the fact that she played a character with unassuming gravitas.
Randolph's sweep was so epic that she pretty much won every single award for Best Supporting Actress during that award season, including most of the regional critics awards. I certainly don't consider this to be a weak performance, but it does baffle me a bit that she won pretty much everywhere.
Randolph plays Mary, a cook at an all-boys boarding school in New England who is still mourning the death of her son in Vietnam. Her demeanor to most seems to be a bit cold and aloof, but she does get along well enough with the highly unpopular Mr. Hunham (Paul Giamatti), a teacher known for being incredibly difficult as a grader and as a human being.
Like I mentioned before, Randolph's stature is one of gravitas. She is the strong, silent type who is willing to let some people in a little bit, but she is not always eager to do so. However, her most memorable scene occurs at a Christmas party when she gets drunk and has an emotional breakdown over her son's death.
This was definitely her Oscar scene, and it is the one that made her stand out the most amongst her fellow nominees. I actually first became familiar with Randolph back in 2012 when right of Yale, she got cast in the stage musical adaptation of Ghost in the role of Oda Mae Brown, the same role that netted Whoopi Goldberg an Oscar. Considering what a relative disaster that production was, Randolph was by far the best thing about it.
I do want to give a quick shoutout to Emily Blunt in Oppenheimer. For what was essentially a very small and underwritten role (which Nolan shafted both her and Florence Pugh in that), Blunt made me wish so desperately that she had a little more screentime because she commanded her moments to the point where she would own moments over co-star Cillian Murphy.
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#37 - Maureen Stapleton, Reds (1981)
I have always had a bit of a fascination with Emma Goldman as a historical figure, which stemmed from my introduction to her as a character in the E.L. Doctorow novel Ragtime and its musical adaptation.
She was a strong and feisty figure who did a lot for the cause of immigrant works and for pushing leftist values...so much so that the United States deported her.
Typical nonsense from a capitalist country...
So yes...a 3+ hour long film about the 1917 Russian Revolution might not excite everyone, but I am actually of the belief that Reds would've been a much better epic film for the Academy to embrace than other sluggish efforts like, say, Out of Africa or The English Patient.
Reds is a very long film and Stapleton's screentime isn't that much...but she truly makes an indelible impression as Goldman. It also doesn't hurt that she was considered rather overdue for an Oscar, and she managed to win for some of her finest work.
Stapleton gives the role the strong, wise, and feisty nature it needs. No better moment captures her personality than when Warren Beatty offers to walk her home late at night, so she is safe, but her response is: "Why? I won't hurt anybody!"
A truly wonderful win by a charismatic character actress.
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#36 - Dianne Wiest, Hannah & Her Sisters (1986)
I remember a few years ago, Wiest performed selections of Samuel Beckett for free in the Murray Hill Section of Manhattan. She stood in a fake rock reciting monologues by Beckett for anyone who cared to listen as they passed by. I managed to go see her briefly one of the afternoons she did it and I felt as though it was one of those moments, I truly couldn't believe I lived in this crazy city.
Wiest has such a sweet and neurotic energy that does seem prime for the world of Woody Allen...so it comes as no surprise that after her small but memorable supporting role as a prostitute in The Purple Rose of Cairo, Allen offered her the more substantial supporting role of Holly, one of the "her sisters" in Hannah & Her Sisters.
The dynamic portrayed between the three sisters has Holly as the kooky one who just simply doesn't have her life together, and while she doesn't get the same kind of arc that the other two do (aside from being one of the many women from the catalog of Woody Allen who is forced to act like she has fallen in love with him), Wiest just has such a unique and intriguing screen presence that you can't help but feel like you are watching an actress that is so singularly herself.
I do want to give a shout-out to her co-star Barbara Hershey, who plays sister Lee. Her work as the sister who is being pursued by Hannah's (Mia Farrow) husband Elliot (Michael Caine) should've been nominated for an Oscar as well.
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#35 - Ariana DeBose, West Side Story (2021)
The only issue is that I have a lot to nitpick when it comes to the how this story evolves.
Sure, it has its strong moments such as the score and the iconic choreography, but I just felt like I was never able to buy the full arc of Tony and Maria...and that she would be so willing to just quickly move on from the fact that he...umm...killed her brother Bernardo.
AND that Maria would have the gall to say to Anita, the girlfriend of Bernardo, that she should know better because SHE was in love.
YEAH. SHE WAS. WITH YOUR BROTHER. WHO WAS JUST KILLED BY THE BOY YOU JUST FUCKED.
So yeah...I have problems with all of this...
Anita as a character, however, is easily my favorite thing about West Side Story. Technically playing something of a counterpart to the Nurse character from Romeo & Juliet, Anita gives this musical so much life and when I heard that Broadway actress Ariana DeBose had been cast, I felt it was a truly inspiring choice.
She certainly didn't disappoint, but I do sort of hate that they sidelined her during the America sequence which would've really been a great way to truly give her a more bombastic moment to shine.
I honestly thought she was nearly as good as Rita Moreno, who also happened to win for the original movie...and she will be coming up shortly!
#34 - Patricia Arquette, Boyhood (2014)
It is always nice when a performer manages a comeback and then is able to sustain a strong career surge that lasts for quite a while.
Patricia Arquette always seemed to sort of be quietly in the background until she ended up winning a surprise Emmy Award for her work on the NBC drama Medium and then her work on Richard Linklater's passion project Boyhood led to an Oscar win and a slew of projects to follow.
I feel like Arquette may be the one to give the best performance in the film...although I am sort of inclined to say that Ethan Hawke also does as well...but Arquette manages to sell her role very well.
Arquette's Olivia is a single mother, and we basically get to watch her cope with raising a son all by herself...but for anyone who has seen or heard of Boyhood, you know the gimmick here is that Richard Linklater chose to film Boyhood over a period of 12 years as we watched young actor Ellar Coltrane naturally grow up over time.
Arquette never misses a beat with this motif. She has a quality that feels very eccentric and organic almost like a Sandy Dennis or a Geraldine Page and able to provide an abundance of vulnerability. It was such a treat to see her finally get this kind of recognition.
#33 - Mercedes Ruehl, The Fisher King (1991)
In some ways that are a little identical to Alicia Vikander, I feel like Mercedes Ruehl never exactly had a massive surge of popularity or major roles after her Oscar win...but she managed to work steadily and had great successes onstage in plays such as The Goat: or Who is Sylvia? and a memorable recurring stint on the show Fraser.
Ruehl is one of those performers, much like F. Murray Abraham, who really used their Oscar win to focus more on-stage endeavors. I honestly do wish more people had cast her in films over the years though because Ruehl is such a distinctive and truly captivating performer.
Think of her in something like 1988's Married to the Mob (for which she should've been nominated for an Oscar) and even that same year in Big, where she has the thankless role of playing Tom Hanks' mom and only gets a few scant scenes but somehow manages to create such a lived-in character.
Ruehl has been accused by some as being an actress who is normally a bit too broad in her acting approach...which probably extends to her being more comfortable as a stage performer...but I think a lot of what she does on film does work for the medium.
The Fisher King is an interesting film, and she is, to continue a frequent trend with these winning performances, one of the best things about it.
Her character of Anne is very blunt and has an edge, but she is also sort of warm and down-to-earth. She is never one to judge others and she has a very strong sense of self.
I suppose you could say she is a true fast-talking New Yorker through and through...and it is infectious. I just remember her scene where she is talking to Jeff Bridges about how women and God are so closely connected because both can create life...but then she admits: "the devil is a lot more interesting".
Ruehl herself is a lot more interesting as an actress than a lot of others can claim to be.
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#32 - Mercedes McCambridge, All the King's Men (1949)
I swear, I didn't put the two actresses named Mercedes together to try to be cheeky...but it just happened.
Mercedes McCambridge might be best known these days as being the actual voice of Pazuzu, the demon that possesses Linda Blair in The Exorcist. Her work went uncredited at the time and many actually assumed that Linda Blair did the vocal work herself which...looking back on it...seems far-fetched.
McCambridge's voice is very well suited for voiceover work...and just acting in general. It is deep and rich and very vibrant and she is used to strong effect in All the King's Men, a film that I can't say I love as a whole but does have its good qualities.
McCambridge gets to play Sadie, the secretary to Broderick Crawford's Willie Stark...and eventually she will become his mistress.
I should say ONE OF his mistresses, because Willie is a man-whore.
Sadie is no demure lady, however. I think it is that quality that truly makes McCambridge stand out because if this role had been played by an actress with a meeker stature such as Gloria Grahame or even a Celeste Holm, it might not have had the same brash and captivating effect that McCambridge was able to provide.
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What I WILL say is that I actually like this version of the film a lot LESS despite the legendary status it has...and a lot of that has to do with the rather horrible casting of Richard Beymer and Natalie Wood as Tony and Maria.
This doesn't even have to do with the fact their singing is dubbed. Wood manages fine iN some moments, but she is also...you know...in brownface since she is lily white.
Beymer, on the other hand, is so wooden and lifeless that I truly can't believe this is the guy who would go on to be the truly charismatic and problematic Benjamin Horne on Twin Peaks.
Moreno simply saves this movie and her ensemble from themselves.
Aside from them choosing for her to be dubbed during "A Boy Like That" as the song wouldn't quite sit well in her range, she did her own singing and dancing and she did a marvelous job with the assault scene (as did DeBose as well).
I do have to admit though that I would've been equally as happy if Judy Garland had won that year for her brief but immensely captivating work in Judgement at Nuremburg. That woman was a much better actress than many gave her credit for.
#30 - Celeste Holm, Gentleman's Agreement (1947)
In Gentleman's Agreement, she plays Anne, a NY Fashion Editor who manages to provide the film with moments of wit and charm...and she also steals the movie quite handily with her relatively minimal screentime.
As a film, Gentleman's Agreement does tend to teeter on the line of being a little too preachy and the ideas that Moss Hart tries to execute in his script (which revolves around a reporter posing a Jewish man to expose antisemitism in a post-WWII era) just don't truly seem to work as well he and director Elia Kazan might've liked to believe...and Kazan, of course, had his own bigoted prejudices but I will sort of address that when I discuss the win of Eva Marie Saint coming up.
Holm's Anne brings so much light into the film, especially because her two leading co-stars Gregory Peck and Dorothy Maguire have little to no chemistry or life in any of them.
The success of Anne as a character is also the film's greatest success because the "message" of the movie doesn't become as preachy through her words/actions. When Holm has a chance to shoot down antisemitic comments, it comes off as a genuine expression whereas the rest of the film could be considered something of an "ethnic savior" film...or as "Stevie" on Letterboxd called it: "a gentile savior film" that simply needed maybe another rewrite.
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#29 - Tatum O'Neal, Paper Moon (1973)
I decided to give O'Neal more credit in this case, because if I am being honest, I am not even sure how I feel about her winning this. O'Neal holds the distinction for being the younger performer of any gender to win an Oscar...and it is also in strong contention of being the biggest case of category fraud in Oscar history, too.
It has also been heavily documented that this was a performance that was heavily coached and influenced by its director Peter Bogdanovich to the point where it was truly staged to every last detail.
I will admit that despite that aspect, the role comes off a lot more natural than it could have...and she does manage to steal the movie from her own father who...it must be said...isn't exactly the finest actor to have come out of Hollywood.
Considering the rather rocky relationship those two have had, I do find it kind of hilarious that she was able to show him up at such a young age.
If I am being honest though, I kind of wish O'Neal's co-star Madeline Kahn would've taken this win. I decided to give O'Neal more credit in this case, because if I am being honest, I am not even sure how I feel about her winning this.
O'Neal holds the distinction for being the younger performer of any gender to win an Oscar...and it is also in strong contention of being the biggest case of category fraud in Oscar history, too.
It has also been heavily documented that this was a performance that was heavily coached and influenced by its director Peter Bogdanovich to the point where it was truly staged to every last detail.
I will admit that despite that aspect, the role comes off a lot more natural than it could have...and she does manage to steal the movie from her own father who...it must be said...isn't exactly the finest actor to have come out of Hollywood.
Considering the rather rocky relationship those two have had, I do find it kind of hilarious that she was able to show him up at such a young age. If I am being honest though, I kind of wish O'Neal's co-star Madeline Kahn would've taken this win.
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#28 - Ruth Gordon, Rosemary's Baby (1968)
"I can't tell you how encouraging a thing like this is!" - Ruth Gordon during her acceptance speech
After years of fleeting moments of success as a character actress and also working with her husband Garson Kanin as a screenwriter, Ruth Gordon managed to win an Oscar for a role in a horror film.
Even those who hated Rosemary's Baby had expressed in their reviews that they supported the idea of her winning...but I certainly didn't hate this movie.
In fact, I love this movie and think it was robbed of nominations for Best Picture, Director, and Actress for Mia Farrow.
Gordon's role of Minnie Castavet is something of comic relief for the movie and her energy is certainly a lot of fun in its own busybody way, but it becomes all the creepier when you realize she and her husband are wanting Rosemary to bear the antichrist into the world.
It was an inspired choice to take the Oscar and I am glad it allowed Gordon to have such a strong resurgence in her career which led to her other amazing performance in the 1971 cult classic Harold & Maude.
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#27 - Marisa Tomei, My Cousin Vinny (1992)
"Imagine you're a deer. You're prancing along. You get thirsty. You spot a little brook. You put your little deer lips down to the cool, clear water....BAM! A fucking bullet rips off part of your head! Your brains are laying on the ground in little bloody pieces! Now I ask ya...would you give a FUCK what kind of pants the son of a bitch who shot ya was wearing?!"
And THAT, my friends, is comic gold and this is easily one of the most inspired Oscar wins from any acting category in their history.
It seemed so inspired and so out of left field that snarky film critic Rex Reed (that bitch...) was thoroughly convinced that actor Jack Palance somehow read the wrong name...and this theory wasn't helped by the fact that Jack Palance was acting like a freaking space cadet the whole time leading up to him opening the envelope.
As evidenced with the La La Land/Moonlight debacle, the accountants from Price Waterhouse Coopers WILL step forward if something is incorrectly announced as the winner.
This was a case where Tomei benefitted from competing against 4 mostly dramatic performances from 3 British actresses and 1 Australian actress making her the only American. On top of that, she had received no prior precursor support...so this seemed like a win that truly did come out of nowhere and I still think it is one of the most baffling.
Even though I MIGHT have voted for Judy Davis in Husbands & Wives over her, I have to commend the Academy for this selection as Tomei is an absolute riot in My Cousin Vinny. It is certainly a performance that is remembered today and despite the age difference, she and Pesci work surprisingly well together.
My Cousin Vinny is a solid comedy film, but there is something to be said for the delicious comedic work done here by Tomei and she manages to make the film even better.
Thankfully, she has proven her worth as an actress in the years since with dramatic work in movies like In the Bedroom and The Wrestler.
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#26 - Juliette Binoche, The English Patient (1996)
When Kevin Spacey opened up the envelope, it seemed as if the whole world was practically ready to put a crown onto Lauren Bacall's head and call her "Queen of Acting".
But hold on...the envelope said Juliette Binoche in The English Patient.
Bacall was PISSED off...and it was such a "lock" that Binoche even said from the stage that "I thought Lauren was going to get it...and I think she deserves it".
In hindsight, Bacall's work wasn't that remarkable in the even lesser film that was The Mirror Has Two Faces...but considering how The English Patient swept that night, it doesn't come as a shock that Oscar voters would've wanted to honor it with an acting win.
Frankly...I would go as far to say that Binoche is (and I have said this about many of these performances) the best thing about her movie.
The English Patient is a chore to sit through. It looks beautiful, it has a good ensemble of actors, but it still remains the only movie I managed to fall asleep during TWICE...and during broad daylight.
I like to think of myself as someone with a strong attention span...hell, I love Ingmar Bergman movies! Still though, my vitriol for The English Patient isn't as intense as it used to be...and even when it was, I always acknowledged that Binoche was truly the heart of the film.
Her scenes caring for the severely burned Ralph Fiennes are very touching and I still often think of her delivery of the line as she reads from one of Fiennes' books: "The heart is an organ of fire...I like that...I believe that".
It also doesn't hurt that I think she is owed an Oscar after being snubbed for far superior work in movies like Blue and Certified Copy.
I do want to give a shout-out one other person in her category though whom I felt would've been an equally worthy winner (who also happened to be more of a lead like Binoche), and that was Marianne Jean-Baptiste from Secrets & Lies.
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#25 - Olympia Dukakis, Moonstruck (1987)
There are certain actresses I have a fondness for because they just seemed to pop up in a lot of things I either watched or saw my mother watching as a kid.
Olympia Dukakis is one of those actresses...and aside from her work in movies like Mr. Holland's Opus, Steel Magnolias, and Look Who's Talking, I remember my grandmother really being obsessed with Moonstruck. It was one of her all-time favorite movies and, I have to admit, I do feel very fond of it, too.
Dukakis' Rose gets to be the doting and dry-witted mother to Cher, but she also has to deal with her wandering husband at the same time. In a way, John Patrick Shanley including this plot point for Dukakis was a masterstroke as it gave her so much more to play.
Her scenes with John Mahoney at the restaurant are perhaps what really drive her performance home for me, and by the end, you admire and respect her decision when she decides to give her husband another chance.
I had the chance to meet Ms. Dukakis not long before her passing. She lived in the West Village where I worked at the time, and I had developed a friendship with a fellow actress who worked with her on Tales of the City.
She, despite approaching 90, was sharp as a tack and so appreciative of how much I wanted to talk to her about her work. I will always feel sentimental about this performance and her as an actress and as a person.
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#24 - Eva Marie Saint, On the Waterfront (1954)
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#23 - Anna Paquin, The Piano (1993)
After Tatum O'Neal, the second youngest performer to win an Oscar was Anna Paquin...and sure, this is a case where Paquin was obvious far too young to understand what was going on around her...but whatever Jane Campion did with her was magical.
Unlike O'Neal, Paquin is truly a supporting player in the film and is often in the background of many scenes...but she provides such a fascinating energy whenever she is brought to the forefront.
The moment when she speaks of her mother's mute nature is a particular highlight. The lyrical nature of which she delivers this monologue gives off a "wise beyond her years" vibe when she talks about how her mother witnessed the death of her husband: "At the same moment my father was struck dead, my mother was struck dumb...she never spoke another word."
There is something so haunting about her, and she is even something of a villain to the piece as she seems to set in motion the potential demise of her mother's dreams.
Going into Oscar night, many expected that Winona Ryder would win for The Age of Innocence, but I think the Academy made the right choice in this case.
Paquin gives one of the greatest child performances ever captured on film; there is something just so captivating about her and the otherworldly energy she has.
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#22 - Peggy Ashcroft, A Passage to India (1984)
I am not saying that A Passage to India should've won the Oscar for Best Picture, but I do find it kind of hilarious to the Academy only seems to honor overlong bloated epics when they are normally more of a chore to sit through (see Out of Africa winning the following year).
I do remember liking A Passage to India even if it did feel like something of a lesser film in the canon of David Lean...a pretty tall order when you are in a filmography that includes Brief Encounter, The Bridge on the River Kwai, and Lawrence of Arabia.
Peggy Ashcroft was the beacon of the film and sadly, I feel like no one really discusses her these days. She passed away in 1991, but I think the real reason for this is that her career had been mostly confined to the UK and was spent on the London stage doing everything from Shakespeare to Brecht to Pinter to Beckett.
Even my knowledge and familiarity with Ashcroft is fairly limited and I haven't seen her in much of anything...but I think her work in A Passage to India shows that she could've easily translated to a reputable film career had she wanted it.
I actually feel that Ashcroft should've been placed in the Lead category, which that year was very weak and allowed for Sally Field to win a second Oscar for relatively middling work in a middling film.
With Ashcroft in lead, I would've dreamed for one candidate to slip into the race to win for Supporting Actress: Nastassja Kinski for Paris, Texas.
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#21 - Catherine Zeta-Jones, Chicago (2002)
The film adaptation of Chicago came along at a time when movie musicals were simply not in vogue...but the year prior to its opening, Moulin Rouge more or less paved the way for the musical genre to make a comeback.
Chicago has had an interesting history as a stage show. When it opened in 1975 on Broadway, it got eclipsed by A Chorus Line which would go on to become the longest running musical in Broadway history when it closed in 1990. Chicago, on the other hand, closed in 1977.
Fast forward to 2002 when the film version of Chicago opens.
By now, Chicago has a scaled down revival on Broadway that had been open for 6 years and a movie version was now in the works. At first glance, the casting of Zellweger and Zeta-Jones as Roxie and Velma, respectively, does seem a little strange.
They are both younger than the characters were originally written and neither were known for being musical performers...but the reality is that Zeta-Jones had the experience in doing musical work on the stage and IT SHOWS.
Upon rewatching Chicago a couple of years ago having not seen it in over a decade, I did find myself still impressed by how well the film had up (even if I don't think as highly of it as I used to) and a lot of that power was due to Zeta-Jones.
She gives a performance that is truly electrifying pretty much every single moment she is onscreen. While you can say she starts off the film on a high note with "All That Jazz" or stands out as part of the "Cell Block Tango" ensemble, I always come back to her showcase "I Can't Do It Alone".
A truly legendary film musical performance that is worthy of all the acclaim it has received.
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THOUGHTS BEFORE THE TOP 20:
What a strong group of actresses and performances. The talent on display here is clear to see, and even if some of them may not have gotten my personal vote in the end, I do like or even love a lot of these performances on their own merits.
I feel very good about my top 20, but I will say that some of the order may shift around a bit. It'll be a bit of a bloodbath, but I do consider the top 20 (and even my top 40) to be a true celebration of these amazing actresses.
For the other volumes in this ranking, please see the below links:
*Vol. 4 - The Top 20*
