I always thought Annette's role in American Beauty was more supporting than lead- had she been in that category- she probably would have won.

There's also what I call the "I can do that factor". Remember, actors nominate actors; they always consider the degree of difficulty in a role. I bet many could see themselves or someone else playing Annette's role and doing it just a well or even better. Not the same with Hillary's - the character is very specific, rarely examined or attempted (if ever) AND a huge career risk . For those reasons, you could argue that there is no choice but to be in awe and reward such a performance.

I hope they win: - GLENN CLOSE - ANNETTE BENING - AMY ADAMS - JESSICA CHASTAIN - MICHELLE PFEIFFER - MICHELLE WILLIAMS - SIGOURNEY WEAVER

Love the Kate winslet and Jennifer Connelly reference. Jennifer getting snubbed instead of winning for Requiem for a dream and House of sand fog is the biggest crime ever.

It must be horrible to lose to the same person twice...

"Spacey, now better known for making Christmas videos"💀😂

Wonderful. I felt horribly for Bening when she lost to Swank, but I did agree that Swank was the most deserving (both times, actually). This video reminds me of two other Oscar races that had a similar vibe: 1) The 1950 race that gave Judy Holliday the win over Bette Davis (with most of the blame going to Ann Baxter, alas); and 2) Streep's win over Jessica Lange ("Frances"). Streep deserved it, of course, but in any other year, Lange would have been a near unanimous winner for her portrayal of Frances Farmer... she was literally that good! It's criminal that Lange's best performance ever is now almost completely forgotten by most serious film fans.

She should’ve gotten a nomination for film stars don’t die in Liverpool. What an amazing performance and good movie. 20th cent women also should’ve gotten nominated

FUN FACT: Madonna was supposed to be MUSIC OF THE HEART & was deep into pre-production with her violin training but dropped cause she & Wes Craven had "creative differences"

Hilary Swank also won because she had an impressive professional narrative. Everyone knew through previous interviews with Swank that she came from nothing and that her and her mother lived in their car for a while trying to make ends meet in California. She found acting, nurtured her craft from working class background, and found her way to Beverly Hills 90210 and the Karate Kid. She was seen as your typical young actor with a chance of a career with the followings of television and trendy sequels. With Boys Don't Cry, she showed that she was more than just a television dramatic actor, but one that could sell a feature film by name recognition and who portrayed a real person. The political climate was waking up to the realities of LBGTQIA+ life given the murder of Matthew Shepard in 1998, not to mention the professional outing and punishment of Ellen DeGeneres. The film told a story of a murder similar to Shepard's in association, and no one had any empathetic dramatic understanding of trans life on screen that didn't fall into heterosexist stereotypes of murderous drag queens and serial killer transgender folk. Hillary's empathetic portrayal of Brandon Teena wasn't a stereotype. Hilary found a real person for audiences to see transgender folk as real. While industry practice still struggles with authentic representation that even Kimberly Pierce said that she wanted a trans actor to portray Brandon, Hollywood box office insisted on someone with name recognition. To her peers in the Academy, this was seen as an artistic risk, as Hilary had minor name recognition. Sometimes going independent when you have some following, Hilary's being good television ratings and fair box office receipts, is enough to convince the Academy to vote for an investment of talent, especially seen in a new light. The Academy loves new performances like these. I think of Sally Field in Norma Rae as an example, and Sally had a harder climb considering the industry's attitude towards television. Hilary is a beneficiary of Sally's work. Hilary was the first of her young generation at the time to receive industry recognition this way. Reese Witherspoon would soon follow. That being said, Annette Bening was seasoned with her previous Oscar nominations, and for the longest time, it seemed that the Academy would not reward her on account of her being connected to Warren Beatty and not wanting to fall into industy nepotism. I would have felt a tie was necessary. Same with 2004. There is a chance that if Annette Bening does have the strongest performance in a "weak" year, she may win. Right now, it seems the Academy is remembering previously nominated well. But to be honest, I want Viola Davis to get Best Actress sooner than Glenn Close and Annette Bening. Viola has a lot more to prove in an industry that does not favor her skin color, whereas Glenn and Annette only have the age factor. I want all three to win, but the industry has to offer more opportunities for women of color, even though women of color may or may not have an easier time creating their own. thanks for reading this.

Swank gave one of the greatest performances ever captured on screen. She obviously couldn't play the role today, but 23 years ago... Boys Don't Cry changed and saved lives, no doubt about that. You don't really hear a lot of transgender people having issues with Swank. That's how important and groundbreaking the movie is. I admire Bening, should've won the Oscar for 20th Century Women.

Thank you very much for this video!!! Hilary Swank's win for Boys Don't Cry is hands down one of the most deserved victory in Oscar's history and easily in my Top 5 Best Actress wins. I find it interesting about your point about Annette Bening being cartoonish in American Beauty, I'm of the opinion that her character being the unlikeable 'nagging irritating wife' put her at a disadvantage against Swank who portrayed a sympathetic 'tragic figure' who also happened to be a real life victim. I think that was also a reason that swayed voters to vote for Swank alongside the sheer brilliance of her work as Brandon Teena.

Bening was actually fortunate to be even nominated. Her role was a supporting role in that movie

That loss for American Beauty must have been brutal for Bening who saw Spacey triumph over Washington and the film modestly sweeping the ceremony. But Swank was favored from the beginning with her winning all the critics awards and the Golden Globe. It was only SAG that snubbed her. If American Beauty had been placed in the Comedy/Musical category at the Globes, Bening could have gotten a bigger boost. But it also feels like her character and persona were turnoffs for the heavily male academy and yes, like you said her screen time was an issue. This also doomed Spaceck in 2001, Christie in 2007, and Davis in 2011.

Though everyone was concentrating on the deja-vu situation on the 2005 Oscars, I find that the best performance in that category was actually delivered by Imelda Staunton for her subtle portrayal of "Vera Drake".

This is the one I've been waiting for! Your breakdown for the reasons why Hillary won was amazing and makes so much sense. If an actor wants to be in the supporting category, would a studio allow it? I'm still waiting for a WOC to win lead actress but they have more luck in supporting but I don't want that to be the only option. It's a shame that Hillary's career hasn't blossomed the way it should after 2 Oscars but she's right, one in a lifetime roles are rare and she was fortunate that lightning struck twice

Really been enjoying your uploads so far, Brian. Def think your YT channel is on the verge of taking off!

Interesting observation about Tom Cruise. Made me realize hasn't attempted any Oscar worthy roles since Magonlia....I guess he gave up and would rather make money?

Amazing video! I think we all need one about 1951's best actrees for Judy Holliday over Gloria Swanson and Bette Davisñ

Let's talk about "Being Julia" for Benning- even for "Valmont" - she just has a presence that few can endure through a career. That is Talent to be recognized 👏

I agree that Swank’s performance are better than Bening in both years but i also love Bening and I’m really rooting for her long overdue Oscar win soon

Isabelle Huppert lost the Cesar 3 times for Isabelle Adjani before she won her first in 1995.

Great content! Well thought, well presented, well spoken!

Still wish Kate took it for this over The Reader😭

Hiliary swank deserves both awards

Both of the Oscars Hilary earned in my opinion, maybe some little more for Boys don't cry, that was such a huge mile stone in LMBTQ movie history plus the fact that an actress with then no celebrity status or Oscar history in an indie movie could make it, it's fascinating!

Annette Bening tamed the notorious Bachelor Warren Beaty, that’s way better than winning an Oscar

Oh wow! I love that you’re doing this! These are topics I’m incredibly knowledgeable about and never can really find anyone in my circle of people to geek out with. I’ve been following the Oscars and their history for almost 30 years! I remember this night very well! Such a great year of nominees. I had been ballsy enough to predict Swank for the win. She had the lion’s share of critics prizes, Critics Choice and the Golden Globe. Bening had SAG and BAFTA in a Best Picture contender. I think the passion for Swank’s performance was stronger than the steamroll zeitgeist. Which incidentally, how I viewed her 2004 win for Million Dollar Baby. But poor Annette. Someday… someday! Lito

love this series! hope this keeps going!

Hilary swank definitely deserved the first Oscar but the second time for million dollars baby? Either Annette or espacially Kate should’ve won their first Oscar that year

Great video! Hopefully, Bening will get an overdue Oscar soon. If you are interested in doing so, I would love to see your take on why Glenn Close hasn’t won an Oscar yet. She is possibly the most overdue actress we have!

OMG I immediately clicked as soon as this appeared in my timeline! Very explanatory and exhaustive, thank you so much. I'd probably add - and this is not to diminish your incredible essay at all! - that the reason why Swank won the 2nd time is that she had the strongest film, which not only won an Oscar for her, but swept that year's ceremony taking home Best Picture. Being Julia, a film I adore, wasn't widely seen as Million Dollar Baby was and, although Bening gives an astonishing performance as Julia Lambert, little could it do against such a giant hit like Eastwood's film. Yes, technically Swank managed to overcome that with Boys Don't Cry and ultimately win - but that was a dramatic, transformative performance, and we know how much AMPAS loves those performances. And Bening was the casualty of that. If that were up to me, I would give Hilary Swank (whose both Oscars are quite well-deserved) the Oscar for Boys Don't Cry and Bening the Oscar for Being Julia: it's such a good performance it's a study in brilliant acting, a completely unmissable one. I think the weight of having won 2 Oscars and the scarse options for great roles played a heavy part in Hilary Swank's career downluck. And Bening is in her 60s now: hopefully, they will both find good material and get back to work in great projects quite soon.

I watch be kind rewind a lot because I know a lot more about classic Hollywood and actresses more than I do current ones. Would you ever consider doing older Oscar category analysis? I've always wanted someone to do the 1950 Oscars. Although that's not very original, I would love to break down exactly why Gloria Swanson didn't win. Between that and saving private Ryan those are the 2 loses I have such a hard time understanding lol. Love your content.

Haley joel osment is still the most memorable of the five supporting actor roles

Bening should have been nominated and won for Film Stars Don't Die in Liverpool.

I might have preferred Kate Winslet in The Eternal Sunshine of the Spotless Mind ( one of my favorite movies) or Imelda Staunton in Vera Drake over Swank in Million Dollar Baby. Swank however was the right winner for Boys Don’t Cry it’s a cut above and is one of the all time best performances to win the Oscar. Good point that Annette Bening might have benefited from going to the supporting category it was that kind of performance that might have worked better in support. Time wise she is similar to Patricia Neal winning best actress for Hud but Annette was going to have a tough time against Hilary Swank that year for the kind of role Swank has and Swank absolutely deserved it. Supporting actress that year Annette or Toni Collette ( Sixth Sense) would be my preferences . While Jolie does a solid job it’s a performance that gets to be too much for me after a while sometimes less is more. That happens sometimes with a stand out performance it gets a lot of attention and praise but it wears a little thin.

Winslet deserved it this year. The MDB year. Swank absolutely did for BDC,

Let’s be real. The academy likes to feel as though they’re ahead of the curve when it comes to social issues and pat themselves on the back. As remarkable as Swanks performance is, I feel like it could have been less so and she still would have won.

BEEN WAITING FOR THIS. I've debated this actress race for my entire life. Well, Annette Bening's performance is one of my favorite, or favorite actress performances ever with Kevin Spacey being my favorite, but Hilary Swank was so good! I can't decide man. Anyway, GET ANNETTE BENING AN OSCAR TIME IS RUNNING OUT PLEASE GOD.

This subject is long overdue to be addressed about Benning v. Swank! I was more upset the second time around because "Being Julia" was Benning's best work, and utilized all of her talents as an actress. Boys Don't Cry was a transformative role for Swank, and made her an Academy Sweetheart. Personally, as a gay boy at the time, Boys Don't Cry was hard to watch and but Swank was perfect in that role; acting the role with dignity and viscerally. Love your insight and perspective addressed on this video! Looking forward to the next.

Swank deserved both of her wins. She was amazing in Boys Don’t Cry and Million Dollar Baby.

The scene where she hugs Lester’s clothes gets me every time. I always tear up. That was the moment that showed that Carolyn really loved Lester.

Janet McTeer was my second favorite performance of the nominees. Small indie film that cost about 3 times less than Boys Don't Cry to make

Oh I was very disappointed and upset to see Bening lose to Swank again! It must have been a wtf just happened night for Bening. I had been a huge fan hers since Bugsy, and I also loved her in American Beauty, The Kids are All Right, The Grifters, The Face of Love, 20th Century Women, and Being Julia which I thought it had all the ingredients of an Oscar winning role and performance. I feel that Swank was very lucky and got so much love from the academy that post Million Dollar Baby’s second Oscar, her career had gone downhill. I feel that Bening will get another shot at the Oscar next year with the biopic of Diana Nyad,

found channel and i LOVE IT!!! would love to see a video about Laura Linney and... timothee chalament... i feel Laura is so underrated.... and timothee has so many great movies but no Oscar...

“On the evening of February 27, 2005..” My birthday!! Also personally I think Annette Bening should have won for American Beauty, but congrats to Hilary. She was amazing in Freedom Writers!

Love your videos 🙌🙌🙌 glad that hillary won she was incredible. I love Annette Bening as she was also amazing in american beauty. honestly think she should of been put in supporting she doesn't have a ton of screen time especially compared to spacey, She probably would of won then or had a much greater chance.

Awesome job!

Imelda should won this year

I'm sure you were just reciting But Morris not Maureece (pronunciation) I know, whatever but I really loved that movie, 1 of 5 I believe.

“Now all that needs to happen is for Bening to win her first [goshdarn] Oscar!” Truer words have never been spoken.

The End of the Affair is one of my fave films of all time!

The Great Outdoors came out on June 17, 1988.

Thank you ❤

Imelda Staunton was hands down the best performance in 2004

Annette Bening🙄for sure. But Hilary Swank gave also an excellent performance. Either way, I don't believe Annette's career will suffer because of that. She will remain the ⚔tour de force that she is on the screen and 🤗delight us with many wonderful performances.

Janet McTeer won the Globe. She definitely had a shot, despite being the “dark horse” shot she still was in the race. NBR win too also helped the profile of a win for her.

I'm still waiting for 2 wins: Annette and of course Glenn

Such a close race! Especially with AB winning all of the other big 4. I think that Globe loss really did Annette in but Hilary deserved to win.

Whatever happened to Swank? Her last movie was a fatal attraction knock off. You gotta wonder what’s up with her.

I can't believe she did it twice. Both times it was Annette and second time. 23rd hour, out comes Million Dollar Baby 👶 though I think she was more apt to win for Being Julia, stunning performance

Boys dont cry is such a powerful movie

You should do an elusive Oscar vid for Bening. I wanted her to win for The Kids Are All Right, because she was an older actress and unless you’re Meryl Streep, it’s hard for an older actress to snag an Oscar and she gave a superlative performance in The Kids Are All Right.

Reese Witherspoon winning over Felicity Huffman in 2006 (I still don't get it) also would make a great video.

I love Hilary Swank, but I hope someday trans people can have more opportunities to tell their stories and showcase their acting talents. May that day come soon for someone like me.

20 years later, Annette keeps on working but...where has been Hillary Swank lately??? 🤔 in zero movies. An overrated actress, I watched 90210 and she was as mediocre as the rest of the cast. Annette was in the wrong category, her role is supporting actress in American Beauty and surely she would have beat Jolie

I would not have voted for Michael Caine for The Cider House Rules.

Can you please do glenn and olivia? Thank you

I absolutely disagree with your take on Swank's second Oscar. She's good in the film but, in all honesty, I can't say that she delivered a better performance than Imelda Staunton. Staunton's performance is one for the ages. It's absolutely stunning, honest, heartbreaking work by an actor at the top of her game. Swank is good but unremarkable.

So under rated, she is a marvelous actress. The grifters was fantastic and she just gets better and better.

I would be interested in someone braking down how Meryl has been nominated so much and won so little compared to say Hepburn or even McDormand and so on!!!

I adore Vera Drake. Imelda richly deserved to win.

I doubt that McTeer expected to win the Oscar even though British actresses who are not that well known in the US, e.g., Olivia Coleman can and do win. McTeer's Tumbleweeds is a riff on the similar movie with Susan Sarandon the title of which I have forgotten. The McTeer movie was far superior but doubtless is forgotten at this point. This is not to disparage Sarandon but point out that McTeer's script was superior. She is highly regarded in England and has appeared on the NY stage. Re Benning'g role in American Beauty as being a supporting role, the same could be said of Kidman's role in the Hours where she didn't spend that much screen time sharing it with two other actresses. I have only seen Swank in one movie, the title of which I can't remember; she certainly hasn't racked up a body of work for which she can be judged.

Annet bening must be supporting role in amarican beaty becase she was supporting♥❤♥

Same argument can be made for Close

great video, I agree swank was the better actress for Boys Don't Cry. but Swank winning for Million Dollar Baby really annoys me!!! I hated that movie

It's honestly hard to compare the two performances because they are both in wildly different films, being asked to do wildly different things. I love Annette Bening and her work in American Beauty was fantastic. Any other year, I would have said she deserved the Oscar hands-down. However, Hilary Swank's performance haunted my very being. In terms of career trajectory and comparing them both as actresses, I would say Annette Bening has more considerably more technique than Hilary Swank. When Hilary Swank is great, she is really really really great. But the rest of the time she is just ehhhhh (Freedom Writers, Black Dahlia, etc). Annette Bening is more consistently strong in her body of work.

Hilary Swank is Annette Bening's Eli Manning.

Annette should have won in American beauty she slayed that role

Don’t understand how Hilary swank won any Oscars I just think she was put in really good movies and got lucky there is no way that swank is better than Annette benning she’s unbelievable

matpat on the right of the thumbnail

I permit myself one unsafe prediction per year, and I called this one. It is consistent with Oscar tradition. Gender-bending and/or physical transformation. And it's clearly better! Meryl Streep looked more surprised than she ought to have been.

Annette Bening was robbed. Twice.

I guess the moral of the story is- it's about talent, but it's also partially about luck. Nobody was going to beat Hilary Swank in either of those amazing performances.

I still dont understand how the laughable Golden Globes is more prestigious than the SAG

I think Annette bening lost because she was seen more as a Supporting Actress than a Leading Role. Hillary swank deservedly won the Oscar. Jennifer lawrence(Silver linings playbook)defeats Jessica chastain(Zero dark thirty) Eddie redmayne(Theory of everything)defeats Michael keaton(Birdman or The unexpected virtue of ignorance) Mark rylance(Bridge of spies)defeats Sylvester stallone(Creed) Olivia colman(The favourite)defeats Glenn close(The wife) Anthony hopkins(The father)defeats Chadwick boseman(Ma rainey's black bottom)

Annette.

I think Viola Davis would have won in lead anyhow

your vids are catnip. more please!

How about a Oscar for Glenn Close 🤔

everything was going well until you questioned swank's second oscar... like wtf???? there was no competition she was the best.

The way Hollywood is, there's no question why Swank won

Bening should have won over Goldberg, period.

Bening was much better than Spacey.

Hillary Swank now make so bad movies, two Oscars don't help so much i think.

Waaaaaa . Incredible long career .. no statue waaaaaa acedemy awards are full of poop anyway

Hillary Swank didn’t deserve neither of her Oscars. 😒😒

I hate how Spacey's career was ruined. What a waste of talent. His only opportunity is christmas interviews, while Roman Polanski gets standing ovation. I mean was actually found guilty... Hypocrisy at its best.

It’s a shame. Annette Bening should have won both times