1953: Audrey Hepburn for Roman Holiday

In her first starring role, soon-to-be screen icon Audrey Hepburn plays a princess on a tour of Europe. Fed up with schedules and duties, she escapes from the embassy in Rome, and, as fate would have it, runs into a reporter in need of a scoop. He gives her the fun day she's always wanted, but will she discover his identity?

It's difficult to imagine a world in which no one knows who Audrey Hepburn is. Most people my age who don't even watch old movies have heard of Audrey Hepburn. But before this movie, her name was only vaguely familiar to a few people. It was her performance as Princess Ann that made her famous, with good reason. She demonstrates an extraordinary degree of natural talent in this rather unusual role. She has to play regal and dignified, but at the same time likeable and relatable to the average audience member, and she is brilliant at both. It's no wonder she became one of the most well-known movie stars of her time. I don't think this is my favorite Audrey Hepburn film, but it's still pretty wonderful. It certainly provides a perfect introduction to her, since it lets her demonstrate a wide range of skills.

For example, she displays excellent comedic timing, especially in the scene toward the beginning when she's been drugged. But she's also perfectly capable of playing it straight and letting someone else be the funny one when it's called for, letting Gregory Peck and Eddie Albert joke around her while she is seemingly oblivious. Then there's the extremely wide range of emotions she effectively portrays: hysterical, bored, upset, overjoyed, nervous, terrified, amorous, determined, the list goes on and on. The movie seems simple and straightforward, yet her character is anything but. Somehow she makes it look easy. I've watched this a few times before, and I never fully appreciated just how challenging of a role this must have been. Hepburn pulls it off like a seasoned actress, not at all like the novice she was. It's less surprising now, knowing all of the other great performances she would give soon afterwards, but it must have been shocking to audiences of the day that a young newcomer could hold her own against an established star like Gregory Peck. So appropriately, she was given an Oscar.

This was Hepburn's first of five Best Actress nominations, and her only win. She was nominated the following year for Sabrina, then for 1959's The Nun's Story, 1961's Breakfast at Tiffany's, and 1967's Wait Until Dark. She was also awarded the Academy's Jean Hersholt Humanitarian Award after her death in 1993, for her work with UNICEF. She was also the fifth person to have won a competitive Emmy, Grammy, Oscar, and Tony, though the Grammy was awarded posthumously. She was a tremendously talented, generous human being, and if you only know her as a style icon, you're missing out. Everyone should definitely see at least one of her movies besides Breakfast at Tiffany's, and her Oscar-winning performance is a good place to start.

Coming up next: Grace Kelly, in an Academy decision that Judy Garland fans are still upset about

1952: Shirley Booth for Come Back, Little Sheba

Booth plays Lola, a frumpy, childless housewife married to a recovering alcoholic. Her relatively boring life suddenly becomes much more exciting when a beautiful young college student moves in with them.

I did not have high expectations for this movie, for several reasons. First, I'd never heard of it before, and I feel like by now I've at least heard of most great films, especially from this era. Second, it has a really cheesy title. Third, it was from 1952, the year the Academy picked a stupid circus movie for Best Picture (no, I'm still not over it). Fourth, I didn't really know who Shirley Booth was. So I was certainly not expecting this to be one of the best performances I've seen so far, but I'm pretty sure that it was.

This was Booth's film debut, but she had won a Tony two years earlier for playing this role on the stage. I can certainly see why; she embodies this character so perfectly, I can't imagine anyone else playing her. Within the first couple of minutes of the film, I felt like I knew her. While I found out more about her as the story progressed, everything I learned was consistent with how she acted from the beginning. This character has such a pathetic life, but she tries, rather unsuccessfully, to pretend she doesn't. Booth does a tremendous job of keeping all of Lola's pain and fears and regrets just barely below the surface. It would have been a completely different story if her lines had just been read the way they appeared on paper. Lola could have just seemed annoying for prattling on all the time, but you can tell she's only doing it as a cover to convince herself that everything is all right, and it's heartbreaking.

It's worth mentioning that all the other performances in this film are very good, too. Terry Moore was nominated for Best Supporting Actress for her charming portrayal of the young college student. I was also impressed by Burt Lancaster's performance as the alcoholic husband. He gets some criticism for being way too young for the part - it's implied that he and Lola are about the same age, when Lancaster was in fact 15 years younger than Booth - but I think that actually works. It helps explain some of the characters' frustrations that she appears to have aged much faster than he has. Even Richard Jaeckel's complete jerk of a character was very well-played. But Booth unquestionably steals the film. Rarely have I been so moved by a performance as I was by this one. I believed in her sadness so completely that I desperately wanted to give her a hug and be her friend; anything to make her truly happy for just a minute. Apparently Booth's first husband was an alcoholic womanizer, and her second, much nicer husband had recently died suddenly, so she certainly had plenty of pain from her actual life to draw from. Perhaps that's why her performance is so convincing. Or maybe she was just an extraordinarily talented actress. Regardless, you should definitely check out this movie if you haven't seen it. While it does come across as more of a play than a movie, it's an incredibly well-performed play that's unquestionably worth watching.

Shirley Booth was only ever in a few movies, which probably explains why I didn't know who she was. She did most of her acting on the stage or television. Now she's most well-known for playing the title role in the 1960s sitcom "Hazel," which is something else I'd never heard of before. Anyway, this was her only Oscar nomination, but she also won two Emmys and three Tonys, which I would call a pretty impressive resume. Also she lived to be 94 years old, which is also pretty impressive. But nothing's more impressive than her performance in Come Back, Little Sheba. Seriously, I cannot stress enough how blown away I was.

Next up: Audrey Hepburn

1951: Vivien Leigh for A Streetcar Named Desire

In her second and last Best Actress winning performance, Vivien Leigh plays Blanche DuBois, a schoolteacher on the verge of a psychotic break who moves in with her sister and abusive brother-in-law in their tiny New Orleans apartment.

This is one of those movies that is extremely well-done but not at all fun to watch. It's just so incredibly disturbing. Also I think it's difficult for modern audiences to understand because a lot of important plot points are heavily veiled due to production codes. I had only seen this movie once before, seven years ago, and I'm pretty sure I didn't really understand what was going on. I remembered very little about it apart from Marlon Brando famously bellowing, "STELLAAAAAAAAAA!" So even though it's far from my favorite film, I'm happy I watched it again because the first time I completely missed how amazing Vivien Leigh was.

The character of Blanche DuBois is extremely complicated, in a way that seems like it would be ridiculously difficult to convincingly portray without going too over-the-top, but Leigh pulls it off flawlessly. Blanche has several different go-to "modes", for lack of a better term, and Leigh changes her face, voice, and demeanor to fit each one. There's the flirtatious, fake-happy, lying-through-her-teeth Blanche, who reminded me a lot of Scarlett O'Hara. This is clearly her mask, the way she desperately wants others to see her, and the way several characters do see her, but she makes the mask thin enough that the audience can mostly see through it. When she feels comfortable enough, she consciously gives other characters a peek beneath the mask, and that's when she seems the most relaxed and natural. As she descends closer and closer to insanity, it takes less and less effort to remove the mask and reveal a different version of Blanche. Several times someone pushes her to the point where she's almost completely lost her mind, and she becomes hunched-over, disoriented, and withdrawn. And then of course at the end (spoiler alert) there's the Blanche with essentially no sense of reality, who is similar to flirtatious fake-happy Blanche with one important difference: it's no longer a conscious mask. I don't even know how to describe the difference; I only know that there is one. Somehow you can just tell earlier in the film that she's trying to be that way, and later in the film that she has actually become that way.

Those are the most common versions of Blanche, but there are others that come out briefly. One of my favorite parts of her performance is when her boyfriend is confronting her about the lies she's told him, and her voice suddenly gets much deeper as she spits out her defiant retorts. This really stood out to me because it's the only time her voice sounds like that, but instead of seeming out of place it works perfectly in that scene. There's no other scene like it in the movie, so of course she would only act like that then. I have to give some credit to the way the character is written, since it helps that it's such an interesting role, but I think there are very few people who could do the character of Blanche DuBois justice, and Vivien Leigh is unquestionably one of them. She was an incredibly talented actress, as her previous Oscar-winning performance demonstrated, and she also struggled with mental illness, as she suffered from what we would now call bipolar disorder. Those two criteria made her essentially perfect for the role, although it took a talented makeup department in addition to further acting talents for such a gorgeous human being to convince audiences that she actually had any reason to be insecure about her appearance.

A Streetcar Named Desire was the first movie to win three acting Academy Awards, a record that has only been tied once, by 1976's Network. Karl Malden won Best Supporting Actor and Kim Hunter won Best Supporting Actress. Marlon Brando was nominated for Best Actor, but he lost to Humphrey Bogart for The African Queen. Personally I thought Brando's performance was deserving of an award, but Bogart was also incredibly good, and his character was much nicer than the jerkface in this movie, so I think the Academy made the right choice. Malden's and Hunter's performances were also good, but I wouldn't have been surprised if they hadn't won, whereas I would have been shocked if Leigh hadn't won for her performance. I think her performance in Gone with the Wind was slightly more impressive than this one, but mostly just because that movie was twice as long.

Vivien Leigh was nominated for two Oscars, and she won both of them. Unusually, they're for her two most famous performances, which are also two of the best performances ever captured on screen. Sadly, due to a combination of factors, she wasn't in very many other movies. Some of that was because she was acting on the stage instead, but the rest was because poor health and a tumultuous personal life made it difficult for her to work. She died of tuberculosis in 1967 at the age of 53 after appearing in only 19 films, thus depriving the world of more fabulous performances like these two.

Next up: Shirley Booth, in a much less famous performance

1950: Judy Holliday for Born Yesterday

In a role she originated on Broadway, Holliday plays Billie Dawn, a mobster's girlfriend who has been called stupid so often that she just accepts it as fact. That is, until a reporter gives her some basic education, which makes her realize that she wants and deserves more out of life than she's been getting.

I think this is probably one of the most surprising wins so far. Given that Gloria Swanson's iconic performance as Norma Desmond in Sunset Boulevard was nominated alongside two from Best Picture Winner All About Eve - Anne Baxter as the cunning title villain and the legendary Bette Davis, who had already won Best Actress for two decidedly inferior performances - it now seems odd that a relative newcomer to Hollywood beat them for a performance that has been mostly forgotten. Furthermore, the Academy generally favors drama over comedy, which makes this an even more unlikely win. But just because it was unlikely doesn't mean it was undeserving. Judy Holliday's performance in this movie is at once hilarious and heartbreaking. A lot of people speculate that Davis and Baxter split the All About Eve vote, thus handing Holliday the Oscar, but while that may be partially true, I think Holliday deserves a lot more credit than she gets for this performance.

For one thing, her comedic timing was impeccable, and she demonstrates it perfectly in this role. I could not stop laughing at the scene when the Congressman and his wife are visiting, and she keeps carrying the radio around and starting to sing along with it in the worst possible place at the worst possible time. Also I think she and Broderick Crawford could have made an entire movie in which they did nothing but play gin rummy and it would have been one of the greatest comedies ever. But Billie Dawn is more than just a silly, dumb blonde, and Holliday makes her seem like a real person that the audience can sympathize with even before the reporter starts tutoring her. She definitely had the talent of producing facial expressions that are clear without being exaggerated. She especially had the confused-but-trying-to-appear-otherwise look down, which was particularly useful at the beginning of the movie. Once the reporter invites her to ask questions, she gradually drops that look and replaces it with one of eagerness for understanding. One of my favorite things about the way she plays this is that the transformation from clueless to clued-in is actually not incredibly drastic - she's basically the same except more assertive and using a wider vocabulary - indicating that Billie was always smarter than people thought she was. The only thing I don't like is that her voice is kind of annoying, but even that works to the performance's advantage here. All in all, this is a beautiful, comedic performance, and definitely deserving of recognition.

Unfortunately, Holliday played this character so well that she was essentially typecast for the rest of her career. Fortunately, this did work to her advantage in one respect. When she was called before the House Un-American Activities Committee, she played dumb so convincingly that she was neither blacklisted nor compelled to name names, which was extremely rare. But even being called before the committee probably negatively impacted her career. Add that to the fact that she was mostly just cast as less interesting versions of Billie Dawn and it's not exactly shocking that this was her only Oscar nomination. She only made a total of 13 movies, and in many of those she just had uncredited bit parts. It's kind of tragic that she didn't get to play more interesting roles on screen, especially because by all accounts she was actually incredibly intelligent. While it wouldn't be inaccurate to say that Hollywood screwed her over, it's not entirely their fault; they ran out of time. She died of cancer in 1965, just two weeks before her 44th birthday, which means she holds the morbid distinction of being the youngest Best Actress Winner to pass away. While I'm still hesitant to agree that hers was the best performance by an actress in a leading role in 1950, it was certainly one of the best.  And it's not like Bette Davis really needed another Oscar anyway.

Next up: the return of Vivien Leigh!

1949: Olivia de Havilland for The Heiress

In her second and final Best Actress winning role, Olivia de Havilland plays Catherine Sloper, the timid, awkward daughter of a wealthy but cruel father. She does all she can to please him until a handsome young man who is actually nice to her comes into the picture. Her father disapproves of him because he is poor and thus is probably a fortune-hunter, but Catherine loves him because of his kindness and charm.

Wow, this movie is amazing, and de Havilland's performance extraordinary. I thought she was fabulous in To Each His Own, but she is utter perfection in The Heiress. Catherine's journey from insecure to lovestruck to bitter is beautifully portrayed by her every movement, every glance, every line. For several of the better performances I've analyzed so far, I've mentioned the character's gradual transformation and how difficult it must have been for the actress to portray it so well. Catherine goes through several transformations, but they seem to happen suddenly. There are three very important turning points in the story, and each changes her completely. One might think that this would have been easier than showing a slow and steady journey; it's just like playing four different roles. But the way de Havilland plays it, at least, I have no doubt that each version of Catherine is always inside her; circumstances determine which part comes out, but she's always the same person. That can't have been easy to portray, and she does it brilliantly.

Apparently her co-stars, Montgomery Clift and Ralph Richardson, didn't think de Havilland was a very good actress. While I think they were decidedly wrong, I also think it might have helped her performance, at least in the first portion of the film when she's playing an under-appreciated character. Not that I want to take any of the credit away from her. This is undeniably one of the best performances I've blogged about so far. There have been so many good performances, but rarely do I feel for a character as much as I felt for Catherine. And that's saying a lot, since I often get very emotionally attached to movie characters. Her performance spoke to me and moved me, especially as a socially awkward introvert who can only imagine how horrible that would be without any sort of support system. I've been wanting to watch this movie for a while but never got around to it before now, so I'm very glad that this project finally gave me an excuse.

I hope Olivia de Havilland had a good 99th birthday today. This was her fifth and final Oscar nomination, although she continued making films and television through the 1980s. Watching her two winning performances for the first time has given me a much deeper appreciation for her acting talents than I had before undertaking this project. She was a truly remarkable performer, and it's comforting to know that she's still with us.

I'm leaving on vacation soon, so it will be at least two weeks before I watch another one of these. I hope all two of you who are reading this won't miss me too much. When I get back, I'll enter into the 1950s with Judy Holliday.