Twenty Years of Oscar: Actress in a Leading Role

The next phase in my "Twenty Years of Oscar" retrospective, in which I travel back through the years since 1994, my first year with the Academy Awards, is Best Actress in a Leading Role. It's a category I've become quite familiar with in the six months. Back in August, I was asked by Andrew at A Fistful of Films to join a crew of movie bloggers on a quest to determine just who of the double Best Actress winners truly deserved, who had the best duo of roles. It was called "Twice a Best Actress," and I urge you to check it out if you haven't already.

Anyway, only one of these ladies has won twice (Hilary Swank), and, man, did she deserve both. And all of these other ladies had one big win for performances that were, to me, the most truly outstanding "Oscar roles" of the past twenty years.

Here are my favorite Best Actress Winners since 1994:

5. Charlize Theron as Aileen Wuornos in "Monster" (2003)

I actually never saw "Monster" until a couple years after Charlize Theron won the big prize. It's a decent movie, really intense. It is truly a transformative role. I mean, she's stunningly beautiful, and she pulled off butch, scary killer woman with such seeming ease. It's an unbelievable role that was a sure-fire win from the get go, especially in a pretty week field of nominees that year.

4. Helen Hunt as Carol Connelly in "As Good As it Gets" (1997)

Where Theron seriously transformed herself to win her Oscar, Helen Hunt won on pure charm. As a single mother and Jack Nicholson's favorite waitress in James L. Brooks' "As Good as it Gets," she just made audiences fall in love with her. I certainly did, and I love this movie. She matched Nicholson's mania to absolute perfection and, honestly, stole the show at times with some of the best lines in the movie.

3. Hilary Swank as Brandon Teena in "Boys Don't Cry" (1999) and as Maggie Fitzgerald in "Million Dollar Baby" (2004)

Here, I will redirect you to my write-ups on both of these roles for "Twice a Best Actress," done late last year. Swank, an actress nobody ever expected to win two leading role Oscars, did so and did so with pure grit and power.

2. Jennifer Lawrence Tiffany Maxwell in "Silver Linings Playbook" (2012)

I'm sorry, but I love Jennifer Lawrence. When she won the Oscar for Best Actress for "Silver Linings Playbook," my favorite movie of 2012, I felt like I won. Plus, she's just so real. I mean, she actually seemed truly shocked to win. She even tripped on her way up the stairs to the stage. I love her role in this movie, and, while many feel that "Silver Linings Playbook" was a weak portrayal of mental illness, I have to say this: I have lived with manic people my entire life, and this movie nails it. I have known these people my whole life, and I love this Oscar win.

1. France McDormand as Chief Marge Gunderson in "Fargo" (1996)

All actresses should be as lucky as Frances McDormand was when she got to star in Joel and Ethan Coen's true masterpiece, "Fargo." Well, she was married to Joel Coen, so I can't imagine it was much of an audition process. Chief Marge Gunderson is one of the great leading female roles not just in the last twenty years but of all-time. Marge is a pregnant, small-town Minnesota police chief in the midst of an unprecedented crime spree. The accent alone was worth an Oscar, but then she carried the entire emotional weight of the movie on her shoulders and totally sealed the deal. "You betcha!"