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It's strange to think that the deeply unconventional, outspokenly feminist Katharine Hepburn made her Hollywood comeback with these two films. In The Philadelphia Story, Tracy is blamed for her ex-husband's drinking problem and her father's affair; apparently if she were less frigid, the men around her wouldn't be such losers. They spend the entire time telling her how she fails to live up to what a woman ought to be, and the crux of the film is that they're right! In Woman of the Year, Tess is a "career woman," and her marriage suffers as a result. Her inability to make breakfast for dear ol' Spencer Tracy is meant to belie her femininity. These are both difficult to watch for me today but at least there is a lot going on in The Philadelphia Story, and pages and pages of sparkling dialogue. Whatever else it is, it's a beautifully executed film, although I do think Jimmy Stewart's Oscar was mostly a consolation prize for Mr. Smith Goes to Washington, despite his fine work here. Woman of the Year is just a chore. It's slow and unpleasant and relentlessly sexist. I'll give this one to The Philadelphia Story, which I can enjoy on certain levels.
Woman of the Year works until it doesn't (the kitchen scene which ends it). The Philadelphia Story works all the way through.