When Chicago won Best Picture in 2003, it was the only time that the Best Picture winner annoyed me. I though that ever other film nominated that year (including The Hours, Lord of the Rings: The Two Towers, and The Pianist) was more deserving of the win and I was personally rooting for this film.
This was of the first of the (so far) three collaborations between Martin Scorsese and Leonardo DiCaprio and I have to say that it is my favourite of the bunch (though The Departed comes a close second).
The film deals with gang warfare in the early days of New York City, which centered around Irish immigrants fighting against the so-called “Natives.” The story is fictional, though it contains some characters based on real individuals, such as Boss Tweed and Bill the Butcher (played wonderfully by Daniel Day-Lewis).
It probably wouldn’t be too much of a guess to say that the political climate at the time (the ceremony happened right at the start of the Iraq War) prevented a violent film like this to win at the Oscars, however in my book, this film was the best film of 2002.