One of the worst Best Picture nominees ever

Rating: Null/10 (6 July 2003)

This movie is a sad failure, as it's obvious how badly Scorsese wanted to tell a story about this time period and how much hard work he put into the details. But the movie ultimately fails because of a very thin story overwhelmed by artifice - and two unfortunate casting choices.
I think it was Scorsese who has said that the majority of a director's job lies in casting the right actors. If that is true, the movie is doomed by the choices of DiCaprio and Diaz in two of the lead roles.
I like Diaz and think she's a charming, effervescent, and sexy screen presence. But she has a very modern appearance, demeanor, and spirit, and she just does not work in this role.
As for DiCaprio, regardless of whatever acting talent he may possess, he cannot overcome his own physicality. DiCaprio has the face and body of a young teenage boy, and although he is getting close to 30 now, his appearance has not aged much since "What's Eating Gilbert Grape." He hasn't yet developed an adult man's beard growth and still has a chubby, cherubic face (with a whisker here and there above his lip and on his chin). And although his teenage fans are many, DiCaprio just can't convey true adult masculinity, virility, or sexual tension. His appearance works well in, say, "Catch Me If You Can," where the role is that of a teenager masquerading as an adult.
But in this movie, we are asked to accept him as a tough, vengeful, full-grown man who is able to murder Daniel Day-Lewis's legendary upperclass thug Bill the Butcher. It's so preposterous a notion that the actual act is obscured by smoke in the climactic scene (though we do see an aftermath shot of DiCaprio with a dirty face and scruffy red hair, looking much like Chucky from "Child's Play"). This is no fault of DiCaprio's, really - it's just a monumental act of miscasting. Just as a reasonable audience could not accept, say, DeNiro as an overweight black woman or Streep as a high school cheerleader, DiCaprio simply does not have the physical appearance to be convincing in this role.
Day-Lewis, however, is not miscast, and gives an amazing performance, although his modern-cliche-sounding Noo Yawk accent was at times distracting and over-the-top. Imagine how different this movie could have been with, say, Colin Farrel or Heath Ledger or Ewan McGregor paired with, perhaps, Kate Winslet or Helena Bonham-Carter.
But what bothered me most about this movie is that, even aside from the casting misfires, I was never able to suspend my disbelief. Everything about the movie seems artificial, even the sets and costumes; I assume they are authentic in appearance but seemed like something out of a Dickens PBS/BBC movie. This movie cost about $100 million, I've read, and the production values do look expensive. But they still didn't seem believable to me. I was always aware, perhaps becuase of the meagerness of the story being told, that I was watching footage shot on a elaborately-constructed Cinecitti backlot.
There wasn't a single frame of this movie in which I was not acutely aware that these were actors in costumes, on sets built in Italy, and that Scorsese was standing just off camera telling everyone exactly what they should do.
I suppose this is an interesting, neglected time period in history, and not a bad idea for a movie setting. Yet a setting is not enough - the movie needed a compelling story. All the work and money has gone into these background elements (expensive sets, costumes, actors, and special effects) without having anything very interesting in the story department. The movie would have been much more successful artistically if it had cheap costumes, shabby sets, unknown actors - but with an actual story that could hold our interest.