Well I had this nice long post written... and then the power went out and it was all deleted. Well here are the main points anyways.

Matt Damon is a shoe-in to win at least one award this year. He's a likely double nominee (Best Actor for The Good Shepard and Best Supporting Actor for The Departed), he seems well liked and respected in Hollywood, he has been nominated before and was the Oscar golden boy in 97/98 for Good Will Hunting.

The only thing that could possibly screw him up is the vote splitting between the 2 categories and possibly Jack Nicholson out-shining him in The Departed. But I still believe he will win for The Good Shepard. Any thoughts?

I HIGHLY doubt either nomination will happen. Departed you got DiCaprio and Jack Nicholson will will most likely be more of the main roles in the film, so if anything i'd say Jack Nicholson would be nominated for best actor while DiCaprio gets a nod for best supporting. I have no idea about Sheperd, but I think it'll be the Syriana of this year, so I doubt he'll pull a best actor.

If he does get a nomination for best actor for Sheperd I give him a 0% chance of actually winning, it doesnt seem that interesting.

dparted is dicaprio best actor and nicholson or wahlberg(what?!) for supporting.

Yeah I gotta agree with Kill, it's the Leo and Jack show in terms of acting awards for The Departed.

Leo would seem to have an even better chance with December's Blood Diamond.

If they follow the original (which according to all I saw thus far they are doing) there is no way Nicholson is getting a lead nom and DiCaprio supporting. Both might be going for lead, but no way is DiCaprio's character supporting.

Yes, I'd have Leo as lead and Jack as the token supporting baddie.

I was just ABOUT to say that, but then realized where Kill was coming from.

Gangs of New York. Daniel Day Lewis had a (somewhat) similar role there and to me he was supporting, but got a Best Actor nod. That's why I didn't argue that. But DiCaprio is definitely 100% lead here.

Jack's characters seems much more interesting and even with less screen time i'd say he has a better chance at best actor then Leo, unless early world about his character being a bit too over the top is correct.

He wont get it

Over the top hasn't stopped the Acamdey from nominating.

Have you seen the original? If anything, both are leads, though in reality, Nicholson's character is distnictly supporting. DiCaprio's character is also much more complex and conflicted.

He'll win an acting one eventually, I think.

Havnt seen it and probably wont until I see this one, I dont want it to take away from this film. I think if either actor is nominated for supporting they're almost a locked for an oscar, unless the movie is just plain bad, just for the fact that like you said that both roles are basically lead, DiCaprio is kinda owed one and well Nicholson is Nicholson. Unless another supporting role such as maybe Bale in Prestige totally blows people away, which I wont be shocked if that happens either.

Eh, I don't know about Nicholson. It depends on competition. Even if he is really really brilliant in it and all...he has THREE Oscars already which is more than a luxury.

BTW I dont think Damon will ever win an oscar, atleast not best actor. He's a fine actor, almost is always good, but he never really made me just say " Whoa ", I dont think he'll ever reach a level of true greatness I do think he'll always be a damn fine solid actor though. To me it just doesnt seem he has the depth to be truely GREAT.

Some actors as big as him can get away with it.

If Damon gets a nomination I think it's likely to come from The Good Shepherd. He didn't look that great in the trailer for The Departed IMHO. However, if The Good Shepherd is an Oscar blockbuster, he could get good will from The Departed. The Bourne series and Oceans 11 and 12 have really helped his career, even when he does something like The Brothers Grimm. He's building a solid career and has a reputation for being very easy to work with. All of those add up to an Oscar win someday. Not yet, but someday.