This film shows what a great script and amazing actors can pull off. Penn does an amazing job pulling everything together to project a general feeling of despair. Few films send such a powerful emotion.
David Morse, who I believe makes every movie his is in (Green Mile, Contact, Hearts in Atlantis) much better, puts in an amazing performance as someone whose guilt is unshakable.
Jack of course is a living legend, but this is a performance that really transcends the typical greatness we have come to expect. He really makes you feel a piece of the powerful grief he lives with, and somehow makes you laugh.
Angelica Houston is just about the only actress I have seen steal a scene from someone like Nicholson with such subtlety. One of my favorite scenes is Nicholson and Houston in the dinner. At the conclusion, you can almost feel the door slam on their relationship.
And Robin Wright Penn gives the best performance of her career. Obviously the man and wife relationship helped Penn know how to best play her strengths. The scene when Morse confesses his worst secrets to Wright is amazing. She has few lines, but really shows volumes in her reaction.
I recently watched The Woodsman and felt that Sedgwick also did an amazing job in the same type of scene, but yet went in a completely different direction.
This film is often compared to The Pledge, and rightfully so. In my opinion though, The Crossing Guard is by far a better film. The fact that Penn had to wait until Mystic River to get his Oscar credit is a shame. This movie was overlooked.