The entire fakeout ending to The 25th Hour, with Brian Cox telling Ed Norton to flee west, start a new life, and never attempt to come back lest he risk capture.

Crimes and Misdemeanors

In context, this is one of the most powerful exchanges I've ever seen between father and son, even though it's a daydream...

Judah: And if a man commits a crime... if he kills?
Father: Then one way or another he will be punished.
Uncle: IF he's caught, Sol.
Father: If he's not caught, that which originates from a black deed will blossom and follow a man.
Uncle: Well, you're relying a little too heavily on the bible, Sol.
Father: No no no, whether it's the Old Testament or Shakespear, murder will out.
Judah: Who said anything about murder?
Father: YOU did.
Judah: Did I?

http://www.youtube.com/watch?v=HSZP-vXiBqs

Little Miss Sunshine.

They are in the van after Richard finds out that he's not getting the big deal and his father slides up behind him and, hand on his shoulder, says
"Richard, whatever happens, you tried to do something on your own, which is more than most people ever do. I include myself in that category. You took a big chance, it took guts, and I'm proud of you."

I think part of what makes it so interesting is that it's so not like Grandpa's usual demeanor with the sex lecture and the cussing etc. Before he acted pissed off and put out. Here he's acting like a father again. for one brief moment.

And then pretty much the next scene he's dead.

Well gotta mention Big Fish, and the super sad ending.

Will Bloom: ...we see that everybody is already there. And I mean...everyone.
Will Bloom: Unbelievable.
Senior Ed Bloom: The story of my life.
Will Bloom: The strange thing is, there's not a sad face to be found. Everyone is just so glad
to see you...and send you off right.
...
Will Bloom: You become what you always were. A very big fish. And that's how it happens.
Senior Ed Bloom: Yeah. Exactly.

http://www.youtube.com/watch?v=d3lE_c3gMto