Masterpiece!!! Similar movies?

It reminds me a bit Atom Egoyan's movies but since it's 20 years ago maybe i'm wrong. But he likes asymmetric relationships, etc.

Other great films that somewhat gave me similar vibes: Mystic River, History of Violence, the Pledge, the Ice Storm, Place Beyond the Pines, Drive, Amores Perros, Michael Clayton to name a few

A slightly jokey response, but isn't it a harsher version of "American Graffiti".
Parallels are: last night of freedom, all together, close friendships since school, much soul-searching going on.
No inadvertent insult intended here, but even the adopted dog has echoes of the girl Debbie who Terry "Toad" Fields picks up. She is way out of his league, but grows to like him; a bit like how the dog stops biting it's new owner!
I don't want to insult Edward Norton on a terrific film. There is no plagsrism here; just quirky co-incidences. Probably true of all thoughtful films on "life".

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Recently?

The Drop.

Hmm .. maybe "Up in the Air" with George Clooney? There is a similar reflection about whether the main character took the correct road in life.