I want to say Brokeback Mountain so they could, maybe, get the hint.
But, jokes aside, I have read a couple of books (some time back) that I think would work well for them (given that you want to know what kind of books I'd make them read to hit internal cords rather than books that I know they would simply enjoy reading):
For Dean: The Road by Cormac McCarthy.
The story follows a father and a son (both unnamed) travelling through the United States in a post-apocalyptic scenario. It is never really specified what initiated it all— some scenes hint at a nuclear conflict— but society has collapsed and the world is now in the hands of the little survivors left (most of which are either cannibals, marauders, thieves and more).
The mother of the kid committed suicide shortly after he was born as she had been pregnant when it had all started. The father carries the revolver she used— now with only two rounds— with the idea of using it as a last resort shall they fall in the hands of the canniblas.
Overall, the story is focused on the father-son relationship and their journey over several months as the father slowly dies from bronchitis and dies in his son's arms. The kid then gets 'adopted' by a man who decides to take him under his protection.
I feel like the focus on the father-son relationship and the apocalyptic feel to the story would resonate with (at least first seasons) Dean's mind.
For Sam: The Midnight Library by Matt Haig.
The story follows Nora Seed and focuses on her unhappiness regarding her life. She has a bad relationship with her brother, her best friend lives far away, she just got fired, she seemingly lost her music teaching gig and her cat just died.
She hates everything as it is and decides to end it all by committing suicide by overdose. But, instead of dying, she finds herself inside a limbo library— the Midnight Library— where each book is a retelling of her life's story had she made different choices. The only lifes that she can access are the ones that were possible outcomes of the one she just lived (hence the ones with slight variations that would've still turned into butterfly effects, but still wouldn't have differed much from her original one).
She lives through many different scenarios and possibilities, but she realizes that the boy whom she taught piano to— which helped shape him and give him a passion to focus on— has never had her as a teacher and is now in constant trouble with the police, and the neighbour she provided with medicine doesn't even know her. This makes her understand she doesn't feel ready to die and she ends up rewriting her story to survive the overdose, get to a hospital in time— with her neigbour's help—, makes up with her brother, and plans a meet up with her best friend.
In short, I feel like this story would hit Sam just right due to his constant feelings of guilt regarding stuff he had no contol over (like for Dean I'm talking more in the earlier seasons vibe) and his past trauma. He always looks like he wants to go back and fix things, supposing that if he never went to Stanford or if something else changed, they wouldn't end up where they are at the end.
I think this story would help him understand that, no matter how hard and ugly his life may seem to him, it's still his. He would still miss events that never happened somewhere else or people he's met through it, be it friends or foes like Castiel and Crowley.
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