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  • Alternative Character Interpretation: Is Jessie really the Cool Old Guy Adam thinks he is, or is he just an immoral old man and a Manipulative Bastard exploiting his grandson's familial man crush on him just for kicks and to annoy his son, Adam's father Vito? When Jessie finally asks Adam at the end "can you get out from under me?" is he finally acknowledging that he was a bad influence on Adam and encouraging him to be his own man, or is he once again just exploiting Adam's adoration of him?
  • Moment of Awesome: Vito punching Jessie.
  • Questionable Casting: Sean Connery and Dustin Hoffman as father and son. Everyone called the filmmakers out on this back in 1989 - not only is Connery older by a mere seven years but as People's review pointed out, "they don't look remotely alike, and they're about as close in size as a moose and a rabbit." (We won't get into how Matthew Broderick could possibly result from this lineage.)
  • Unintentionally Unsympathetic:
    • Assuming he's not meant to be an Unsympathetic Comedy Protagonist, Adam. His father, Vito, worked his ass off to give Adam a better life than Vito himself had, but Adam refuses to take advantage of the opportunities his upbringing provides and basically wants to throw his life away for a ridiculous burglary just because he thinks it'll be fun and despite everything his father does to keep him out of jail the ungrateful little brat complains that his father never respected him and complains about how lousy his upbringing was even as he and Jessie complain about his father complaining about how hard his own life was. And to top it all off Adam actually has the gall to claim that Jessie understood and respected him more than Vito ever did and even goes so far as to say Jessie was "fun" to be around, despite the fact that Jessie was by all accounts a terrible father who tried to turn both his son and grandson into criminals, spent more time in jail than he did at home, and Jessie seemingly had no real qualms with leaving Adam in jail for about 15-20 years despite how much Adam sucked up to him. And yet Vito is made to feel like he's the bad guy with a mountain of Informed Wrongness dropped on him.
    • Jessie as well, assuming he's also not meant to be seen as an Unsympathetic Comedy Protagonist. For all of Sean Connery's charismatic bluster there is simply no hiding the fact that Jessie is not a particularly nice or sympathetic man.

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