YMMV / The Simpsons S 3 E 24 Brother Can You Spare Two Dimes

• Alternate Character Interpretation: An easy-to-miss detail is that Herb previously claimed to have worked his way through university scrubbing toilets. So he has experience in blue-collar work but is currently unemployed as a hobo. This could mean The Homer was such a disaster it rendered him unemployable in any field (which sounds harsh but Kirk van Houten would become unemployed for way less). Or it could mean he thinks he's above that work now. Or he'd rather spend all his time hating Homer...
• Broken Base: Exactly how sympathetic is Herb? Being reduced to living on the street is certainly extreme, but his lack of a safety net and refusal to admit fault are entirely his own doing.
• Unintentionally Sympathetic: We're expected to see Homer as a jerk and a pessimist who doesn't believe in Herb's idea despite owing him a chance to rebuild his fortune but Homer is also the one funding Herb's idea with money that he was given as compensation for the power plant turning him sterile. Not only that but Homer clearly does want to make amends with Herb because everyone (including himself) blames him for the actions of their last encounter despite the fault being more on Herb's choices, and Herb has been rude and violent towards Homer. Homer is actually being reasonably doubtful considering that he's the only one who would lose out if things didn't work for Herb.

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