Being Fired for not Supporting Mr. Burns' Plan of Stealing Oil and Blocking off the Sun - Who Shot Mr. Burns
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CuriousUserX90
4 years ago Report
All to the Extent that made him a Hideous Drunken Wreck.
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Top 10 Worst Things to've Happened to Mr. Smithers in The Simpsons
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CuriousUserX90
Forced to do the Mount Useful Challenge Alone - Mountain of Death
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#3
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CuriousUserX90
Having been Lied to about his Father's Death - His Whole Life prior to Season 13
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CuriousUserX90
4 years ago Report
Waylon Smithers Sr. died when attempting to stop a Crisis at the Nuclear Power Plant when his son was just a baby, luckily Mr. Burns had good sympathy about his death, unable to tell the truth to his Future Assistant.
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#4
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CuriousUserX90
Being Whipped in the Springfield Marathon - New Kids on the Blecch
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#5
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Whenever Mr. Burns Humilates himself or Whenever Mr. Burns does Something else that's Humiliating - Various Episodes
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#6
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CuriousUserX90
Having Thought Mr. Burns to've Died - The Episode where Nr. Burns went through Amnesia