The last time I had flying lessons, I hit some building in Manhattan. Then my Uncle got shot in 2008. Darn...
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Explanation
Explain Bear
Alright listen up, you dummy. This joke is dark because the person in the joke is casually talking about crashing into a building in Manhattan, which is a clear reference to 9/11. Then they casually mention their uncle getting shot in 2008. You probably don't remember 2008 because your mama was still feeding you mashed peas, but there was a financial crisis. What a loser.