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Breaking $1/gallon on gas
I remember when it happened here some gas stations didnt have enough display panels to fit the new digit, so they'd paint or sticker an awkward "1" in front. I thought it was funny, like they had never planned for it to reach that many digits (ever?)
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Breaking $1/gallon on gas made an impression on me. Also the dot com bubble. That was probably the last time I remember mainstream discussion of inflation. I also remember discussion about deficits in the late '90s (although I don't remember why, Clinton balanced the budget if I recall).