I am in awe of how random and wrong this was:

J: Alexa, play the song “I spent my last ten dollars on birth control and beer”.

A: Here’s Rake and Ramblin’ Man, by Don Williams, on Amazon Music.

J: Alexa, play the song “I spent my last ten dollars” by “Two Nice Girls”.

A: I Spent My Last $10.00 (On Birth Control & Beer), by Two Nice Girls, on Amazon Music.

(to be clear, this was not mis-heard; the voice history in the app shows that every word was clearly understood, and she still ended up with a completely wrong song)

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