Earlier quoted context omitted.
I always thought that hustler was synonymous with confidence artist or a low level scammer. That it’s now considered a positive word is fascinating to me.
Hustler is used a lot in rap. It's always been there. A hustler hustles. They put in work. They are in the grind. It's all about turning a nickel into a dime. In other words, they sell a lot of crack. Nothing deep. https://www.youtube.com/watch?v=xZbwTCrnktY - Cassidy - I'm a hustler https://www.youtube.com/watch?v=sv6CbP4kVno - Lil Wayne - Hustler Muzic
Technically I believe it often meant any odd job to make money whether legal, illegal or a grey area. So selling weed, shoveling a driveway, and busking where you could get kicked out at worst all count.