Let me help you, computer DJ

I look forward to the day when machine learning can differentiate between “don’t play this song because it is awful” from “ don’t play this song because I’ve heard this it a thousand times” (e.g. “Superfreak”, “Rapper’s Delight”, “Come as you are”). Related, I’d love a way to tell the machine learning “if you are ever stumped about what to play next, it’s always OK to slip this song in” (e.g. “Wouldn’t it be nice”, “Summertime Blues”, “Izzo (H.O.V.A)”, “Overture to Samson and Delilah”).