Solution: "I Wish" rapper, 1995 - NYT Crossword

I was with you, everyone gnashing their teeth over a hip-hop natick, of all things, but then I popped this song into a search and realized that I love it. Twenty-five years ago, I had it burned onto a CD that I played all the time, but I forgot about SKEELO. This genre of rap, often earnest stuff with a lot of old jazz samples, is nostalgic and happy to me (and it’s fun to have the internet now, to identify and sync up those samples). The hint for that crossing entry, by the way, is Akron, and there’s another interesting city that comes up when you look into that artist.