The problem with being in different generations is the music from one rarely passes completely to another, and the newer artists who come along aren't appreciated by those who didn't grow up with them. Someone truly wonderful is almost always lost along the way.
I've forced my children to listen to music from the '30s and '40s passed to me by my parents and my granddaughter has dragged me kicking and screaming to sometimes enjoying rap. There is no way they will appreciate all the artists I know simply because they have never heard of them outside of maybe one song on constant replay on some very oldies station such as KIXI. Nor will I ever like something containing previously forbidden four letter words no matter how socially relevant the other lyrics or the beat.
If you were born after 1980 when mentions by Harry Anderson on Night Court gave his career a new familiarity with youngsters born after the Beatles, let me introduce you to Mel Torme. He may have first gained fame as a WWII pretty boy singer mass produced to the world as the Velvet Fog. He became simply one of the best jazz singers ever, and to this day jazz afficianados adore him. Here is a small taste of a concert with George Shearing. Prowl around all the music on this You Tube link and your next stop may be everything available on Amazon.
Here is the wonderful Salon dot com obituary written for Mel Torme for later reading, but in the meantime, who do you really love that may end up forgotten unless you remind others they existed?
