That isn't the point though. The radio stations play what attracts the largest crowd. If playing Woody Guthrie would garner more listens than Elvis, the beatles, etc. they would be playing Woody Guthrie.
Even if you want to just look at Spotify. Who has more plays from rappers in the 2000s? 50, Eminem, Jay, Nas, etc. Or MC Lyte and krs 1? Not only that, but the most popular KRS songs are not his socially relevant commentaries, but his most popular songs. If your theory was correct, The Truth By KRS would have more listens than Candy Shop by 50 cent, but it doesn't.
I do agree with your other point. Songs that were popular, but didn't age well. Like Ron Browz for instance. Is not going to be played on the 2000s channels 50 years from now, but Drake was not some one hit wonder. Drake was the most popular rapper for the entire decade. If you think he is just going to fade away, you are crazy. People thought frank sinatra was just some random pop star that would fade away and was aimed towards teenagers and that no one would bump him as an adult. Now we have 95 year olds dancing to him.
Historically. The musicians that are listened to 30-40-50 years later are the ones who were the most popular in their prime. Look at the most popular musicians from any decade and 9/10 times they have the most listens on spotify, when compared to their contemporaries.
Now if we are talking hundreds of years later. Like Mozart and Beethoven. Then you need to either create a genre or have done something to really push forward a genre. There were plenty of musicians more successful than Mozart when he was alive, but people remember Mozart because he did more than any of the more successful musicians, of his time towards advancing his genre.