Are we talking about only 1 time certain singers or groups hit the top 40 charts? Charlie Daniels had quite a few hits but he’s a country singer, isn’t he? So many of his populsr songs apparently didn’t cross over.
Also Harry Chapin had a number of albums, but limited success if we define this based on hot 100 or top 40 charts.
Chapin had Taxi, and Cats In the Cradle