Question: Which American singer-songwriter who collaborated with Shel Silverstein had a number one single in 1985?
Sentence (from "The Highwaymen (country supergroup)"): The Highwaymen was a country music supergroup composed of four of the genre's biggest artists well known for their pioneering influence on the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson.
Relevant evidence: Yes