Which American singer-songwriter who collaborated with Shel Silverstein had a number one single in 1985?
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. Kris Kristofferson:  Kristofferson composed his own songs and collaborated with Nashville songwriters such as Shel Silverstein.
i don't know