8. The Highwaymen
Key Members: Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson
Signature Songs: "Highwayman," "Desperados Waiting for a Train" and "Silver Stallion"
Current Status: They haven't recorded anything since 1995's The Road Goes on Forever, and since then both Cash and Jennings have passed away. Kristofferson is in much better shape than he was a few years ago since learning he was suffering from Lyme Disease and not Alzheimer's, but it still seems like the Highwaymen's road has come to an end.