Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson — the Highwaymen — rode into Albany’s Knickerbocker Arena touring behind their 1990 album Highwayman 2. The setlists were built around signature hits like “Highwayman,” “Desperados Waiting for a Train,” and “Silver Stallion,” plus each legend’s own catalog. Four living icons sharing one stage — there would never be another supergroup like this in country music.