35 Years Ago: ‘Highwayman’ Album Certified GoldIt was the country music supergroup's first album.Gayle Thompson
36 Years Ago: Waylon Jennings, Willie Nelson, Johnny Cash and Kris Kristofferson Record ‘H…Talk about an anniversary to remember!The Boot Staff
35 Years Ago: ‘Highwayman’ Hits No. 1 on BillboardOn Aug. 17, 1985, the Highwaymen hit No. 1 with their debut single, "Highwayman."Gayle Thompson
31 Years Ago: The Highwaymen Kick Off Concert Tour in HoustonOn March 3, 1990, the country supergroup kicked off their concert tour at the Houston Livestock Show and Rodeo.The Boot Staff
2019’s Top 10 Country and Americana CollaborationsThe Boot counts down the most unforgettable team-ups of 2019.Carena Liptak