Why The Highwaymen Didn't Request Any Alcohol on Their Tour RiderWhy The Highwaymen Didn't Request Any Alcohol on Their Tour RiderWillie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson were some of the best-known outlaws in country music history, so why were they drinking 7-Up backstage?Carena LiptakCarena Liptak
30 Most Bone-Chilling Country Songs About Death, Ranked30 Most Bone-Chilling Country Songs About Death, RankedCountry music is all about being honest and real — and death is as real and raw as it gets. Carena LiptakCarena LiptakSterling WhitakerSterling Whitaker
Country Music Memories: Four Country Icons Record 'Highwayman'Country Music Memories: Four Country Icons Record 'Highwayman'Talk about an anniversary to remember!The Boot StaffThe Boot Staff
Country Music Memories: 'Highwayman' Hits No. 1 on BillboardCountry Music Memories: 'Highwayman' Hits No. 1 on BillboardOn Aug. 17, 1985, the Highwaymen hit No. 1 with their debut single, "Highwayman."Gayle ThompsonGayle Thompson
Country Music Memories: The Highwaymen Begin Tour in HoustonCountry Music Memories: The Highwaymen Begin Tour in HoustonOn March 3, 1990, the country supergroup kicked off their concert tour at the Houston Livestock Show and Rodeo.The Boot StaffThe Boot Staff
'Highwayman' Album Certified Gold — Country Music Memories'Highwayman' Album Certified Gold — Country Music MemoriesIt was the country music supergroup's first album.Gayle ThompsonGayle Thompson
Top 10 Country Songs About CowboysTop 10 Country Songs About CowboysYee-haw!Annie ZaleskiAnnie Zaleski
Top 10 Country Grammy Awards MomentsTop 10 Country Grammy Awards MomentsRemember when ...?Christina VinsonChristina Vinson
50 Country Albums Everyone Must Hear Before They Die50 Country Albums Everyone Must Hear Before They DieWhether you're a country fan or not, these albums are must-listens!The Boot StaffThe Boot Staff
2019's Top 10 Country and Americana Collaborations2019's Top 10 Country and Americana CollaborationsThe Boot counts down the most unforgettable team-ups of 2019.Carena LiptakCarena Liptak