Watch The Highwaymen make their Farm Aid debut in 1992 with their signature hit "Highwayman" without Johnny Cash.

No friendship is always sunshine and rainbows, and a friendship where you work together will likely hit a few more bumps along the road. No group knew how to hash it out and still hug each other after ...

Hear songs from Willie Nelson, Waylon Jennings, Kris Kristofferson, Johnny Cash and more, inspired by a new book.

In 1990, Kris Kristofferson and The Highwaymen performed their hit song "Highwayman" during a sold-out concert in New York.

Kristofferson leaned into the outlaw identity in the 1970s, and in the process, helped Willie Nelson build Austin as an ...

Kris Kristofferson, actor, musician and long-haired activist who embodied the countercultural spirit of postwar America, died ...

Kris Kristofferson, a groundbreaking country music singer-songwriter and a Hollywood actor in 'A Star Is Born' and 'Blade,' ...

Tributes have been paid to Kris Kristofferson, the award-winning country singer and actor following his death at the age of ...

But the version that made it to #1 in America came from the Highwaymen, and not the outlaw-country supergroup of Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings. (That could ...

In 1985, he formed country supergroup “Highwaymen” with Cash, Jennings and Willie Nelson, which proved to be legendary. ©New Line Cinema/Courtesy Everett Collection Kristofferson played ...