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

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

Kris Kristofferson might have been too handsome for his own good, but he helped country music find a new path.

8) Loving Her Was Easier (Than Anything I'll Ever Do Again) - One of his most romantic songs and Kristofferson's first chart ...

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

There’s no better songwriter alive than Kris Kristofferson,” Willie Nelson, bandmate alongside Johnny Cash and Waylon ...

He was a songwriter, a singer and an actor, known to many Texans for his part in the "outlaw country" movement of the '70s ...

More than 50 years ago, Kris Kristofferson, a Rhodes scholar equally drawn to the words of William Blake and Hank Williams, ...

American country music superstar and Hollywood actor Kris Kristofferson has died aged 88 at his home on Maui, Hawaii, on ...

Kristofferson’s aforementioned second album, The Silver Tongued Devil And I, played something of a supporting role in ...

Country Music Hall of Fame-inducted Grand Ole Opry member "Whispering" Bill Anderson discusses the impact of Kris Kristofferson's artistic legacy.

Starting in the late 1960s, the Brownsville, Texas native wrote such country and rock ‘n’ roll standards as “Sunday Mornin' ...