Country Throwback: The Highwaymen Perform ‘It Is What It Is’ on ‘Late Show with David Letterman’ in 1995

by Katie Maloney

Watch country music legends, The Highwaymen, perform live on Late Show with David Letterman.

Pioneers of outlaw country music Waylon Jennings, Johnny Cash, Willie Nelson, and Kris Kristofferson teamed up as The Highwaymen in 1985. The group recorded three studio albums, Highwaymen, Highwaymen 2, and The Road Goes On Forever. Additionally, one of their first singles, “Highwayman,” soared to the number one spot on the charts in 1985. After the release of their third album, the group performed their song “It Is What It Is” on Late Show with David Letterman in 1995. Letterman announced the group as “The Mount Rushmore of country music.”

Kris Kristofferson Flew A Helicopter Into Johnny Cash’s Yard Before Joining The Highwaymen

Before Kris Kristofferson hit it big, he was working as a janitor in Johnny Cash’s recording studio. Kristofferson moved to Nashville to pursue his love for country music after being inspired by Cash. Kristofferson wanted to give Cash a song he had written but he knew he couldn’t just walk up and hand him a demo. So, he came up with a plan that only a true outlaw country musician would appreciate. Kris was a helicopter pilot, so he decided to rent a helicopter and fly it down into Johnny Cash’s front yard. Once he landed, he hand-delivered the song to Cash.

During an interview, Johnny Cash’s son, John Carter Cash, talked about Kristofferson’s plan. He said that many people think that Kristofferson delivered “Sunday Morning Coming Down,” one of Kristofferson’s most popular songs. But Johnny Cash’s son says that’s not the case.

“Kris says that it was another song. In fact, Kris says it was a song that wasn’t any good,” said John Carter Cash with a laugh. “But he had the will and the guts to land a helicopter in Johnny Cash’s yard which eventually led my father to record a Kris Kristofferson song. And then after years to come, he recorded many many Kris Kristofferson songs.”

Not only did Johnny Cash end up recording many of Kris Kristofferson’s songs, but he also formed The Highwaymen along with him in 1985. Note to anyone who wants to join the ranks of legendary outlaw country musicians: rent a helicopter.