Right from the beginning, Jennings released a cover of Dylan’s From The Freewheelin’ Bob Dylan track “Don’t Think Twice, It’s All Right” on his debut album Waylon at JD’s.

Kris Kristofferson, Waylon Jennings, Johnny Cash, and Willie Nelson joined forces in 1985 to give country music their own powerhouse under the name The Highwaymen. “It came out of pure friendship,” ...

Johnny Cash’s Ring of Fire (The Best of Johnny Cash) headed the inaugural chart. The compilation was well-timed: “Ring of Fire” had headed Hot Country Songs for seven weeks the previous ...

This supergroup collaboration between Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson brought together four of country music’s greatest outlaws. The album’s blend of their ...

Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson perform live at Long Island's Nassau Coliseum in 1990.

Ol’ Waylon remains one of Jennings’ most successful releases. It topped the country albums chart for 13 weeks and became the first album by a solo country artist to reach Platinum status.

Two legends paying homage to one another – and having a little fun.

Post Malone and Ashley McBryde performed a tribute to Johnny Cash and June Carter Cash at the Grand Ole Opry's 100th anniversary celebration. Johnny Cash and June Carter Cash, a legendary country ...

The two singers paid tribute to Johnny Cash and his wife June Carter Cash in singing "Jackson," the couple's most famous duet. Video shared at the Opry's Instagram finds the two contemporary ...