The country singer and songwriter, who died on Saturday at 88, tucked enduring aphorisms into tales about facing up to loss.

Kris Kristofferson was a generational singer-songwriter whose craftsmanship made country music feel broader and deeper.

A look back at some of the biggest and best songs by Kris Kristofferson, who has died aged 88.

“Freedom’s just another word for nothing left to lose,” Joplin sang in her signature blues-rock yowl — perhaps the best-known piece of wisdom in Kristofferson’s very wise catalog. “Me and Bobby McGee” topped the Hot 100 in March 1971, less than six months after Joplin’s death at age 27.

Kris Kristofferson claims four top 40 albums on iTunes and several hit songs as fans show their love for the country music legend, who passed away a few days ago.

Kris Kristofferson, an Oxford-educated Rhodes Scholar and Army veteran who wrote hit songs for Janis Joplin and Johnny Cash before starring in Hollywood movies, died Saturday at his home in Maui, a family spokesperson said Sunday evening. He was 88 and no cause of death was offered.

Kris Kristofferson, who died over the weekend at 88, was one of country music's greatest poets. His work elevated the genre and set a new standard for lyricism on Music Row. The big picture: Kristofferson's sprawling legacy includes well-known work as a singer and an actor.

Kris Kristofferson wrote some of the best songs in country music history. Here are five songs made famous by other artists.

Kris Kristofferson, a legendary figure in the world of country music, has also made a significant mark in the film industry. His unique blend of rugged charm and soulful performances has captivated audiences for decades.