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 nuanced craftsmanship made country music feel broader and deeper.

“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.

After years as a struggling songwriter, he found his voice with a direct, evocative style that launched his decades-long career as a musician, actor and activist.

We look at nearly a dozen No. 1 hits the late Kris Kristofferson earned during his career, as a songwriter and/or artist.

Kris Kristofferson, a Rhodes scholar with a deft writing style and rough charisma who became a country music superstar and A-list Hollywood actor, has died.