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

He was known for classics like “Sunday Mornin’ Comin’ Down,” and for starring in films like “A Star Is Born" with Barbra Streisand.

8) Loving Her Was Easier (Than Anything I'll Ever Do Again) - One of his most romantic songs and Kristofferson's first chart hit, in 1971. He later re-recorded it with The Highwaymen, a supergroup of outlaw country artists that also featured Cash, Jennings and Nelson.