For those who grew up with his music, his presence in our lives feels irreplaceable. Now, with Willie Nelson being the last surviving member of The Highwaymen, we’re reminded of an era that’s slipping away — an era that shaped American music and culture.

Kristofferson’s life, however, was far more than his time in the legendary country supergroup. With roots in Texas and Sweden, his career took off in the 1960s, and he penned timeless classics like ”Sunday Mornin’ Comin’ Down,” ”Help Me Make It Through the Night,” and ”For the Good Times.” His lyrics weren’t just songs — they were poetry that captured the human condition in all its raw beauty.

It would take most men a dozen lifetimes to accomplish what Kris managed in one. Not only was he an award-winning musician, but he also shone on the silver screen, starring alongside Barbra Streisand in A Star Is Born (1976), a role that earned him a Golden Globe.

And now, it’s his final photo that has left fans in tears.