The 25 Best Kris Kristofferson Songs, from Sunday Mornin' Comin' Down to Why Me

What is Kris Kristofferson's most famous song?

"Me and Bobby McGee" is Kris Kristofferson's most famous song, made a number one by Janis Joplin in 1971. "Sunday Mornin' Comin' Down", "Help Me Make It Through the Night" and "For the Good Times" are his other classics, and "Why Me" was his biggest hit as a singer.

Kris Kristofferson songs made famous by other artists

1. "Jody and the Kid", 1968: his first hit as a writer, for Roy Drusky.
2. "Me and Bobby McGee", 1969: first recorded by Roger Miller, then a number one for Janis Joplin.
3. "For the Good Times", 1970: a lush country classic for Ray Price.
4. "Sunday Mornin' Comin' Down", 1970: a number one for Johnny Cash and CMA Song of the Year.
5. "Help Me Make It Through the Night", 1971: a crossover smash for Sammi Smith.
6. "Nobody Wins", 1973: a heartbreak hit for Brenda Lee.
7. "Once More with Feeling", 1970: recorded by Jerry Lee Lewis.

Kris Kristofferson's own recordings

8. "To Beat the Devil", 1970: a song about staying true to your art.
9. "Casey's Last Ride", 1970: a melancholy story song.
10. "Darby's Castle", 1970: a haunting ballad from his debut.
11. "Just the Other Side of Nowhere", 1970: a homesick song about leaving.
12. "Loving Her Was Easier (Than Anything I'll Ever Do Again)", 1971: a tender love song.
13. "The Pilgrim, Chapter 33", 1971: a portrait of a restless songwriter.
14. "The Silver Tongued Devil and I", 1971: the title track of his second album.
15. "Jesus Was a Capricorn", 1972: a wry, warm title track.
16. "Why Me", 1973: a gospel-tinged number one country hit.
17. "Here Comes That Rainbow Again", 1981: a quiet song inspired by The Grapes of Wrath.
18. "Feeling Mortal", 2013: a late-career reflection on aging.

Duets and The Highwaymen

19. "From the Bottle to the Bottom", with Rita Coolidge, 1973: a Grammy-winning duet.
20. "Lover Please", with Rita Coolidge, 1975: their second Grammy-winning duet.
21. "Watch Closely Now", 1976: a song from A Star Is Born, opposite Barbra Streisand.
22. "Highwayman", The Highwaymen, 1985: a number one with Johnny Cash, Waylon Jennings and Willie Nelson.
23. "Desperados Waiting for a Train", The Highwaymen, 1985: a Guy Clark song they made their own.
24. "Silver Stallion", The Highwaymen, 1990: a song of freedom and the open road.
25. "A Moment of Forever", 1995: a gentle, reflective love song.

Who was Kris Kristofferson?

Kris Kristofferson was born in 1936 in Brownsville, Texas. He was a Golden Gloves boxer and a Rhodes Scholar at Oxford, then became a U.S. Army captain and helicopter pilot. He turned down a teaching job at West Point to move to Nashville, where he swept floors at Columbia's studios while trying to sell his songs. Once his songs became hits for other singers, he launched his own career as a singer and as an actor, starring in A Star Is Born, Convoy, Lone Star and the Blade films. He was inducted into the Country Music Hall of Fame in 2004 and died in 2024.

Why his songs changed country music

Kristofferson brought a poet's eye and frank, grown-up emotion to Nashville at a time when country songs rarely spoke so openly about loneliness, desire and regret. Songs like "Help Me Make It Through the Night" and "Sunday Mornin' Comin' Down" felt daring on country radio, and his success helped open the door for the singer-songwriters and outlaw country artists of the 1970s.

The story behind Me and Bobby McGee

Producer Fred Foster suggested the title, inspired by a secretary in his building named Bobbie McKee, and Kristofferson wrote the song about two drifters on the road. Roger Miller recorded it first, but Janis Joplin's version, released after her death in 1971, went to number one and made it a rock classic.

The helicopter and Johnny Cash

One of country music's favorite stories says that Kristofferson, then flying helicopters for the National Guard, landed one in Johnny Cash's yard to hand him a tape of his songs. Kristofferson later said the tale grew in the retelling, but he did land at Cash's home, and Cash soon recorded "Sunday Mornin' Comin' Down", which won the CMA's Song of the Year in 1970.

Kris Kristofferson songs for a memorial

"Why Me", "For the Good Times" and "A Moment of Forever" are often chosen for a celebration of life, especially for someone who loved classic country. See our memorial service songs for more.

More outlaw country

For more from the singers who made Kristofferson's songs famous and rode with him in The Highwaymen, see our Waylon Jennings songs and Conway Twitty songs, and for slow Sunday listening, our songs about Sundays.

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