Kris Kristofferson No. 1 Hits: History of His Chart-Topping Tracks

by Jacklyn Krol
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Kris Kristofferson is an artist and songwriting legend. Discover a list of his hit No. 1 songs and the stories behind them, below.

First Kris Kristofferson No. 1: “Why Me”

Kris Kristofferson has one single No. 1 hit as a solo artist and that is “Why Me.” He recorded the track with backing vocals from his wife Rita Coolidge and Larry Gatlin. The song was inspired by Gatlin’s track, “Help Me Lord,” along with his church.

“Is anybody feeling lost?” “Up goes my hand,” Kristofferson recalled to Wide Open Country of a mass. The minister asked him if he was willing to accept Christ into his life. “I’m kneeling there,” Kristofferson added, “and I carry a big load of guilt around…and I was just out of control, crying. It was a release. It really shook me up.”

The song is so relatable and well-loved that numerous artists like Elvis Presley, Johnny Cash, Conway Twitty, George Jones, Merle Haggard, Willie Nelson, Connie Smith, have all covered it.

  • Album: Jesus Was a Capricorn
  • Year: 1973
  • RIAA: Gold
  • Standout lyric: “Why me Lord, what have I ever done / To deserve even one / Of the pleasures I’ve known”

“Highwayman”

“Highwayman’ was the hit for the group of the same name, consisting of Kristofferson, Willie Nelson, Johnny Cash, and Waylon Jennings. Each member took a verse solo before joining in together on the chorus. Jimmy Web originally wrote the song in 1977 for his album, El Mirage. Glen Campbell also released his cover in 1979 for an album of the same name.

Ironically, Webb played the song for Jennings but it wasn’t till hearing Campbell’s version that he got it and realized how good it was.

The Highwaymen supergroup released their debut album of the same name. It went on to become a No. 1 and Platinum record.

  • Album: Various
  • Year: 1977, 1985
  • RIAA: Platinum
  • Standout lyric: “I was a highwayman / Along the coach roads I did ride / With sword and pistol by my side”
  • Awards:  Grammy Award for “Best Country Song”

“For The Good Times”

“For The Good Times” was written by Kristofferson and originally recorded by Bill Nash in 1968. Kristofferson later added his rendition to his 1970 debut album. Ray Price was the artist who made it a No. 1 hit with his rendition, which was his first No. 1 single in over eleven years.

Kristofferson wrote the song in 1968 after a road trip from Nashville to the Gulf of Mexico. After the song’s success, Al Green, Perry Como, among numerous other artists recorded covers of the song.

  • Album: Various
  • Year: 1968, 1970
  • RIAA: Platinum
  • Standout lyric: “Lay your head upon my pillow / Hold your warm and tender body / Close to mine / Hear the whisper of the rain drops”

“Please Don’t Tell Me How the Story Ends”

Ronnie Milsap recorded the song and it quickly became his second No. 1 single. He also won his first Grammy Award for his performance of the song. Ironically, the 1974 version was his second recording of the song. He first recorded it in 1971 for his debut self-titled album. The same year, Bobby Bare recorded the song for his record, Where Have All the Seasons Gone.

Finally, Kristofferson gave his own rendition of his lyrics with Coolidge for their duet record, Natural Act.

  • Album: Pure Love
  • Year: 1974
  • RIAA: Platinum
  • Standout lyric: “See the way our shadows come together / Softer than your fingers on my skin / Someday this may be all that we’ll remember of each other / Please don’t tell me how the story ends”
  • Awards: Grammy Award for Best Country Vocal Performance

“Sunday Mornin’ Comin’ Down”

Ray Stevens first recorded “Sunday Mornin’ Comin’ Down” in 1969. The No. 1 hit spot was reserved for Johnny Cash’s rendition. His cover was featured live and on The Johnny Cash Show album. It was even featured on Columbo in the 1974 episode, Swan Song. It was later featured on Kristofferson’s self-titled album in 1969. Jerry Lee Lewis, Gretchen Wilson, Willie Nelson, Lynn Anderson, and more artists recorded covers of the tune.

Kristofferson wrote the song while he was a janitor at Columbia Records, according to Song Facts. He worked as a janitor in order to break into the songwriting industry. Prior to his janitorial duty, he had a master’s degree from Oxford University and was a Captain in the United States army.

  • Album: Various
  • Year: 1969
  • Standout lyric: “And found my cleanest dirty shirt”
  • Awards: CMA Song of the Year

“Me and Bobby McGee”

Kris Kristofferson and Fred Foster co-wrote the rock crossover tune. Foster told his co-writer about a secretary on Music Row named “Bobbie” McKee. Kristofferson misheard him and thought he heard the song title as, “Me and Bobby McGee.” It stuck.

Roger Miller first recorded the song in 1969. It peaked at No. 12 on the country chart and grew interest. Before long, Charley Pride and Kenny Rogers covered the tune. Janis Joplin posthumously released her version which reached No. 1, her only chart-topper. The feat was on the all-genre Billboard Hot 100 chart. Now, countless artists have covered the song like Dolly Parton, Johnny Cash, Olivia Newton-John, The Grateful Dead, and more.

  • Album: Pearl
  • Year: 1971
  • RIAA: Platinum
  • Standout lyric: “Freedom’s just another word for nothin’ left to lose / Nothin’, it ain’t nothin’ honey, if it ain’t free”
  • Awards: Grammy Hall of Fame Award

“Help Me Make It Through the Night”

Kristofferson first recorded the song for his 1970 album. Months later, Sammi Smith recorded a version on her album of the same name. It reached No. 1 months later.

In 1980, Willie Nelson released his cover, which peaked at No. 1 in Canada and the United States. Gladys Knight also made a soul rendition that charted on both the all-genre and soul charts.

  • Album: Various
  • Year: 1970
  • Standout lyric: “I don’t care who’s right or wrong, I don’t try to understand”
  • Awards: Grammy Best Female Country Vocal Performance and CMA Single of the Year
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