Kris Kristofferson had an entirely different career as an Army captain and helicopter pilot before switching to country music -- and we're so glad he made the move. The tunesmith has bestowed on country music some of the biggest hits of the past several decades.

The Boot's list of the Top 10 Kris Kristofferson Songs includes everything from Top 40 singles to songs made famous by other artists -- but all are beloved tunes that involve the iconic singer-songwriter in some way:

  • 10

    "Good Morning John"

    Kristofferson wrote "Good Morning John" in response to his good friend Johnny Cash's ongoing struggle with addiction. At a party celebrating Cash's sobriety, friends were invited to write a letter, but Kristofferson chose to write a song instead.

    "Everyone was supposed to say something inspirational, so I wrote a song," Kristofferson tells Billboard. "I tried to record this once before with Wilie Nelson and my band. When I sang the chorus, they echoed me when I would sing "Good morning John." When I got to the line that said
    "I love you, John," Willie said "He loves you, John," and we all cracked up laughing. We never finished it, so I finished it myself."

  • 9

    "Feeling Mortal"

    "Feeling Mortal" is the title track of Kristofferson's 2013 album, and his reflection on his illustrious career in country music and the unstoppable passage of time. With lines that include, "God Almighty, here I am / Am I where I ought to be? / I’ve begun to soon descend / Like the sun into the sea / And I thank my lucky stars / From here to eternity / For the artist that you are / And the man you made of me," Kristofferson said the song was meant to be an encouragement.

    "It’s amazing," he tells CMT. "We don’t think about dying or anything, although all of us end up there. I guess when you get to be 76 years old, you start thinking about the shortness of the time left, but amazingly I do without regret."

  • 8

    "To Beat the Devil"

    "To Beat the Devil" was also written for Cash, after Kristofferson found the Man in Black drunk in a recording studio.

    "While he was reciting some poetry to me that he'd written, I saw that he was about a step away from dyin', and I couldn't help but wonder why," Kristofferson says of the song, which was released in 1970. "And the lines of this song occurred to me. I'm happy to say he's no longer wasted, and he's got him a good woman."

  • 7


    "Highwayman" was the title track of the first album of the group, made up of Kristofferson, Cash, Nelson and Waylon Jennings, known as the Highwaymen. Although the song was written by Jimmy Webb, the tune became a No. 1 hit for the group -- their only No. 1 single.

  • 6

    "They Killed Him"

    "They Killed Him" was included on Kristofferson's 1985 Repossessed album as an homage to his own heroes, including Jesus Christ, Martin Luther King Jr. and Mohandas Gandhi, all martyrs. The passionate song, which includes the lines, "But he knew his duty, and the price he had to pay / Just another holy man who tried to make a stand / My God, they killed him," was also recorded by Cash and Bob Dylan.

  • 5

    "My Heart Was the Last One to Know"

    "My Heart Was the Last One to Know," written with Shel Silverstein, was one of the first songs that Kristofferson wrote. At the time, he was still working as a helicopter pilot, nursing wounds from a failed relationship and feeling discouraged about his inability to fully pursue his passion: music.

    "I probably wrote more with Shel than anybody," Kristofferson tells CMT. "I didn’t co-write much and not much even with Shel. He’d give me the idea for a song, and I’d go down to the Gulf of Mexico, where I was flying every other week, and try to work on the song. Then we’d come back, and I remember laughing about it. Shel had even convinced himself that he co-wrote the song, but actually I’d written the whole song. He’d given me the idea for it. But we did co-write some songs together."

  • 4

    "Help Me Make It Through the Night"

    Kristofferson was inspired to write this song after reading an interview with Frank Sinatra, in which Sinatra said that he believed in "booze, broads or a Bible … whatever helps me make it through the night." Kristofferson, who was living with Dottie West and her husband at the time, offered the song to West first -- and, initially, she declined.

    "Help Me Make It Through the Night" earned Kristofferson his first Grammy, for Best Country Song. West ultimately recorded the song, as did Elvis Presley, Ray Price, Lynn Anderson, Loretta Lynn, Charley Pride, Andy Williams, Olivia Newton-John, Cash and wife June Carter Cash and Sammi Smith, the latter of whom had a No. 1 hit with the song and also won a Grammy, for Best Country Vocal Performance, Female.

  • 3

    "Why Me"

    "Why Me" was inspired by a church service at which Kristofferson heard Larry Gatlin's "Help Me." The song, and the service, encouraged Kristofferson to find help for his troubled life. In the book, Classic Country Music: A Smithsonian Collection, Kristofferson says, "I'm kneeling there, 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 ... It was just a personal thing I was going through at the time. I had some kind of experience that I can't even explain."

    "Why Me" became Kristofferson's only chart-topping single as an artist. It was also recorded by Cash, George Jones, David Allan Coe, Merle Haggard and Conway Twitty.

  • 2

    "Sunday Morning Coming Down"

    Kristofferson wrote "Sunday Morning Coming Down," but Ray Stevens recorded it first -- one of the first times that Kristofferson heard someone else singing his material.

    “At the time Ray cut it, nobody had ever put that much money and effort into one of my songs,” Kristofferson tells The Boot. “He’s a wonderful singer. The first time I heard it, I had to leave the publishing house. I went out and sat on the steps and wept. Of course, the record company didn’t want him to put it out and go in that direction, because he was having success with those novelty songs at the time he cut it."

    Of course, Cash also recorded "Sunday Morning Coming Down," taking it all the way to the top of the charts and changing the entire trajectory of Kristofferson's career.

    “Up until, like, 1969 … until the time that John had that TV show [The Johnny Cash Show], I didn’t have any real success you could point at with my songs,” Kristofferson says. “After he recorded "Sunday Morning Coming Down," it was like a flood gate opened. All of a sudden I’m recording and doing films, and everybody is doing my songs.”

  • 1

    "Me & Bobby McGee"

    "Me & Bobby McGee" is perhaps the song that Kristofferson is best known for, and with good reason. The tune, which became a No .1 hit for Janis Joplin, was also recorded by myriad other artists, including Roger Miller, Kenny Rogers, the Statler Brothers, Dottie West, the Grateful Dead and Loretta Lynn, among others. Kristofferson originally wrote "Me & Bobby McGee" with a twist: The character Bobby was actually a woman; however, when Joplin recorded it, she made Bobby a man.

    “The first time I heard Janis Joplin’s version was right after she died," Kristofferson told Performing Songwriter. "Paul Rothchild, her producer, asked me to stop by his office and listen to this thing she had cut. Afterwards, I walked all over L.A., just in tears. I couldn’t listen to the song without really breaking up. So when I came back to Nashville, I went into the Combine [Publishing] building late at night, and I played it over and over again, so I could get used to it without breaking up."

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