From Soldier to Songwriter: The Remarkable Journey of Kris Kristofferson

Few stories are as compelling as that of Kris Kristofferson. A man who seemed destined for a career in the military or academia instead found his true calling as a songwriter and recording artist.

Born into a military family, Kristofferson was the son of an Air Force Major General. He served as a Captain and helicopter pilot in the U.S. Army, and his academic prowess earned him a Rhodes Scholarship to study literature at Oxford University after completing his undergraduate degree at Pomona College in California. By all accounts, his path seemed clear: he was two weeks away from teaching English literature at West Point. 


But fate had other plans. Kristofferson resigned his commission and headed to Nashville, fueled by a dream of becoming a professional songwriter. In Music City, he found early support from publisher Marijohn Wilkin at Buckhorn Music, and later from Fred Foster and Bob Beckham at Combine Music. Like many aspiring artists, he paid his dues working part-time jobs, including a stint as a janitor at Columbia Studios. It was during this time that an unknown Kristofferson could be found sweeping floors and emptying ashtrays while Bob Dylan recorded his seminal Blonde on Blonde album. 


Kristofferson was crafting a unique songwriting style, drawing inspiration from the Romantic poets, New York’s Greenwich Village folk scene, and fellow Texan songwriter Mickey Newbury. His songs captured the spirit of a turbulent era, speaking to themes of personal freedom, emotional honesty, and raw sensuality.


In 1969, Roger Miller recorded Kristofferson’s "Me and Bobby McGee," reaching #12 on the country charts. The following year, Ray Price took "For the Good Times" to the top of the country charts, crossing over to peak at #11 on the pop charts. Bobby Bare also found success with Kristofferson’s "Come Sundown," which cracked the country Top Ten in 1970. 

One of Kristofferson’s musical heroes, Johnny Cash, inspired the song "The Pilgrim." After several unsuccessful attempts to pitch Cash "Sunday Morning Coming Down," Kristofferson famously piloted a helicopter and landed it in Cash’s backyard to get his attention. The song became a #1 country hit for Cash and the Country Music Association’s 1970 Song of the Year. 


The year 1971 was particularly fruitful for Kristofferson. Sammi Smith’s rendition of "Help Me Make It Through the Night," a song encouraging a one-night stand, topped the charts and won Kristofferson a Grammy for Best Country Song. Smith also won a Grammy for Best Country Vocal Performance, Female, and a CMA for Single of the Year. That same year, Janis Joplin’s rendition of "Me and Bobby McGee" became a #1 pop hit. 


Kristofferson’s success inspired a new generation of songwriters. Guy Clark, known for songs like "L.A. Freeway" and "Desperadoes Waiting for a Train," cited hearing Kristofferson’s "Me and Bobby McGee" on the radio as a pivotal moment in his own decision to move from Los Angeles to Nashville in 1971. 


As the 1970s progressed, Kristofferson continued to score hits with songs like "Please Don’t Tell Me How the Story Ends," a #1 hit for Ronnie Milsap in 1974. He also became a hit recording artist himself, with songs like "Loving Her Was Easier (Than Anything I’ll Ever Do Again)" and the gospel-influenced "Why Me," which was his only country chart-topper as a recording artist. 

Kristofferson’s partnership with Rita Coolidge, to whom he was married from 1973 to 1980, produced several duet albums and won two Grammys for Best Country Vocal Performance by a Duo or Group. Their recordings of "From the Bottle to the Bottom" and "Lover Please" were particularly successful. 


In 1985, Kristofferson joined forces with Johnny Cash, Waylon Jennings, and Willie Nelson to form the Highwaymen. Their recording of "Highwayman," penned by Jimmy Webb, became another hit and further cemented Kristofferson’s place in country music history. 

Beyond music, Kristofferson has had a prolific acting career, appearing in numerous films and television movies. His roles in Pat Garrett and Billy the Kid (1973), Alice Doesn’t Live Here Anymore (1974), and Songwriter (1984) showcased his versatility. His performance in the 1976 remake of A Star is Born alongside Barbra Streisand earned him a Golden Globe for Best Actor – Motion Picture Musical or Comedy. 


Today, Kristofferson remains a respected figure in American music, as well as outspoken advocate for social justice and human rights, he was named Veteran of the Year by the American Veteran Awards in 2002. His journey from soldier to songwriter is a testament to following one’s passion, no matter the obstacles.


Join us this evening (Saturday June 22, 2024) to celebrate Kris Kristofferson’s 88th birthday with a special one-hour program beginning at:






12 PM (Sunday) AEST

2 PM (Sunday) NZST


You can hear Kris Kristofferson as well as the songs he has written every day on Real Wild Radio. Download our Free App and listen from anywhere.  Simply visit your App Store, search for Real Wild Radio, download and tune in. 


Real Wild Radio is a 501[c][3] Non-Profit Corporation. Our Mission is to entertain and educate our listeners on the history of Country, Western and Bluegrass Music while introducing and promoting current Roots and Ameripolitan artists. Our programming is made possible by our generous Donors and Underwriters. Support our mission by making a tax-deductible donation or becoming a station Underwriter at 


If you have any questions please send us a message.


Thanks for listening.

Stay Real. Stay Wild. 


#KrisKristofferson #CountryMusicHistory #Birthday