Kris Kristofferson

Following years of early hardship, Kris Kristofferson developed into a leading figure among 1970s performers in both music and cinema, eventually extending his reputation into a sustained Hollywood presence. Tracks such as “Me and Bobby McGee,” “Help Me Make It Through the Night,” “Sunday Mornin’ Comin’ Down,” and “For the Good Times” became major successes that shifted country music toward greater personal depth and gravity, qualities central to the outlaw country style he helped shape. Although the majority of his initial long-form releases placed inside the country Top Ten—with 1972’s Jesus Was a Capricorn reaching the summit—his compositions secured his initial foothold: Johnny Cash received a 1970 Country Music Award for “Sunday Mornin’ Comin’ Down,” Sammi Smith earned a Grammy for her 1970 interpretation of “Help Me Make It Through the Night,” and Janis Joplin scored a posthumous chart triumph with “Me and Bobby McGee” in 1971. He shared two Grammy wins in 1973 and 1975 for joint work with then-wife Rita Coolidge. His growing stature as a writer drew Hollywood interest, which produced an extended acting career. After claiming the Golden Globe for his lead performance opposite Barbra Streisand in 1976’s A Star Is Born, he appeared in projects directed by Martin Scorsese, Sam Peckinpah, and John Sayles, while further elevating his visibility through the Blade Trilogy. In 1984 he joined Johnny Cash, Waylon Jennings, and Willie Nelson to form the outlaw country supergroup the Highwaymen, and he kept issuing reflective Americana recordings including 2006’s This Old Road, 2009’s Closer to the Bone, and 2016’s Grammy-nominated The Cedar Creek Sessions. Inducted into the Country Music Hall of Fame in 2004 and honored with a 2014 Grammy Lifetime Achievement Award, Kristofferson stepped away from performing in 2021.

Born the oldest of three children to an Air Force major general who later directed air operations for Aramco in Saudi Arabia, Kristofferson grew up primarily in Brownsville, Texas, although the family relocated repeatedly before settling in San Mateo, California during his junior-high years. He completed San Mateo High School in 1954 and enrolled at Pomona College in Claremont, California, where he majored in creative writing and captured first prize plus three additional placements in an Atlantic Monthly–sponsored collegiate short-story competition. Phi Beta Kappa upon graduation in 1958, he obtained a Rhodes scholarship that took him to Oxford University. While there he composed and performed original material that attracted manager Larry Parnes, who represented Tommy Steele and other British pop acts. Under the Parnes contract he cut sides for Top Rank Records with producer Tony Hatch—recordings that remained unreleased—and performed as Kris Carson, yet achieved no commercial traction.

After receiving a master’s degree in English literature from Oxford in 1960, Kristofferson planned to remain for further study. During a holiday return to California, however, he rekindled a relationship with former girlfriend Fran Beir and the two married, prompting him to forgo Oxford and enlist in the Army. Following his father’s example, he trained as a helicopter pilot and received an assignment to West Germany, where he relocated with his wife and their daughter. Throughout the early 1960s he advanced to captain while resuming songwriting and performance, assembling a band that played service clubs. A fellow soldier encouraged him to submit material to the soldier’s relative, Nashville songwriter and publisher Marijohn Wilkin of Bighorn Music. Kristofferson followed the suggestion and received supportive feedback. In 1965 he was posted to West Point as an English instructor. During a two-week leave that June he visited Nashville, conferred again with Wilkin, and chose to pursue country songwriting instead. He resigned his commission, moved his family to Nashville, signed with Bighorn, and supplemented a modest weekly stipend through janitorial work, bartending, and helicopter flights to offshore oil rigs in the Gulf of Mexico. The marriage eventually ended in divorce.

Kristofferson achieved his first songwriting placement when Dave Dudley recorded “Viet Nam Blues,” which reached the country Top 20 in April 1966. As a performer he signed with Epic Records and issued the 1967 single “Golden Idol”/“Killing Time,” which failed to chart; both tracks later appeared on his album Surreal Thing. Roy Drusky took “Jody and the Kid” into the country Top 40 in summer 1968, and Billy Walker & the Tennessee Walkers placed “From the Bottle to the Bottom” inside the country Top 20 in April 1969. By that spring these three modest showings plus the unsuccessful single represented the sum of nearly four years’ effort in Nashville. He had moved to Fred Foster’s Columbine Music and begun occasional collaborations with Foster. A breakthrough arrived when Roger Miller chose to record their composition “Me and Bobby McGee,” a ballad that echoed Miller’s earlier hit “King of the Road” while incorporating a hippie perspective. Miller ultimately cut not only that song but also “Best of All Possible Worlds” and “Darby’s Castle” for his August 1969 album Roger Miller; the title track single reached the country Top 20. Meanwhile Kristofferson gained live exposure after Johnny Cash introduced him at the Newport Folk Festival and featured him on a network television broadcast.

In September 1969 Ray Stevens released “Sunday Mornin’ Comin’ Down,” which appeared on both pop and country charts. The following month Faron Young issued the Kristofferson–Shel Silverstein collaboration “Your Time’s Comin’,” which peaked inside the country Top Five in December 1969. Jerry Lee Lewis’s version of another Kristofferson–Silverstein song, “Once More with Feeling,” nearly topped the country charts in March 1970.

Fred Foster, who also operated Monument Records, signed Kristofferson to the label. The resulting debut album Kristofferson, issued in April 1970, contained the artist’s own readings of songs already recorded by others—“Me and Bobby McGee,” “Best of All Possible Worlds,” “Darby’s Castle,” “Sunday Mornin’ Comin’ Down”—alongside new compositions such as the romantically charged “Help Me Make It Through the Night” and “For the Good Times.” Promotion included a debut Troubadour engagement in Los Angeles on 23 June, an appearance at the Isle of Wight Festival on 26 July, and a Bitter End residency in New York in August. Despite positive notices the album sold modestly and soon went out of print.

Demand for his material nevertheless intensified. The same month Kristofferson appeared, Ray Price charted with “For the Good Times,” which reached country number one in September, crossed to the pop Top 20, and was named Song of the Year by the Academy of Country Music. In August Waylon Jennings placed “The Taker” in the country Top Five; the single also crossed to pop. Johnny Cash’s rendition of “Sunday Morning Coming Down” (restoring the dropped “g”) hit country number one in October, crossed over, and captured the Country Music Association’s Song of the Year Award for 1970—placing Kristofferson in the unusual position of winning the same honor from both major country organizations for different songs in the same year.

Further successes followed. In December Sammi Smith’s version of “Help Me Make It Through the Night” entered the country charts, eventually reaching the pop Top Ten, earning gold certification, and giving Kristofferson a third country number one in February 1971. Bobby Bare’s “Come Sundown” reached the country Top Ten in February 1971. Janis Joplin’s posthumous album Pearl, released in January 1971, featured her cover of “Me and Bobby McGee,” which ascended to pop number one in March. Ray Price followed with “I Won’t Mention It Again,” which supplied Kristofferson’s fourth country number one within eight months. Joe Simon charted pop with “Help Me Make It Through the Night” in April, Bobby Bare reached the country Top Ten in July with “Please Don’t Tell Me How the Story Ends,” and Peggy Little entered the country charts with “I’ve Got to Have You.”

Monument’s acquisition by CBS Records placed Kristofferson under Columbia distribution. His second album, The Silver Tongued Devil and I, arrived in July 1971 and combined earlier hits—“Jody and the Kid,” “The Taker”—with new material, notably “Loving Her Was Easier (Than Anything I’ll Ever Do Again),” which Roger Miller quickly took into the country Top 40. The release reached the country Top Five, the pop Top 20, and earned gold certification; Kristofferson’s own single version became a pop Top 40 and easy-listening Top Five hit. In August Monument reissued the debut album as Me and Bobby McGee, which now attained the country Top Ten, the pop Top 100, and gold status. Ray Price’s “I’d Rather Be Sorry” nearly topped the country charts in October while crossing to pop; Patti Page also charted country with the song. Jerry Lee Lewis placed “Me and Bobby McGee” on the charts for a third time in November, securing country airplay as the B-side of the number-one single “Would You Take Another Chance on Me” and pop Top 40 success on the flip. O.C. Smith reached the pop charts with “Help Me Make It Through the Night” that same month.

Kristofferson traveled to Peru at the request of director Dennis Hopper and made his screen debut in a small role in The Last Movie, released in September 1971, for which he also supplied songs. Footage from his Isle of Wight performance later appeared on the 1971 triple album First Great Rock Festivals of the Seventies and, in 1997, on the film and soundtrack Message to Love: The Isle of Wight. A more substantial part followed in Cisco Pike, released early in 1972, again allowing him to perform several compositions. Border Lord, issued in February 1972, contained only new material and reached the pop Top 100 and country Top Ten; its single “Josie” charted modestly. In March three of his songs—“For the Good Times,” “Help Me Make It Through the Night,” and “Me and Bobby McGee”—received Grammy nominations for Best Country Song, while the latter two were also nominated for Song of the Year. He won Best Country Song for “Help Me Make It Through the Night.” Gladys Knight & the Pips returned that song to the pop Top 40 and R&B Top 20 in March. An April live recording appeared on Big Sur Festival/One Hand Clapping. Sammi Smith’s version of “I’ve Got to Have You” reached the country Top 20 in September 1972 and crossed to pop.

Nine months after Border Lord, Jesus Was a Capricorn arrived in November 1972. Initial singles fared modestly, yet “Why Me” topped the country charts in July 1973, went gold, and crossed to the pop Top 20, propelling the album to country number one a year after release. Brenda Lee’s cover of “Nobody Wins” became a country Top Five hit. Kristofferson simultaneously expanded his acting roles. In 1973 he appeared in Paul Mazursky’s Blume in Love, contributing songs, and co-starred as Billy the Kid in Sam Peckinpah’s Pat Garrett and Billy the Kid; reviews praised his performances more than the films themselves.

On 19 August 1973 he married Rita Coolidge, who soon gave birth to their daughter. The couple’s debut duo album Full Moon, released the following month, topped the country charts, reached the pop Top 40, and earned gold certification. Its single “A Song I’d Like to Sing” became an easy-listening Top 20 and pop Top 40 hit. “Loving Arms” also charted across formats. Their version of “From the Bottle to the Bottom” won the 1973 Grammy for Best Country Vocal Performance by a Duo or Group. Kristofferson received additional 1973 Grammy nominations for “Why Me.”

Marilyn Sellars took the Kristofferson–Marijohn Wilkin composition “One Day at a Time” to the country Top 20 in April 1974 and the pop Top 40 later that year. Spooky Lady’s Sideshow, released in May, reached the country Top Ten but only the pop Top 100 and produced no charting single. Ronnie Milsap revived “Please Don’t Tell Me How the Story Ends” to country number one in September. Kristofferson appeared in Sam Peckinpah’s Bring Me the Head of Alfredo Garcia and Martin Scorsese’s Alice Doesn’t Live Here Anymore. The second Coolidge duo album Breakaway reached the country Top Five and pop Top 100; “Rain” charted country and easy listening, while “Lover Please” won a second Grammy for the duo.

Who’s to Bless and Who’s to Blame appeared in November 1975 and charted modestly in country, yet Johnny Duncan’s version of “Stranger” reached the country Top Five. Subsequent film work included Vigilante Force and The Sailor Who Fell from the Sea. Surreal Thing, issued eight months later, performed similarly. December 1976 brought both the box-office success A Star Is Born—second only to Rocky among that year’s releases—and the platinum soundtrack that topped the pop charts. Although Streisand dominated the project, Kristofferson received a Golden Globe for Best Actor.

Monument capitalized with the 1977 compilation Songs of Kristofferson, which reached the country Top Ten and pop Top 100 and earned gold status. After completing Semi-Tough he released Easter Island in March 1978, which improved slightly on prior chart positions. He starred in Convoy that summer. The third Coolidge duo album Natural Act appeared in January 1979.

Personal and professional circumstances declined in the late 1970s and early 1980s. Shake Hands with the Devil (September 1979) failed to chart despite a country single. Freedom Road received only television broadcast. Kristofferson and Coolidge divorced in December 1979. Song catalog activity remained strong: Lena Martell’s “One Day at a Time” hit number one in the U.K., and Cristy Lane’s version topped the U.S. country charts in June 1980. Willie Nelson Sings Kris Kristofferson reached the country Top Five, as did Nelson’s single of “Help Me Make It Through the Night.” Kristofferson toured with Nelson. Heaven’s Gate, released November 1980, proved a critical and financial disaster that bankrupted its studio; Rollover followed in 1981, after which feature-film offers diminished until 1984. To the Bone (January 1981) missed the pop charts but briefly entered country. Tompall & the Glaser Brothers nearly topped country with “Lovin’ Her Was Easier” in July.

The double album The Winning Hand, credited to Kris, Willie, Dolly & Brenda, appeared in November 1982 and reached the country Top Five. Kristofferson married attorney Lisa Meyers in February 1983; they later had five children. Television and theatrical films resumed in 1984 with The Lost Honor of Kathryn Beck, Flashpoint, and Songwriter, the latter co-starring Willie Nelson and earning Kristofferson an Academy Award nomination for original song score. Columbia issued Music from Songwriter, which charted pop and country Top 20; the duet “How Do You Feel About Foolin’ Around” entered the country singles chart.

The Highwaymen—Kristofferson, Nelson, Cash, and Jennings—debuted with Highwayman in April 1985. The title track, written by Jimmy Webb, topped country in August; the album also reached number one and went gold. “Desperados Waiting for a Train” reached the country Top 20. After legal settlement the name Highwaymen became official. Trouble in Mind (December 1985) featured Kristofferson’s theme “El Gavilan,” later included on Repossessed (February 1987), which spent six months on the country charts; “They Killed Him” also charted. He appeared in the television miniseries Amerika. Highwayman 2 (February 1990) reached the country Top Five and earned a Grammy nomination; its single “Silver Stallion” charted country Top 40. Third World Warrior (March 1990) failed to chart. Columbia/Legacy released the 1991 compilation Singer/Songwriter and the 1992 concert set Live at the Philharmonic. Kristofferson scored and appeared in the 1993 film Cheatin’ Hearts. The Highwaymen’s The Road Goes on Forever charted country in April 1995. A Moment of Forever, recorded earlier for Karambolage, finally appeared on Justice Records in August 1995. The Austin Sessions followed in 1999.

Kristofferson’s supporting role as a corrupt sheriff in John Sayles’s 1996 film Lone Star revitalized his screen career, leading to character parts and villain roles in major-studio releases such as Fire Down Below, Blade, and Payback, plus critical notice in A Soldier’s Daughter Never Cries and Limbo.

He returned to music with Broken Freedom Song on Oh Boy Records in 2003. This Old Road (2006) and Closer to the Bone (2009), both produced by Don Was for New West, reached the Top 20 of Billboard’s Independent Albums chart. Feeling Mortal (2013) peaked at number nine on the folk chart. The Cedar Creek Sessions, recorded in Austin, earned a 2016 Grammy nomination for Best Americana Album. He contributed a track to Brandi Carlile’s 2017 charity album Cover Stories. After performing at Joni Mitchell’s 2018 75th-birthday concert and the 2020 Outlaw Country Cruise, Kristofferson retired quietly in January 2021. He died at his home in Maui, Hawaii, on 28 September 2024, surrounded by family; he was 88.