His songs "Me and Bobby McGee," "Help Me Make It Through the Night," "Sunday Mornin' Comin' Down," and "For the Good Times," all chart-topping hits, helped redefine country songwriting, making it more personal and serious, much in the way that Bob Dylan's songs had transformed pop music songwriting in the mid-'60s. By 1987, it was estimated that Kristofferson's compositions had been recorded by more than 450 artists. His renown as a songwriter enabled him to launch a moderately successful career as a musical performer and that, in turn, brought him to the attention of Hollywood, leading to a lengthy career as a film actor.

The eldest of three children of an Air Force major general who retired from the military to head up air operations for the Saudi Arabian company Aramco, Kristofferson spent most of his childhood in Brownsville, TX, though his family moved around, finally settling in San Mateo, CA, by his junior high-school years. He graduated from San Mateo High School in 1954 and entered Pomona College in Claremont, CA. There he studied creative writing and he won first prize and three other placements in a collegiate short-story contest sponsored by Atlantic Monthly magazine. He graduated Phi Beta Kappa in 1958, having secured a prestigious Rhodes scholarship to continue his studies at Oxford University in England. While at Oxford, he wrote and performed his own songs, which brought him to the attention of manager Larry Parnes (who handled Tommy Steele and other British pop stars). Signing with Parnes, he made recordings for Top Rank Records produced by Tony Hatch (apparently never released) and performed under the name Kris Carson, but he was not successful.

After earning a master's degree in English literature from Oxford in 1960, Kristofferson intended to continue his studies there. But during a Christmas break back home in California, he resumed his relationship with an old girlfriend, Fran Beir, and they married. Instead of returning to Oxford, he joined the Army. Like his father, he became a pilot, learning to fly helicopters. He was assigned to West Germany and went there with his wife and their daughter. During the early '60s, while rising to the rank of captain, he eventually returned to writing and performing, organizing a soldiers' band to play at service clubs. Hearing his songs, a friend suggested sending them to a relative of his, the Nashville songwriter Marijohn Wilkin. Kristofferson did so and he received encouragement from Wilkin, who had become a music publisher by founding Bighorn Music. In 1965, Kristofferson was reassigned to the West Point military academy, where he was to become an English instructor. He spent a two-week leave in June 1965 in Nashville, where he looked up Wilkin and decided to try to become a country songwriter instead. He resigned his commission and moved his family to Nashville, signing to Bighorn, which gave him a small weekly stipend that he augmented with a variety of jobs, including janitorial work, bartending, and flying helicopters to and from offshore oil rigs in the Gulf of Mexico. He and his wife had a son who was born with a defective esophagus, resulting in thousands of dollars in medical bills. Eventually, the couple divorced.

Kristofferson scored his first success as a songwriter with "Viet Nam Blues," which was recorded by Dave Dudley and peaked in the country Top 20 in April 1966. As a recording artist, Kristofferson was signed to Epic Records and released a lone single, "Golden Idol"/"Killing Time," in 1967, but it missed the charts. (He later re-recorded both songs for his Surreal Thing album.) Roy Drusky recorded Kristofferson's "Jody and the Kid" and took it into the country Top 40 in the summer of 1968 and Billy Walker and the Tennessee Walkers' version of his "From the Bottle to the Bottom" peaked in the Top 20 of the country charts in April 1969. But by that spring, those three chart placings and his failed single were all Kristofferson had to show for almost four years of effort in Nashville. He had moved to Fred Foster's Columbine Music and begun to collaborate occasionally with Foster, and he got a break when Roger Miller decided to record one of their songs, "Me and Bobby McGee," a ballad about hoboing that recalled earlier Miller hits like "King of the Road," but with more of a hippie slant. Miller ended up recording not only "Me and Bobby McGee," but also two other Kristofferson compositions, "Best of All Possible Worlds" and "Darby's Castle," for his August 1969 album, Roger Miller. "Me and Bobby McGee" was released as a single in advance of the album and it peaked in the country Top 20. Meanwhile, Kristofferson had begun to gain recognition as a performer, thanks to Johnny Cash, who introduced him at the Newport Folk Festival that summer and featured him on his network television show.

In September 1969, Kristofferson earned another important cover when Ray Stevens released a version of his reflection on a hangover, "Sunday Mornin' Comin' Down," as a single. It entered both the pop and country charts. The following month, Faron Young released "Your Time's Comin'," co-written by Kristofferson and Shel Silverstein. It gave the songwriter his biggest hit so far when it peaked in the country Top Five in December 1969. Jerry Lee Lewis' recording of Kristofferson and Silverstein's "Once More with Feeling" did even better, just missing the top of the country charts in March 1970.

In addition to Columbine Music, Fred Foster also ran Monument Records, an independent label, and he signed Kristofferson to it as a recording artist. Kristofferson went into the studio and cut his own versions of some of the songs others had already done -- "Me and Bobby McGee," "Best of All Possible Worlds," "Darby's Castle," "Sunday Mornin' Comin' Down" -- as well as some new songs, notably "Help Me Make It Through the Night" and "For the Good Times," both romantic ballads with a decidedly erotic tone. His debut album, titled Kristofferson, was released in April 1970 and he promoted it with his first major concert tour, debuting at the Troubadour in Los Angeles on June 23, appearing at the giant Isle of Wight Festival on July 26, and playing the Bitter End in New York in August. But even at a time when standards for singers had fallen noticeably, the album was criticized for Kristofferson's rough vocals; it sold poorly and quickly went out of print.

The demand for his songs, however, only increased. The same month that Kristofferson was released, Ray Price reached the country charts with "For the Good Times," though it had been intended as the B-side of the single. It hit number one in September and crossed over to the pop charts, where it reached the Top 20; as a result, "For the Good Times" was named Song of the Year for 1970 by the Academy of Country Music. In August, Waylon Jennings reached the country charts with Kristofferson and Silverstein's "The Taker," which peaked in the Top Five in October and crossed over to the pop charts. By then, Johnny Cash had entered the country charts with his version of "Sunday Morning Coming Down" (as he called it, restoring the dropped "g"s). It hit number one in October and crossed over to the pop charts, and that same month it won the Country Music Association's Song of the Year Award for 1970, putting Kristofferson in the unusual position of winning the same award from country's two rival organizations for the same year with different songs.

But the string of hits was far from over. In December, Sammi Smith entered the country charts with "Help Me Make It Through the Night," giving the song a surprising twist by having the woman ask the man to sleep with her instead of the other way around. The single crossed over to the pop charts, eventually reaching the Top Ten and going gold, and it gave Kristofferson his third country chart-topper in February 1971. Meanwhile, Bobby Bare's recording of Kristofferson's "Come Sundown" also had reached the country charts in December and it peaked in the Top Ten in February 1971. Up to this point, Kristofferson had been getting most of his recognition in country music, but that changed in January 1971 when Janis Joplin's posthumous album Pearl was released. Joplin had covered "Me and Bobby McGee" and it was released as a single, shooting up the pop charts to number one in March. That same month, Ray Price followed "For the Good Times" with another Kristofferson song, "I Won't Mention It Again," which crossed over to the pop charts and in May gave the songwriter his fourth country number one hit within eight months. Meanwhile, Joe Simon got into the pop charts with his version of "Help Me Make It Through the Night" in April, Bobby Bare charted country in May with Kristofferson's "Please Don't Tell Me How the Story Ends," which peaked in the Top Ten in July, and Peggy Little reached the country charts with his "I've Got to Have You."

Despite all this sudden success as a songwriter, Kristofferson had not yet achieved any great notice as a performer. Monument had been purchased by CBS Records and turned into a subsidiary of the Columbia label, giving its artists the benefit of major-label distribution and promotion. Kristofferson released his second album, The Silver Tongued Devil and I, in July 1971. Again, it combined the songwriter's own versions of songs that had scored for others -- "Jody and the Kid," "The Taker" -- with important new work, notably the ballad "Loving Her Was Easier (Than Anything I'll Ever Do Again)," which Roger Miller quickly covered for a Top 40 country hit. The album finally broke Kristofferson as a recording artist, rising into the Top Five of the country charts and the Top 20 of the pop charts and going gold, with the songwriter's own version of "Loving Her Was Easier (Than Anything I'll Ever Do Again)" becoming a Top 40 pop and Top Five easy listening hit. In August, Monument re-released Kristofferson's first album, renaming it Me and Bobby McGee. This time, the LP reached the country Top Ten and the pop Top 100 and went gold. Meanwhile, Ray Price released his third consecutive single of a Kristofferson song, "I'd Rather Be Sorry," and it just missed topping the country charts in October while crossing over to the pop charts. Patti Page also made the country charts with her version of the song. Jerry Lee Lewis put "Me and Bobby McGee" into the charts for a third time in November; it was given some country airplay as the B-side of his number one country single "Would You Take Another Chance on Me," while pop radio flipped the disc over and made it a Top 40 pop hit. The same month, O.C. Smith got into the pop charts with his version of "Help Me Make It Through the Night."

Kristofferson himself, meanwhile, had traveled to Peru at the behest of director Dennis Hopper, and he made his film debut in a bit part in The Last Movie, released in September, to which he also contributed songs. The same month, part of his performance from the Isle of Wight Festival was in the charts on the triple-record set First Great Rock Festivals of the Seventies: Isle of Wight/Atlanta Pop Festival. (In 1997, the film and CD Message to Love: The Isle of Wight also featured his appearance.) He had a more substantial film role in Cisco Pike, released early in 1972, also getting to sing several more of his songs. In February, he released his third album, Border Lord. It was his first collection to consist of all-new material and proved to be a slight commercial disappointment, reaching only the Top 100 of the pop charts and the Top Ten of the country charts, its single "Josie" becoming a pop and country chart entry but not a big hit. In March, however, three of his songs, "For the Good Times," "Help Me Make It Through the Night," and "Me and Bobby McGee," were among the five nominees for the 1971 Grammy Award for Best Country Song, while "Help Me Make It Through the Night" and "Me and Bobby McGee" were also up for the Song of the Year Grammy. Competing against himself, he managed to win his first Grammy for Best Country Song for "Help Me Make It Through the Night." The same month, Gladys Knight & the Pips brought the song back into the pop Top 40 and also made the R&B Top 20 with their rendition. In April, Kristofferson was in the charts with another live recording, appearing on the various-artists collection Big Sur Festival/One Hand Clapping. In June, Sammi Smith made the country charts with her version of "I've Got to Have You," which peaked in the Top 20 in September and also crossed over to the pop charts.

Having taken only seven months between his second and third albums, Kristofferson waited only nine more months before delivering his fourth album, Jesus Was a Capricorn, in November 1972. Initially, the LP did not do as well as Border Lord, itself a step down from The Silver Tongued Devil and I, as the title song barely made the pop singles charts and a second single, "Jesse Younger," missed the charts entirely. But in March 1973, Monument released a third single, the slow, pious "Why Me," which topped the country charts in July and went gold, also crossing over to the pop Top 20. With that, sales of Jesus Was a Capricorn rebounded and the album hit number one in the country charts a year after it was released. (Meanwhile, Brenda Lee had covered "Nobody Wins" from the album for a Top Five country hit and a pop chart entry.)

Kristofferson, meanwhile, had returned to acting, getting more substantial film roles and working with important directors. In 1973, he appeared in Paul Mazursky's Blume in Love, also contributing a couple of songs, and in Sam Peckinpah's Pat Garrett and Billy the Kid, co-starring as Billy the Kid in the latter. His notices tended to be better than those for the films themselves and indicated that he had a future in films.

On August 19, 1973, Kristofferson married singer Rita Coolidge (who soon bore him a second daughter) and the following month the couple released a duo album, Full Moon. It was a big hit, topping the country charts, reaching the Top 40 of the pop charts, and going gold. Its first single, Kristofferson's composition "A Song I'd Like to Sing," was a Top 20 easy listening hit, a Top 40 pop hit, and a country chart entry. "Loving Arms," a second single, made the easy listening Top 40 and also reached the pop and country charts. The couple's version of "From the Bottle to the Bottom" won the 1973 Grammy Award for Best Country Vocal Performance by a Duo or Group. (Due to the peculiarities of the Grammy eligibility rules, "Loving Arms" was nominated in the same category the following year.) Kristofferson also earned 1973 Grammy nominations for Best Country Song and Best Country Vocal Performance, Male, for "Why Me."

In April 1974, "One Day at a Time," written by Kristofferson and Marijohn Wilkin, reached the country charts in a recording by Marilyn Sellars that went on to peak in the Top 20. Later in the year, it reached the pop Top 40. Kristofferson's fifth album, Spooky Lady's Sideshow, was released in May. Compared to earlier releases, it was a commercial disappointment, reaching the Top Ten of the country charts but only the Top 100 of the pop charts, with no charting single. From this point on, Kristofferson's albums would be only modest sellers at best. But he remained a potent country songwriter. In July, Ronnie Milsap entered the country charts with a revival of "Please Don't Tell Me How the Story Ends"; by September it had topped the country charts and crossed over to the pop charts. Kristofferson continued to pursue his film career, taking a small part in Sam Peckinpah's Bring Me the Head of Alfredo Garcia, released in the summer and a co-starring role in Martin Scorsese's Alice Doesn't Live Here Anymore, which appeared in December. Also that month, Kristofferson and Coolidge released their second duo album, Breakaway. Though less successful than their first one, it reached the Top 100 of the pop charts and the Top Five of the country charts. The single "Rain" made the country and easy listening charts. "Lover Please" also got into the easy listening charts and it went on to win the duo a second Grammy for Best Country Vocal Performance by a Duo or Group.

Kristofferson took a break from moviemaking to concentrate on his musical career and his sixth album, Who's to Bless and Who's to Blame, released in November 1975. But the extra effort did not translate into increased sales. The LP reached the country Top 40, but it missed the Top 100 of the pop charts. Johnny Duncan's recording of the Kristofferson song "Stranger" from the album became a country hit, however, reaching the Top Five. Kristofferson returned to the movies and in the spring of 1976 was seen in Vigilante Force and The Sailor Who Fell From Grace With the Sea, also contributing a song to the latter. His seventh album, Surreal Thing, followed his sixth by only eight months. It was another commercial disappointment, reaching the country Top Ten while barely registering in the pop charts. But in December 1976, he enjoyed both a hit movie and a hit record with the release of A Star Is Born, in which he co-starred with Barbra Streisand. Critics howled, but the film was a box office smash, second only to Rocky among motion pictures released in 1976 as the top-grossing hit, while the soundtrack album, which featured several contributions from Kristofferson (among them the pop chart entry "Watch Closely Now"), topped the pop charts and sold several million copies. Of course, Streisand had more to do with all that than Kristofferson did, but he was awarded a Golden Globe for Best Actor.

Monument Records seized upon the occasion of his increased profile to release a compilation, Songs of Kristofferson, in April 1977. It did considerably better than his recent releases of new material, making the country Top Ten and the pop Top 100 and earning a gold record. Making only one film in 1977, Semi-Tough, released in the fall, he worked on his eighth album for more than a year and a half, not releasing Easter Island until March 1978. It marked a slight commercial uptick, charting higher in the pop and country charts than his previous effort, but did not restore his commercial fortunes as a recording artist. Returning to the movies, Kristofferson starred in Convoy, a film extrapolation of the 1976 song hit by C.W. McCall, which opened in the summer. In January 1979, he and Rita Coolidge released their third duo album, Natural Act, which was another modest seller.

Kristofferson's personal life and professional career were both at low points in the late '70s and early '80s. His ninth album, Shake Hands With the Devil, was released in September 1979 and did not sell well enough to reach the charts, though the single "Prove It to You One More Time Again" was a country singles chart entry. His next film, Freedom Road, was not given a theatrical release in the U.S., instead being broadcast on television in October. And on December 2, he and Rita Coolidge divorced. At the same time, however, his song catalog continued to prosper. Lena Martell's cover of "One Day at a Time" hit number one in the U.K. in October, then in the U.S. Cristy Lane revived the song, taking it to number one in the country charts in June 1980. Willie Nelson Sings Kris Kristofferson was released in October 1979 and made the country Top Five, as did Nelson's single release of "Help Me Make It Through the Night." Kristofferson toured with Nelson during the winter of 1979-1980. During this period, he also was working on what should have been his greatest cinematic triumph yet, though it turned into a debacle. This was Heaven's Gate, director Michael Cimino's follow-up to his Academy Award-winning film The Deer Hunter. The lengthy, expensive film debuted to negative reviews in November 1980 and was such a financial catastrophe that it bankrupted the movie studio that made it. Kristofferson had already been contracted to make another film, Rollover, released in 1981, but his association with Heaven's Gate may have scared off casting directors, since he didn't appear in another film until 1984. Meanwhile, he released his tenth album, To the Bone, in January 1981, and it became his second straight LP to miss the pop charts, though it made the country charts briefly, as did the single "Nobody Loves Anybody Anymore." But the old songs continued to sell; in July, Tompall and the Glaser Brothers just missed topping the country charts with their revival of "Lovin' Her Was Easier (Than Anything I'll Ever Do Again)."

Except for a non-charting single, "Here Comes That Rainbow Again"/"The Bandits of Beverly Hills," Kristofferson was not heard from for the rest of 1981 or most of 1982, resurfacing in November 1982 with the release of the double-album The Winning Hand, a group effort credited to "Kris [Kristofferson], Willie [Nelson], Dolly [Parton] & Brenda [Lee]." The album reached the country Top Five, though it failed to cross the 100 mark on the pop charts. On February 19, 1983, Kristofferson married for the third time, wedding attorney Lisa Meyers, with whom he eventually had five more children, for a total of eight. He returned to filmmaking in January 1984 with the television broadcast of The Lost Honor of Kathryn Beck, and made it back into movie theaters later that year with Flashpoint, a mystery, and Songwriter. In the latter, he co-starred with Willie Nelson in a story about the Nashville music industry. He wrote a number of songs for the film, resulting in his first Academy Award nomination for original song score. Columbia Records released Music From Songwriter, a duo album by Nelson and Kristofferson on which the two sang separately and shared a couple of duets. The album reached the pop charts and the Top 20 of the country charts, and one of the duets, Kristofferson's "How Do You Feel About Foolin' Around," made the country singles charts.

Kristofferson and Nelson expanded their partnership into a supergroup quartet with the addition of Johnny Cash and Waylon Jennings to create the album Highwayman, released in April 1985. The title track, a song about reincarnation written by Jimmy Webb, with each group member taking a verse, topped the country charts in August and the LP was also a number one country hit, going gold. A second single, Guy Clark's "Desperados Waiting for a Train," made the country Top 20. The recordings were billed to the four participants by name, but the group came to be known informally as "the Highwaymen," though a settlement had to be made with the 1960s folk group of the same name for the name to be used legally.

In December 1985, Kristofferson starred in Alan Rudolph's film Trouble in Mind, also contributing the theme song, "El Gavilan" ("The Hawk," after the name of his character), sung by Marianne Faithfull. He put the song on Repossessed, his first solo album in six years, which was released on Mercury Records in February 1987. Reflecting his left-wing views particularly on American military involvement in Central America, Repossessed spent six months in the country charts, and "They Killed Him," a tribute to Christ, Gandhi, and Martin Luther King, Jr., placed in the country singles charts. Simultaneous with the release of the LP, Kristofferson appeared in Amerika, a controversial weeklong television mini-series that fantasized a U.S. under Communist domination. It was one of many TV movie projects the actor had done in the mid-'80s, a time when his feature film work remained sparse.

Highwayman 2 appeared in February 1990, preceded by a single, "Silver Stallion," that made the country Top 40. The album reached the country Top Five and it earned a Grammy nomination for Best Country Vocal Collaboration. Kristofferson followed Repossessed with a second Mercury album, Third World Warrior, in March 1990. Another work of agitprop, it failed to reach the charts. In 1991, Columbia/Legacy released the compilation Singer/Songwriter, a double-CD set containing both Kristofferson's versions of his best-known songs and the best-known covers of them by people like Janis Joplin and Ray Price. The archival label followed in 1992 with the previously unreleased concert set Live at the Philharmonic, recorded in 1972. Kristofferson worked steadily in TV movies and independent features during the late '80s and early '90s; he wrote the score for the 1993 film Cheatin' Hearts, in which he also appeared. The Highwaymen's third album, The Road Goes on Forever, appeared in April 1995 and made the country charts. As a solo artist, Kristofferson had teamed with producer Don Was to record a new album, A Moment of Forever, for Was' Karambolage imprint in 1993, but an initial distribution deal fell through and the album was not released until August 1995, when it appeared on the Texan independent label Justice Records. Four years later, Kristofferson released The Austin Sessions, an album of remakes of his most popular songs. (In the mid-'90s, One Way Records reissued many of Kristofferson's Monument albums on CD.)

Kristofferson's appearance in director John Sayles' film Lone Star (1996) marked a turning point in his film career. Taking a supporting role as a corrupt sheriff, the 60-year-old actor displayed a flair for character parts and villains that vastly increased his offers from Hollywood in the late '90s and led to his appearances in such major-studio action features as Fire Down Below, Blade, and Payback. He also earned admiring critical notices as a James Jones-like novelist in A Soldier's Daughter Never Cries and in another Sayles film, Limbo. By the turn of the century, complaining that he hadn't had time to tour as a singer in years, Kristofferson was looking forward to additional film work.

Although his early work was frequently repackaged and released in new compilation packages, Kristofferson released very little new work as the 21st century dawned. A live set, Broken Freedom Song, appeared in 2003 on John Prine's Oh Boy Records, and another Don Was-produced album, This Old Road, saw the light of day in 2006 on New West Records. ~ William Ruhlmann