Kris Kristofferson. Photo: Courtesy of the Country Music Hall of Fame and Museum

Country Music Hall of Fame member Kris Kristofferson passed away at his home in Maui, Hawaii on Saturday (Sept. 28) at age 88.

One of the greatest songwriters in music history, he revolutionized Nashville with his lyrics’ frank sexuality, poetic structures and intellect. Kristofferson’s musical legacy includes such masterpieces as “Help Me Make It Through the Night,” “For the Good Times,” “Sunday Morning Coming Down,” “Why Me (Lord)” and “Me and Bobby McGee.” He had success as a solo recording artist, in a duet with Rita Coolidge and as a member of the country supergroup The Highwaymen with Johnny Cash, Waylon Jennings and Willie Nelson. Along the way, he earned four Grammy Awards and seven Gold records.

He graduated from music stardom to a thriving film career in such features as A Star Is Born, Alice Doesn’t Live Here Anymore, Pat Garrett and Billy the Kid, Semi-Tough and Blade. He was also a novelist, a poet, a short story writer and an essayist.

Kris Kristofferson was born in Texas, but the family moved several times because his father was in the military. A major general in the Air Force, he urged his son to emulate him. In high school in California, Kristofferson excelled in rugby, track, soccer, boxing and football. He was also a brilliant student. While enrolled in Pomona College, he had two essays published by The Atlantic Monthly. Elected to Phi Beta Kappa, he graduated summa cum laude, then became a Rhodes Scholar at Oxford University in England. While there, he began his recording career as “Kris Carson,” but that music went nowhere.

His father pressured him to join the Army. Kristofferson became a helicopter pilot while in the service. A fellow soldier was related to Nashville songwriter Marijohn Wilkin, who took an interest in Kristofferson’s music. The two later co-wrote the million-selling alcohol-recovery anthem “One Day at a Time.”

Instead of taking a position as an instructor at West Point, Kristofferson quit the Army and moved to Nashville in 1965. His parents reportedly disowned him. During his early years on Music Row, the singer-songwriter worked as a janitor at Columbia Studios and as a bartender at the Tally-Ho Tavern. He also flew helicopters for a Louisiana oil company. He’d write songs on an oil rig, then return to Nashville to pitch them. At one point, he landed a helicopter on Johnny Cash’s yard to get attention for his tunes. Songwriters Mickey Newbury, Shel Silverstein and Tom T. Hall befriended and encouraged him.

Kristofferson had his first Nashville success in 1966 when Dave Dudley had a hit with “Viet Nam Blues.” In 1968, Roy Drusky made the country charts with “Jody and the Kid.” In 1969, Roger Miller recorded “Me and Bobby McGee;” Faron Young had a top 10 hit with “Your Time’s Comin;’” Billy Walker scored with “From the Bottle to the Bottom,” and Ray Stevens had “Sunday Morning Coming Down.”

Major successes occurred the following year when Johnny Cash hit the top of the country charts with “Sunday Morning Coming Down;” Waylon Jennings scored with “The Taker;” Jerry Lee Lewis had a smash with “Once More With Feeling” and Ray Price had a massive pop crossover success with “For the Good Times.” The last was named the Country Music Association (CMA) Song of the Year. Meanwhile, the Academy of Country Music (ACM) bestowed its 1970 Song of the Year honor on “Sunday Morning Coming Down.”

Following a brief, unsuccessful stint at Epic Records, Kristofferson signed with Monument Records. His 1970 LP debut was packed with hits, including “Help Me Make It Through the Night,” a 1971 pop-crossover smash for Sammi Smith that earned the songwriter his first Grammy Award. That was also the year that Janis Joplin topped the pop charts with his “Me and Bobby McGee;” Ray Price scored with “I’d Rather Be Sorry” and Bobby Bare had back-to-back top 10 country hits with “Come Sundown” and “Please Don’t Tell Me How the Story Ends.” Sammi Smith returned to his catalog for her 1972 hit “I’ve Got to Have You.”

Kristofferson and Coolidge were married in 1973-80. She and Larry Gatlin sang backup on his gospel song “Why Me.” In the summer of 1973, it became his only No. 1 hit as an artist. The couple earned two Grammys for their recordings together.

Brenda Lee’s top 10 success with Kristofferson’s “Nobody Wins” in 1973 marked her transition from pop stardom to country hit maker. Ronnie Milsap’s revival of “Please Don’t Tell Me How the Story Ends” hit No. 1 on the country hit parade in 1974. Singers Marilyn Sellars and Don Gibson both recorded “One Day at a Time” that year, and the Sellars version became a top 20 country hit. In 1976, Johnny Duncan went into the top 10 with the songwriter’s “Stranger” (featuring vocal accompaniment by Janie Fricke). Kristofferson’s own recordings continued, with nine albums issued between 1972 and 1979.

Kris Kristofferson began his silver-screen career in the 1970s. Early credits included The Last Movie (1971), Cisco Pike (1972), Pat Garrett and Billy the Kid (1973), Blume In Love (1973), Alice Doesn’t Live Here Anymore (1974), Bring Me the Head of Alfredo Garcia (1974), The Sailor Who Fell from Grace with the Sea (1976) and Vigilante Force (1976). He co-starred with Barbra Streisand in 1976’s A Star Is Born, which earned him a Best Actor Golden Globe Award. Its soundtrack album sold more than four million copies. He went on to star in Semi-Tough (1977, with Burt Reynolds), Convoy (1978), Songwriter (1980, with Willie Nelson) and Heaven’s Gate (1980). His Songwriter soundtrack was nominated for an Oscar.

As a songwriter, he continued to be a force on the country charts. In 1980, Cristy Lane scored an No. 1 smash with “One Day at a Time.” Nelson recorded an entire album of Kristofferson songs and hit the top 10 in 1980 with his revival of “Help Me Make It Through the Night.” In 1981, The Glaser Brothers scored the biggest hit of their career with Kristofferson’s “Lovin’ Her Was Easier.” The songwriter had based that song on a Shakespeare sonnet.

Kristofferson teamed up with Nelson, Lee and Dolly Parton on the hit 1982 album The Winning Hand. The first Highwaymen all-star album was issued in 1984 and earned a Platinum record. The group scored major hits the following year with Jimmy Webb’s “Highwayman” and Guy Clark’s “Desperados Waiting for a Train.” Kristofferson, Cash, Nelson and Jennings issued two more collections and became a hugely popular concert attraction.

Toward the end of the decade, Kristofferson moved from Monument to Mercury Records. His Repossessed (1988) and Third World Warrior (1989) albums for Mercury illuminated his progressive, leftist political positions. One of his songs from this era endured: “They Killed Him” was an homage to Kristofferson’s martyred heroes Mahatma Ghandi, Martin Luther King Jr., John F. Kennedy, Robert F. Kennedy and Jesus Christ. Bob Dylan soon re-popularized it on his Knocked Out Loaded album.

The songwriter’s film career continued to thrive with Rollover (1981, with Jane Fonda), Flashpoint (1984), Big Top Pee Wee (1988), Welcome Home (1989), Knights (1993), Lone Star (1996) and Fire Down Below (1997). In 1998, he was cast in the vampire superhero action film Blade, which spawned two sequels. In the new millennium, Kristofferson took roles in Planet of the Apes (2001), Where the Red Fern Grows (2003), The Jacket (2005), Fast Food Nation (2006), He’s Just Not That Into You (2009, with Jennifer Anniston), Dolphin Tale (2011, plus a 2014 sequel) and Joyful Noise (2012, with Parton). He was also featured in a number of high-profile television films and miniseries. In 2015, he portrayed President Andrew Jackson in the historical miniseries Texas Rising.

His music continued to be prominent. “Help Me Make It Through the Night” was a soul-music hit three times—for Joe Simon, O.C. Smith and Gladys Knight—and his songs were also recorded by Black music stars Al Green, Tina Turner, Millie Jackson, Sammy Davis Jr. and Lena Horne. Such diverse artists as Elvis Presley, Dean Martin, Olivia Newton-John, Joan Baez, Tom Jones, Pattti Page, The Grateful Dead, Frank Sinatra and Carly Simon recorded Kristofferson songs, as did a who’s-who of country celebrities—Loretta Lynn, Glen Campbell, Emmylou Harris, George Jones, Tanya Tucker, Rosanne Cash, K.T. Oslin, Charley Pride, Dolly Parton, Anne Murray, Hank Snow, Dottie West, LeAnn Rimes, Merle Haggard, Charlie McCoy, Lynn Anderson, Roy Clark, Conway Twitty, Kenny Rogers, etc.

Career accolades rolled in. Kris Kristofferson was voted into the Nashville Songwriters Hall of Fame in 1977. The national Songwriters Hall of Fame followed suit in 1985. Induction into the Country Music Hall of Fame came in 2004.

The new Americana music genre coalesced in 1999-2000. This reinvigorated his recording career and brought him new honors. In 2003, he received the “Spirit of Americana” free-speech award from the Americana Music Association. In 2006, he issued This Old Road, his first album of new material in 11 years. It was succeeded by more Americana-music favorites, his Closer to the Bone (2009), Feeling Mortal (2013) and Cedar Creek Sessions (2016) albums. They demonstrated that he was still writing as powerfully as ever. He was also the subject of a tribute album 2006’s The Pilgrim.

In the fall of 2009, Kristofferson was celebrated as a BMI Icon. By then, his songwriting had earned him 48 BMI awards. In 2013 he won a Poet’s Award from the ACM. He was given a Grammy Lifetime Achievement Award in 2014. An all-star concert in Nashville celebrated his 80th birthday in 2016, and he appeared at the Newport Folk Festival that year. The CMA presented him with its Lifetime Achievement honor in 2019.

Kristofferson announced his retirement in January 2021. He had been experiencing memory loss for several years, possibly as a result of old head injuries from sports. He assigned his estate management to Morris-Higham Management in Nashville. In October 2023 he attended the Country Music Hall of Fame’s annual induction ceremony. This was his final public appearance.

Kris Kristofferson is survived by his wife Lisa and by eight children—Tracy, Kris Jr., Casey, Jesse, Jody, John Robert, Kelly Marie and Blake—as well as by seven grandchildren.

Funeral arrangements have not been announced.