# Kris Kristofferson

Kristoffer Kristofferson (June 22, 1936 – September 28, 2024) was an American singer, songwriter, and actor. He was a pioneering figure in the outlaw country movement of the 1970s, moving away from the polished Nashville sound and toward a more raw, introspective style. Some of his most famous songs include "Me and Bobby McGee", "For the Good Times", "Sunday Mornin' Comin' Down", and "Help Me Make It Through the Night", all of which became hits for other artists.
Kristofferson was born in Brownsville, Texas; the family relocated to San Mateo, California during his childhood and he was briefly drafted into military service in the early 1960s. After one single for Epic Records, Kristofferson was signed by Monument Records in 1969. Throughout his career, he recorded a total of 10 albums for Monument, two albums for Mercury Records, one album each for Justice Records and Atlantic Records, and two albums each for New West Records and KK Records. In September 1971, Kristofferson made his film debut in The Last Movie and devoted much of the later decade to making Hollywood films. Some of his most famous films include Cisco Pike (1972), A Star Is Born (1976), Heaven's Gate (1980), and the Blade film trilogy (1998–2004).
Kristofferson was also a member of the country music supergroup the Highwaymen between 1985 and 1995. He has charted 12 times on the American Billboard Hot Country Songs charts; his highest peaking singles there are "Why Me" and "Highwayman", which reached number one in 1973 and 1985, respectively. He was inducted into the Country Music Hall of Fame in 2004 and received the Grammy Lifetime Achievement Award in 2014. He was a three-time Grammy Award winner, out of 13 total nominations.

## Life and career
### 1936–1965: early years and military service

Kristoffer Kristofferson was born in Brownsville, Texas, the oldest of three children born to Mary Ann (née Ashbrook) and Henry Kristofferson, a United States Army Air Corps officer (later a major general in the United States Air Force). Henry later worked as a manager for Saudi Aramco after retiring from the service. During Kristofferson's childhood, his father encouraged him to pursue a military career.
Kristofferson moved around frequently as a youth because of his father's military service, and the family settled in San Mateo, California. He attended San Mateo High School, where he graduated in 1954. At age 17, Kristofferson took a summer job with a dredging contractor on Wake Island in the western Pacific Ocean. He called it "the hardest job I ever had".
Kristofferson went to Pomona College in Pomona, California, as a literature major. He studied under Frederick Sontag, whom he considers an important influence in his life. His early writing included prize-winning essays: "The Rock" and "Gone Are the Days" were published in The Atlantic Monthly. These stories touch on the roots of Kristofferson's passions and concerns. "The Rock" is about a geographical feature resembling the form of a woman, while the latter was about a racial incident. During this time, Kristofferson worked in various construction jobs and as a firefighter. He appeared in the March 31, 1958, issue of Sports Illustrated for his achievements in collegiate rugby union, American football, and track and field. He and his classmates also revived the Claremont Colleges Rugby Club, and it remains a Southern California rugby institution. Kristofferson graduated in 1958, earning a Bachelor of Arts degree, summa cum laude, in literature. He was elected to Phi Beta Kappa his junior year.
Also in 1958, Kristofferson was awarded a Rhodes Scholarship to the University of Oxford in Oxford, England, studying at Merton College. While performing his own songs there, Kristofferson signed with Larry Parnes, best known for his work with Tommy Steele. Parnes was working to sell Kristofferson as "a Yank at Oxford" to the British public; Kristofferson was willing to accept that promotional approach if it helped his singing career, which he hoped would enable him to progress toward his goal of becoming a novelist. He recorded for The Rank Organisation's Top Rank Records label as Kris Carson, but this early phase was unsuccessful. In 1960, Kristofferson graduated with a B.Phil. in English literature.
In 1961, he married his longtime girlfriend, Frances "Fran" Mavia Beer. Also in 1961, Kristofferson joined the United States Army and was commissioned as a second lieutenant, eventually the rank of captain. He relocated Beer and their newborn daughter to West Germany, where he served as a member of the 8th Infantry Division. During this period, Kristofferson resumed his music career and formed a band to play at service clubs. It was at this point that he met Marijohn Wilkin, the aunt of his platoon commander. In 1965, after his tour in West Germany ended, Kristofferson briefly taught English literature at the United States Military Academy in West Point, New York.

### 1965–1972: early music and film career

In June 1965, while on a two-week leave from West Point, he contacted Wilkin in Nashville, Tennessee, and decided to become a country music songwriter. After resigning from the Army and relocating his family to Nashville that year, Wilkin signed Kristofferson to her publishing house Buckhorn Music. Wilkin pitched his song "Talkin' Vietnam Blues" to singer Dave Dudley. Concurrently, Kristofferson held various jobs including as a bartender, a construction worker, and a railroad worker. He later worked as a janitor for Columbia Records, which afforded him the possibility of talking directly with the artists and a presence during recording sessions. He released his debut single containing his songs "Golden Idol" and "Killing Time" in 1967 on Epic Records.
After his second child was born with esophagus issues in 1968, Kristofferson worked at Petroleum Helicopters International (PHI) in Lafayette, Louisiana. While flying workers to and from oil rigs in the Gulf of Mexico, he would often write new songs. At weekends, he returned to Nashville, and for the following week he would pitch the songs around town before returning to Louisiana. The trips exhausted Kristofferson; his children were living with Fran in California and he felt his career as a songwriter was failing. PHI also admonished him for his increased alcohol consumption. Upon returning to Nashville the same week, Kristofferson learned three of his songs had been recorded: "Jody and the Kid" by Roy Drusky, "Help Me Make It Through the Night" by Jerry Lee Lewis and "Me and Bobby McGee" by Roger Miller.
Through June Carter, Kristofferson first attempted to pitch material to her husband Johnny Cash. Carter took the demos, which were eventually lost in a pile of other material Cash had received. At the time, Kristofferson worked on the weekends for the Tennessee National Guard. To attract Cash's attention, Kristofferson landed a helicopter in Cash's property. Cash eventually invited Kristofferson to a "guitar pull" party in his house. Cash was impressed and invited Kristofferson to perform with him at the 1969 Newport Folk Festival. Unsatisfied by Buckhorn Music, Kristofferson decided to change labels. Monument Records director Bob Beckham invited Kristofferson to play songs for him and label owner Fred Foster. Kristofferson performed "To Beat the Devil", "Jody and the Kid", "The Best of All Possible Worlds" and "Duvalier's Dream"; Foster was impressed and signed Kristofferson to Monument as a recording artist and Combine Music as a songwriter. The ten-year contract required Kristofferson to submit ten records containing songs he had written. Kristofferson was surprised he had been signed as a singer; he told Foster at the time: "I can't sing, I sound like a frog!" Kristofferson later said Buckhorn Music had not allowed him to record demos of his compositions.
In 1969, Kristofferson divorced Beer and left Nashville to join the production of his first motion picture, Dennis Hopper's The Last Movie, in Peru. In his absence, Cash continued promoting Kristofferson's original songs with other singers. Upon returning to Nashville, Kristofferson learned of his new popularity and started to work on his debut album for Monument, Kristofferson. As his manager and producer, Foster had decided to keep some of Kristofferson's original material from being passed to other artists. The new material, as well as his songs that had already been recorded by other artists, were included in the recording sessions, which were held at Monument Recording Studio.
Monument released Kristofferson in June 1970. Kristofferson wrote or co-wrote every song on the album. He collaborated with Marijohn's son, John Buck Wilkin, on "Blame it on the Stones". Though Kristofferson was not a commercial success, it received positive reviews from critics. According to Robert Hilburn of the Los Angeles Times, the album "is able to combine lyric sophistication with country music's traditional interest in everyday problems". The commercial success of "Sunday Mornin' Comin' Down" led to the first of several industry awards nominations for the singer. Johnny Cash's rendition of the single earned Kristofferson his first Country Music Association award for Song of the Year that November.
Also in 1970, he made his debut performance as a singer at the Los Angeles nightclub The Troubadour. Fred Roos, the casting director of Bob Rafelson's Five Easy Pieces, invited him to audition for his film debut for a leading role on Two-Lane Blacktop. Kristofferson, who was signed to Columbia Records, arrived to the appointment intoxicated and left. Kristofferson was next offered Bill L. Norton's script for Cisco Pike by Columbia. His peers encouraged him to reject the role and to take acting lessons instead, but he accepted the part, and later said; "I read the script and I could identify with this cat" and that acting is "understanding a character, and then being just as honest as you can possibly be".
Kristofferson began an 18-month tour, during which he suffered a bout of walking pneumonia, which was worsened by his alcohol consumption. While performing, he would not face the audience and mumbled the words to his songs. Eventually, he was hospitalized. During the tour, Kristofferson performed on The Johnny Cash Show. While in California, Kristofferson befriended singer Janis Joplin. Upon returning to Nashville in early 1971, he received with his mail at Combine Music Joplin's posthumous album Pearl, which at the time was still unreleased. Joplin's album included a cover of his original composition "Me and Bobby McGee". The following morning, he returned to the studio and recorded his second Monument album, The Silver Tongued Devil and I, which was released that July. He wrote nine of the album's 10 songs, including the single "Lovin' Her Was Easier (than Anything I'll Ever Do Again)". He collaborated with songwriter Shel Silverstein on "The Taker" and keyboardist Donnie Fritts on "Epitaph (Black and Blue)". Also included on the album was a cover of Bobby Bare's "Good Christian Soldier". "Lovin' Her Was Easier (than Anything I'll Ever Do Again)" reached number 46 on Billboard Hot 100 and number 4 on Adult Contemporary. These songs would later be used on the soundtrack for Cisco Pike, which was released on January 14, 1972.
That February, Monument released his third album Border Lord. The album was all-new material and sales were sluggish. He also swept the Grammy Awards that year with numerous songs nominated, winning country song of the year for "Help Me Make It Through the Night". Kristofferson's fourth album, Jesus Was a Capricorn, initially had slow sales, but the third single, "Why Me", was a success and significantly increased album sales. It sold over one million copies, and was awarded a gold disc by the RIAA on November 8, 1973. Kristofferson appeared with Rita Coolidge on the BBC television series The Old Grey Whistle Test, performing "Help Me Make It Through the Night". Al Green later released his version of "For the Good Times" on the album I'm Still in Love with You.

### 1973–1985: commercial peak

In April 1973, Kristofferson received an honorary doctorate in fine arts from Pomona College during Alumni Weekend, accompanied by Cash and Coolidge. Four months later, Kristofferson married Coolidge. The duo released an album titled Full Moon, another success buoyed by numerous hit singles and Grammy nominations.
His fifth album, Spooky Lady's Sideshow, released in 1974, was a commercial failure, setting the trend for most of the rest of his musical career. Artists such as Ronnie Milsap and Johnny Duncan continued to record Kristofferson's material with success, but his distinctively rough voice and anti-pop sound kept his own audience to a minimum. Meanwhile, more artists took his songs to the top of the charts, including Willie Nelson, whose 1979 LP release of (Willie Nelson) Sings Kristofferson reached number five on the U.S. Country Music chart and certified Platinum in the U.S.
In 1979, Kristofferson traveled to Havana, Cuba, to participate in the historic Havana Jam festival that took place on March 2–4, alongside Coolidge, Stephen Stills, the CBS Jazz All-Stars, the Trio of Doom, Fania All-Stars, Billy Swan, Bonnie Bramlett, Mike Finnigan, Weather Report, and Billy Joel, plus an array of Cuban artists such as Irakere, Pacho Alonso, Tata Güines, and Orquesta Aragón. His performance is captured on Ernesto Juan Castellanos's documentary Havana Jam '79.
On November 18, 1979, Kristofferson and Coolidge appeared on The Muppet Show, where Kristofferson sang "Help Me Make It Through the Night" with Miss Piggy, Coolidge sang "We're All Alone" with forest animals, and the pair sang "Song I'd Like to Sing" with the Muppet monsters. They divorced in 1980.
In 1982, Kristofferson joined Willie Nelson, Dolly Parton, and Brenda Lee on The Winning Hand, a double album consisting of remastered and updated performances of recordings the four artists had made for the Monument label during the mid-1960s; the album reached the top ten on the U.S. country album charts. He married again, to Lisa Meyers, and concentrated on films for a time, appearing in the 1984 releases The Lost Honor of Kathryn Beck, Flashpoint, and Songwriter. Nelson and Kristofferson both appeared in Songwriter, and Kristofferson was nominated for an Academy Award for Best Original Score. The album Music from Songwriter, featuring Nelson-Kristofferson duets, was a country success.

### 1985–2021: Highwaymen and later years

Nelson and Kristofferson continued their partnership, and by 1985, they added Waylon Jennings and Johnny Cash to form the supergroup the Highwaymen. Their self-titled first album, released on May 6, was a success, and the supergroup continued working together for a time. The single from the album, a cover of Jimmy Webb's "Highwayman", was awarded the ACM's single of the year in 1985. In 1985, Kristofferson starred in Trouble in Mind and released Repossessed, a politically aware album that was a country success, particularly "They Killed Him" (also performed by Bob Dylan), a tribute to his heroes, including Martin Luther King Jr., Jesus, and Mahatma Gandhi. Kristofferson also appeared in Amerika at about the same time, a miniseries that attempted to depict life in America under Soviet control.
In spite of the success of Highwayman 2 in 1990, Kristofferson's solo recording career slipped significantly in the early 1990s, though he continued to record successfully with the Highwaymen. Lone Star (1996 film by John Sayles) reinvigorated Kristofferson's acting career, and he soon appeared in Blade, Blade II, Blade: Trinity, A Soldier's Daughter Never Cries, Fire Down Below, Tim Burton's remake of Planet of the Apes, Chelsea Walls, Payback, The Jacket, and Fast Food Nation.
The Songwriters Hall of Fame inducted Kristofferson in 1985, as had the Nashville Songwriters Hall of Fame earlier, in 1977. In 1999, The Austin Sessions was released, an album on which Kristofferson reworked some of his favorite songs with the help of artists such as Mark Knopfler, Steve Earle, and Jackson Browne. Shortly after the album's release, he underwent coronary artery bypass surgery.
In 1997, Kristofferson co-starred in the film Fire Down Below with Steven Seagal. Kristofferson appeared in the Stephen Norrington film Blade, alongside Wesley Snipes, as Blade's mentor Abraham Whistler. He reprised the role in Blade II (2002) and again in Blade: Trinity (2004). In 1998 he starred in Dance with Me along with Vanessa Williams and Chayanne.
In 2003, Broken Freedom Song was released, a live album recorded in San Francisco. That year, he received the "Spirit of Americana" free speech award from the Americana Music Association. In 2004, he was inducted into the Country Music Hall of Fame. On October 21, 2005, the movie Dreamer was released, in which Kristofferson played the role of "Pop", a retired thoroughbred horse trainer. The movie was inspired by the true story of the mare Mariah's Storm which won the Turfway Breeders Cup Classic. In 2006, he received the Johnny Mercer Award from the Songwriters Hall of Fame and released his first album full of new material in 11 years; This Old Road. On April 21, 2007, Kristofferson won CMT's Johnny Cash Visionary Award. Rosanne Cash, Cash's daughter, presented the honor during the April 16 awards show in Nashville. Previous recipients include Cash, Hank Williams Jr., Loretta Lynn, Reba McEntire, and the Dixie Chicks. "John was my hero before he was my friend, and anything with his name on it is really an honor in my eyes," Kristofferson said during a phone interview. "I was thinking back to when I first met him, and if I ever thought that I'd be getting an award with his name on it, it would have carried me through a lot of hard times." In 2006, Kristofferson starred with Geneviève Bujold in the film Disappearances about whiskey running from Quebec to the U.S. during the Great Depression.
In July 2007, Kristofferson was featured on CMT's Studio 330 Sessions where he played many of his hits.
On June 13, 2008, Kristofferson performed an acoustic in-the-round set with Patty Griffin and Randy Owen (Alabama) for a special taping of a PBS songwriters series aired in December. Each performer played five songs. Kristofferson's set included "The Best of All Possible Worlds", "Darby's Castle", "Casey's Last Ride", "Me and Bobby McGee", and "Here Comes that Rainbow Again". Taping was done in Nashville.
Kristofferson released a new album of original songs titled Closer to the Bone on September 28, 2009. It is produced by Don Was on the New West Records label. Prior to the release, Kristofferson remarked: "I like the intimacy of the new album. It has a general mood of reflecting on where we all are at this time of life."
On November 10, 2009, Kristofferson was honored as a BMI Icon at the 57th annual BMI Country Awards. Throughout his career, Kristofferson's songwriting garnered 48 BMI Country and Pop Awards. He later remarked, "The great thing about being a songwriter is you can hear your baby interpreted by so many people that have creative talents vocally that I don't have." Kristofferson had always denied having a good voice, and had said that as he had aged, any quality it once had was beginning to decay.
In December 2009, it was announced that Kristofferson would be portraying Joe on the upcoming album Ghost Brothers of Darkland County, a collaboration between rock singer John Mellencamp and novelist Stephen King.
On May 11, 2010, Light in the Attic Records released demos that were recorded during Kristofferson's janitorial stint at Columbia. Please Don't Tell Me How the Story Ends: The Publishing Demos was the first time these recordings were released and included material that would later be featured on other Kristofferson recordings and on the recordings of other prominent artists, such as the original recording of "Me and Bobby McGee".
On June 4, 2011, Kristofferson performed a solo acoustic show at the Maui Arts and Cultural Center, showcasing both some of his original hits made famous by other artists, and newer songs.
In early 2013, Kristofferson released a new album of original songs called Feeling Mortal. A live album titled An Evening With Kris Kristofferson was released in September 2014.
Kristofferson voiced the character Chief Hanlon of the NCR Rangers in the hit 2010 video game Fallout: New Vegas.
In an interview for Las Vegas magazine Q&A by Matt Kelemen on October 23, 2015, Kristofferson revealed that a new album, The Cedar Creek Sessions, recorded in Austin, would include some old and some new songs. Released on June 17, 2016, it would be his last studio album issued during his lifetime. That December, the album was nominated for a Grammy Award for Best Americana Album.
Kristofferson covered Brandi Carlile's "Turpentine" on the 2017 album Cover Stories.
In August 2018, Kristofferson's final film, Blaze, opened. Three months later, on November 7, Kristofferson performed, with assistance from Carlile, the Joni Mitchell composition "A Case of You", from the 1971 Mitchell album Blue, at the Both Sides Now – Joni 75 A Birthday Celebration to celebrate the 75th birthday of Mitchell.
In June 2019, Kristofferson was announced as being one of the supporting artists for a Barbra Streisand "exclusive European concert" on July 7 in London's Hyde Park as part of the Barclay's Summertime Concert series.

### 2021–2024: Retirement and death

By January 2021, Kristofferson announced his retirement from performing, citing age and concerns regarding the COVID-19 pandemic. According to manager Tamara Saviano, "It was an evolution, and it just felt very organic." Kristofferson's final performance was held in Los Angeles at the Hollywood Bowl on April 29, 2023, where he sang a cover of "Lovin' You Was Easier" with Rosanne Cash in honor of Willie Nelson's 90th birthday; the concert was later released as Long Story Short: Willie Nelson 90 that December.
On September 28, 2024, Kristofferson died at his home in Hana, Hawaii, at the age of 88. He previously requested for the first three lines of Leonard Cohen's "Bird on the Wire" on his tombstone:
   Like a bird on the wire Like a drunk in a midnight choir I have tried in my way to be free

## Personal life

In 1961, Kristofferson married his longtime girlfriend Frances "Fran" Mavia Beer, but they divorced in 1969. Kristofferson briefly dated Janis Joplin before her death in October 1970. His second marriage was to singer Rita Coolidge in 1973, ending in divorce in 1980. Kristofferson married Lisa Meyers in 1983.
Kristofferson and Meyers owned a home in Las Flores Canyon in Malibu, California, and they also resided in Hana, Hawaii from 1990 until his death. Kristofferson had eight children from his three marriages: two from his first marriage, one from his second marriage, and five from his marriage to his third wife.

### Political views and advocacy

Kristofferson was a vocal opponent of the Gulf War and Iraq War and a critic of a number of United States military interventions and foreign policy positions, including the United States invasion of Panama and U.S. support of the Contras during the Nicaraguan Revolution and of the Apartheid government in South Africa.
Kristofferson endorsed Jesse Jackson's presidential campaign in 1988 and Ross Perot's presidential campaign in 1992.
Kristofferson's debut LP included a pro-Vietnam War song, but he said that he later became an opponent of the war after speaking with returning soldiers who had seen combat. Speaking about a soldier who had told him that he had witnessed other soldiers throwing people out of helicopters during interrogation, Kristofferson said, "The notion that you could make a young person do something so inhumane to another soldier—or even worse, a civilian—convinced me that we were in the wrong." Kristofferson called himself a "dove with claws" and remained proud of his military service in spite of his anti-imperialist views.
In a 1991 interview on New Zealand TV, he condemned media support for the Gulf War, saying "The lapdog media cranks out propaganda that would make a Nazi blush." Kristofferson was a supporter of the United Farm Workers and appeared at several rallies and benefits for them, campaigning with Cesar Chavez for the passage of Proposition 14. He continued to play at benefits for the UFW through the 2010s. In 1987, he played at a benefit concert for Leonard Peltier with Jackson Browne, Willie Nelson and Joni Mitchell. In 1995, he dedicated a song to Mumia Abu-Jamal at a concert in Philadelphia, and was booed by the crowd.
He performed in benefit concerts for Palestinian children, and said that he "found a considerable lack of work as a result." At a Bob Dylan anniversary concert shortly after Sinead O'Connor's protest on Saturday Night Live, he showed solidarity with her when she was booed by the crowd.

## Discography
### Studio albums

* Kristofferson (1970)
* The Silver Tongued Devil and I (1971)
* Border Lord (1972)
* Jesus Was a Capricorn (1972)
* Full Moon (with Rita Coolidge) (1973)
* Spooky Lady's Sideshow (1974)
* Breakaway (with Rita Coolidge) (1974)
* Who's to Bless and Who's to Blame (1975)
* Surreal Thing (1976)
* Easter Island (1978)
* Natural Act (with Rita Coolidge) (1978)
* Shake Hands with the Devil (1979)
* To the Bone (1981)
* Repossessed (1986)
* Third World Warrior (1990)
* A Moment of Forever (1995)
* The Austin Sessions (1999)
* This Old Road (2006)
* Closer to the Bone (2009)
* Feeling Mortal (2013)
* The Cedar Creek Sessions (2016)

## Filmography
### Films starred

* 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)
* Convoy (1978)
* Heaven's Gate (1980)
* Flashpoint (1984)
* Big Top Pee-wee (1988)
* Lone Star (1996)
* Blade (1998)
* Molokai: The Story of Father Damien (1999)
* Blade II (2002)
* Blade: Trinity (2004)
* Dolphin Tale (2011)

## Awards and nominations

| Year | Association | Category | Nominated work | Result |
| 1970 | Country Music Association Awards | Song of the Year | "Sunday Mornin' Comin' Down" | Won |
| 1973 | Country Music Association Awards | Song of the Year | "Why Me" | Nominated |
| 1973 | Country Music Association Awards | Single of the Year | "Why Me" | Nominated |
| 1973 | Academy of Country Music Awards | Song of the Year | "Why Me" | Nominated |
| 1973 | BAFTA Awards | Best Newcomer | Pat Garrett and Billy the Kid | Nominated |
| 1974 | Academy of Country Music Awards | Song of the Year | "One Day at a Time" | Nominated |
| 1976 | Golden Globe Awards | Best Actor in a Musical | A Star Is Born | Won |
| 1984 | Academy Awards | Best Original Score | Songwriter | Nominated |
| 1985 | Country Music Association Awards | Single of the Year | "Highwayman" | Nominated |
| 1985 | Country Music Association Awards | Video of the Year | "Highwayman" | Nominated |
| 1985 | Academy of Country Music Awards | Single of the Year | "Highwayman" | Won |
| 1985 | Academy of Country Music Awards | Video of the Year | "Highwayman" | Nominated |
| 1985 | Academy of Country Music Awards | Album of the Year | "Highwayman" | Nominated |
| 2003 | Americana Music Honors & Awards | Free Speech Award | Himself | Won |
| 2005 | Academy of Country Music Awards | Cliffie Stone Pioneer Award | Himself | Won |
| 2013 | Academy of Country Music Awards | Poets Award | Himself | Won |
| 2019 | Country Music Association Awards | Lifetime Achievement Award | Himself | Won |

### Grammy Awards

Kristofferson has won three competitive Grammys from thirteen nominations. He received the Lifetime Achievement Award in 2014.
| Year | Category | Nominated work | Result |
| 1971 | Song of the Year | "Me and Bobby McGee" | Nominated |
| 1971 | Song of the Year | "Help Me Make It Through the Night" | Nominated |
| 1971 | Best Country Song | "Help Me Make It Through the Night" | Won |
| 1971 | Best Country Song | "Me and Bobby McGee" | Nominated |
| 1971 | Best Country Song | "For the Good Times" | Nominated |
| 1973 | Best Country Song | "Why Me" | Nominated |
| 1973 | Best Male Country Vocal Performance | "Why Me" | Nominated |
| 1973 | Best Country Performance by a Duo or Group | "From The Bottle To The Bottom" (with Rita Coolidge) | Won |
| 1974 | Best Country Performance by a Duo or Group | "Loving Arms" (with Rita Coolidge) | Nominated |
| 1975 | Best Country Performance by a Duo or Group | "Lover Please" (with Rita Coolidge) | Won |
| 1985 | Best Country Performance by a Duo or Group | "Highwayman" (with the Highwaymen) | Nominated |
| 1990 | Grammy Award for Best Country Collaboration with Vocals | Highwayman 2 | Nominated |
| 2014 | Grammy Lifetime Achievement Award | Himself | Won |
| 2016 | Best Americana Album | The Cedar Creek Sessions | Nominated |