American Masters (2016 Season) — The Highwaymen: Friends Till the End

Group Bio & Timeline

Air date: 05/27/2016

American Masters – The Highwaymen: Friends Till the End

Premieres nationwide Friday, May 27 at 9:00 p.m. ET on PBS (check local listings)


The Highwaymen Biography & Timeline

The Highwaymen — Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson — were country music’s first bonafide supergroup, an epic quartet of blockbuster star power comprised of the four prime forces of America’s outlaw country music revolution. An essential musical and cultural influence, The Highwaymen were active for the decade spanning 1985 – 1995, recorded three major label albums, charted hit singles (including their No. 1 debut, “Highwayman,” which won the Best Country Song Grammy Award in 1986) and performed a variety of shows, achieving mythic status for those lucky enough to have been there.

“There’s the four of us standing there, grouped around microphones. The Highwaymen. John, Kris, Willie, and me. I don’t think there are any other four people like us,” wrote Waylon Jennings in Waylon: An Autobiography. “John says that we came together because we all have a life commitment to the music. We know the same songs, but we sing them from different perspectives. We can blend the early country of the Carter Family with Texas swing, southern gospel, and rockabilly, and each of us feels comfortable singing real slices of life. There’s not one of us who hasn’t come face to face with his own mortality, and many’s the time we’ve gone through our struggles and survivals together….That’s our friendship, unlocking any door that stands between us, and it keeps four very different individuals together.”



Johnny Cash is born John R. Cash on February 26 in Kingsland, Arkansas.


Willie Nelson is born April 29 in Abbott, Texas. His mother and father leave him and his sister to be raised by Willie’s grandparents.


Kristoffer (Kris) Kristofferson is born on June 22 in Brownsville, Texas. His father was a U.S. Army Air Corps officer, and he grew up a “military brat” until his family finally settled in San Mateo, California.


Waylon Jennings is born June 15 in Littlefield, Texas.


Willie Nelson’s grandfather gives him his first guitar.


Willie Nelson writes his first song.


Johnny Cash begins playing and writing songs. Cash’s older brother Jack dies after a sawmill accident. Johnny feels tremendous guilt over his older brother’s death for the rest of his life.


Willie Nelson begins singing at venues around Abbott to earn so money so he won’t have to partake in cotton farming.


Willie Nelson leaves high school and serves in the U.S. Air Force for less than a year.

On July 7th, Johnny Cash enlists in the U.S. Air Force and is assigned to a base in West Germany working on radio intercepts.


Willie Nelson marries Martha Matthews and has three children.


Waylon Jennings drops out of high school and works odd jobs, including as a truck driver and in his father’s produce store. During this period, he meets Buddy Holly for the first time.


Kris Kristofferson graduates high school and enrolls in Pomona College in Southern California, intent on becoming a writer. He also excels as an athlete in sports such as rugby and football.

Willie Nelson attends Baylor University in Waco, Texas.

Johnny Cash is honorably discharged from the U.S. Air Force on July 3. One month later, he marries Vivian Liberto. They had dated since 1951 when she was 17 years old and he was 19 years old. They have four daughters together.


John R. Cash signs with Sun Records in Memphis, Tennessee, and he adopts the name Johnny Cash. Among the first of many songs he records is “Folsom Prison Blues,” as well as “Hey Porter” and “Cry, Cry, Cry”.


Johnny Cash’s song “I Walk the Line” becomes the No. 1 Hot Country Single.

On December 4th, Johnny Cash, Carl Perkins, Jerry Lee Lewis, and Elvis Presley record an impromptu jam session called the Million Dollar Quartet that was a rare intersection of the careers of four artists who profoundly changed American music.

Willie Nelson leaves Baylor University to focus on his music.

Waylon Jennings moves to Lubbock, Texas, and works as a radio DJ. He is eventually fired for continuing to play the music of artists such as Little Richard and Chuck Berry. He also marries Maxine Lawrence, and they have four children.


Kris Kristofferson graduates summa cum laude from Pomona College with a degree in literature and becomes a Rhodes Scholar at Oxford University. He excels at boxing and begins dabbling in songwriting while still intent on becoming a writer.


Waylon Jennings is hired to play bass for Buddy Holly’s band.

On the night of February 2nd, after several problems with their tour bus, Buddy Holly chartered a plane to fly himself and some other musicians from Iowa to their next gig in Fargo, North Dakota. Jennings decides to take the bus and tells Holly, “I hope your ol’ plane crashes.” Soon after takeoff, the plane carrying Buddy Holly, Ritchie Valens, The Big Bopper, and the pilot crashes in an Iowa cornfield – they all are killed. Their deaths would haunt Jennings for the rest of his life.


Kris Kristofferson graduates from Oxford University with a master’s degree in English literature. Soon after, he joins the U.S. Army, completes Ranger school, and becomes a helicopter pilot. He eventually attains the rank of captain.

Willie Nelson moves to Nashville, Tennessee, and soon joins Ray Price’s band as a bassist.


Kris Kristofferson marries his longtime girlfriend Frances Beer. They have two children together.


Willie Nelson’s first album, …And Then I Wrote, is released.

Waylon Jennings marries Lynne Mitchell. They have one child together.


Johnny Cash’s cover of “Ring of Fire” (written by June Carter and Merle Kilgore) becomes a No. 1 hit on the Hot Country Singles chart.


Waylon Jennings releases his first album, Waylon at JD’s.


Kris Kristofferson meets Johnny Cash backstage at the Grand Ole Opry in Nashville, Tennessee, while on leave from the Army. Kristofferson said Cash, “looked like a panther. And he was messed up as he often was in those days. He was skinny as a snake, but he had an electricity about him…” Kristofferson soon left the Army (even turning down an opportunity to teach English at the U.S. Military Academy), moved to Nashville, and worked as a janitor and helicopter pilot, while writing songs for other artists to perform.

Around this time, Waylon Jennings also moved to Nashville and, for a time, was roommates with Johnny Cash.


Waylon Jennings releases his first major label album from RCA Records, called Folk-Country.


Waylon Jennings marries Barbara Rood.


Johnny Cash’s live album, At Folsom Prison, includes a new recording of “Folsom Prison Blues” that shoots to the top of the Hot Country charts and earns Cash a Grammy for Best Country Vocal Male Performance.

Cash proposes to singer/songwriter June Carter live on stage during a concert in London, Ontario, Canada, 13 years after they first met. Soon after, they marry. Two years later, they have their only child, John Carter Cash.


The song “Me and Bobby McGee” is written by Kris Kristofferson.

Waylon Jennings marries Jessi Colter. They have one son together, Shooter Jennings. They remain married until Waylon’s death in 2002.

The Johnny Cash Show debuts on ABC. The musical variety show features musical guests such as Bob Dylan, Waylon Jennings, Kris Kristofferson, and Linda Ronstadt.

While Bob Dylan is in Nashville recording his album Nashville Skyline, he and Johnny Cash have their only recording session together, which includes a duet of “Girl From the North Country.” They are both big fans of each other’s work.


Kris Kristofferson’s debut album, Kristofferson, is released.

Johnny Cash first records and performs Kristofferson’s song “Sunday Morning Coming Down” and chooses to sing it on TV.


Janis Joplin’s version of Kris Kristofferson’s song “Me and Bobby McGee” tops the U.S. Singles chart and becomes a No. 1 hit single after Janis’ death in 1971.

Kristofferson’s second album, The Silver Tongued Devil and I, is released to great success. Kristofferson’s debut album is also re-released and retitled Me and Bobby McGee after Joplin’s successful cover of the song. Both albums are certified Gold (500,000 copies sold).

The Johnny Cash Show ends its run on ABC.


The outlaw country movement starts to pick up momentum and is embodied in musicians such as Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash. The genesis of the movement lies in the frustration with the constraints put on musicians by record labels, producers, and publishers from Nashville.

Willie Nelson becomes frustrated by the Nashville music scene, as well as its establishment, and moves to Austin, Texas. He encounters a new, youth rock-based audience (from the University of Texas at Austin) mixed with a traditional country audience. “There were long-haired cowboys and short-haired cowboys, and the air smelled different…I noted that everyone was getting along.” He also encouraged Waylon Jennings to come perform in Austin.


Willie Nelson’s first annual 4th of July picnic/concert occurs in Dripping Springs, Texas. Waylon Jennings and Kris Kristofferson are among the performers. Like a Texas version of Woodstock, the event draws an assortment of hippies and rockers in addition to the traditional country fans. The event is a success with about 40,000 people attending.

Kris Kristofferson marries singer/songwriter Rita Coolidge. They have one daughter together.


Waylon Jennings’ album This Time, produced by Jennings and Willie Nelson, is released. The album epitomizes the outlaw country movement, because when Waylon first gave the album to the record company they said, “This is wonderful. Now we have to go in the studio and cut it.” And Waylon said, “No, that’s all you got.” It went on to be a hit, and the album that the record company had wanted to change peaked at No. 4 on the Billboard chart.


Willie Nelson’s album Red Headed Stranger is released. During the recording he had unprecedented creative freedom, using his touring band.

Waylon Jennings’ 22nd studio album, Dreaming My Dreams, is released. Two years later it’s certified Gold (500,000 copies sold).


Waylon Jennings, Willie Nelson, Jessi Colter, and Tompall Glaser record the hit, bestselling album Wanted! The Outlaws. It is the first country album to go Platinum and sell 1 million copies (in 1985 the album went Double Platinum). The album also continues to define and popularize the genre of outlaw country music. Jennings said in his autobiography, “For us, ‘outlaw’ meant standing up for your rights, your own way of doing things. It felt like a different music, and outlaw was as good a description as any.”

Kris Kristofferson’s stars with Barbra Streisand in the hit movie A Star is Born. The soundtrack eventually becomes a big seller with over 4 million copies sold by 1984. Over the years Kristofferson stars in a number of major films such as Lone Star, Blade and A Soldier’s Daughter Never Cries.


Waylon Jennings and Willie Nelson release the album Waylon & Willie, which includes a cover of “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” In 1985, the album attains Double Platinum status (over 2 million copies sold).


Waylon Jennings writes and records the theme song for the hit TV series The Dukes of Hazzard. Jennings also narrates each episode.


Willie Nelson’s album Somewhere Over the Rainbow, a collection of covers of hit songs from the 1930s and 40s, shoots to the top of the Country charts. That same year, the album is certified Platinum (over 1 million copies sold).


Kris Kristofferson marries Lisa Meyers, an attorney. They have five children together and are married currently.


The Highwaymen come together. Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson go to Switzerland to record a television Christmas special. They enjoy working together and decide to collaborate on a record produced by Chips Moman.

During the recording, Marty Stuart (a member of Johnny Cash’s backing band, as well as his then son-in-law) plays the song “Highwayman” by Jimmy Webb for Johnny Cash and Chips Moman. The song has four distinct parts and defined the group. It soon becomes a hit and the group adopts the name, The Highwaymen, for their country music supergroup.

On August 17th, “Highwayman” soars to No. 1 on Billboard’s Hot Country Songs chart.

“Highwayman” wins the Grammy for Best Country Song.


Capitalizing on their success, The Highwaymen star in the CBS-TV movie Stagecoach, a remake of the 1939 John Wayne/John Ford classic western.

On February 10th, the album The Highwaymen is Gold certified with over 500,000 copies sold (it goes Platinum in 2000).


A folk group named The Highwaymen, who had a hit with the song “Michael” (a cover of “Michael, Row the Boat Ashore”) in 1961, sues the country music supergroup for using their name. The frivolous lawsuit is dropped after the folk group is allowed to open a concert for the supergroup The Highwaymen.

The Highwaymen release their second studio album, Highwayman 2. It reaches No. 4 on the Country charts.


Willie Nelson marries Annie D’Angelo, a make-up artist he met on the set of Stagecoach. They are married currently.


The Highwaymen perform at Farm Aid in Irving, Texas.


The Highwaymen perform at Farm Aid for the second time in Ames, Iowa.


Gene Autry (“The Singing Cowboy”) pays The Highwaymen a visit during the recording of their third studio album. Autry is a famous radio, TV and film performer, as well as one of the most important country music stars of the 20th century. The Highwaymen consider Autry one of their heroes.


The third and final studio album from The Highwaymen, The Road Goes on Forever, is released.


After suffering for years with diabetes-related health problems, Waylon Jennings dies on February 13 in Chandler, Arizona.

Johnny Cash collaborates with acclaimed record producer Rick Rubin (co-founder of Def Jam Records) on the album American IV: The Man Comes Around. Cash’s cover of the Nine Inch Nails song “Hurt” receives critical and popular acclaim. The music video is considered to be one of the greatest of all time.


Johnny Cash dies on September 12 in Nashville, Tennessee. Four months earlier, his wife June Carter Cash died.


At Johnny Cash’s 80th birthday bash in Austin, Texas, Willie Nelson and Kris Kristofferson reunite and perform “Highwayman,” accompanied by Jamey Johnson and Waylon Jennings’ son Shooter Jennings.


Willie Nelson and Kris Kristofferson reunite and perform “Highwayman” at the Grammy Awards, accompanied by Merle Haggard and Blake Shelton.


Willie Nelson and Kris Kristofferson reunite in Austin, Texas, for a tribute to Waylon Jennings that also features Jamey Johnson, Toby Keith, Lee Ann Womack, and Jennings’ widow Jessi Colter. Willie and Kris also perform “Highwayman” with Jamey Johnson and Waylon’s son Shooter Jennings.