Complete List Of The Highwaymen Albums And Songs

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The Highwaymen were a country music supergroup comprised of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson—four pioneers of the outlaw country movement. Formed in 1985, they became known for their rebellious spirit, blending their unique styles to create a powerful sound that transcended the traditional Nashville scene. Their debut album Highwayman produced the number one hit “Highwayman,” solidifying their place in music history. Over the next decade, they released two more studio albums, including Highwayman 2 and The Road Goes on Forever, both of which continued to showcase their enduring artistry and chemistry as a group. Their catalog later expanded with the two-CD compilation The Essential Highwaymen in 2010 and the archival live set The Highwaymen Live – American Outlaws in 2016.

More than just a collaboration, The Highwaymen symbolized creative freedom and the rejection of convention in country music. Despite Jennings’ and Cash’s declining health in the late ’90s, the group’s legacy endured. Nelson and Kristofferson occasionally reunited to perform in tribute to their fallen bandmates before Kristofferson’s death in 2024, keeping the spirit of The Highwaymen alive. The supergroup’s impact on country music is undeniable, leaving behind a lasting influence that continues to inspire generations of artists.

Highwayman (1985)

Released 1985

Highwayman is the debut studio album by country music supergroup The Highwaymen, consisting of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Released in 1985 on Columbia Records, the album was produced by Chips Moman, a figure known for his work with Elvis Presley and numerous country and rock icons. The group came together in Montreux, Switzerland, after performing together for a Christmas special in 1984, where they realized their voices and styles blended perfectly. Recording sessions for Highwayman took place at Moman’s Nashville studio, the Music Mill, capturing a unique sound that brought together their distinct outlaw country styles into a cohesive blend of storytelling and musical mastery. Marty Stuart also contributed, playing guitar and mandolin on the album.

The title track, “Highwayman,” written by Jimmy Webb, became a number one hit on the Billboard Country chart and quickly cemented the group’s success. The album featured other standout tracks like “Desperados Waiting for a Train,” a Guy Clark cover that reached the Top 20, and “Big River,” a reworked version of Cash’s earlier hit, this time with contributions from Jennings. The group’s vocals were evenly shared, with each member taking leads on different tracks, and their camaraderie is palpable throughout the recording. Critically, Highwayman was lauded for its rawness and authenticity, with AllMusic giving it high praise for living up to its leadoff hit. However, some critics noted occasional overproduction with the inclusion of synthesizers. Despite this, Highwayman achieved significant commercial success, topping the US Top Country Albums chart and going Platinum in both the United States and Australia.

CD Track Listings:

“Highwayman” – 3:00
“The Last Cowboy Song” – 3:08
“Jim, I Wore a Tie Today” – 3:20
“Big River” – 2:45
“Committed to Parkview” – 3:18
“Desperados Waiting for a Train” – 4:34
“Deportee (Plane Wreck at Los Gatos)” – 3:45
“Welfare Line” – 2:34
“Against the Wind” – 3:46
“The Twentieth Century Is Almost Over” – 3:33

Highwayman 2 (1990)

Released 1990

Highwayman 2 is the second studio album by The Highwaymen, the legendary country supergroup comprised of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Released in 1990 on Columbia Records, this album marked a notable moment in country music history, with the four country giants reuniting for another round of storytelling and collaboration. This time around, producer Chips Moman, who had worked on the first Highwayman album and had a long history with Nelson, was back behind the board. Recording sessions took place in Nashville, Memphis, and Spicewood, Texas, with additional contributions from a stellar lineup of session musicians. The sound of the album, while rooted in country, carried a slightly more contemporary feel, incorporating elements that some might argue brought a rock edge to the tracks.

The album’s lead single, “Silver Stallion,” reached number 25 on the charts and was accompanied by a memorable music video. While Highwayman 2 didn’t achieve the massive success of its predecessor, it still climbed to number 4 on the country charts and stayed there for 40 weeks. Critical reception was mixed, with some praising the continuation of the supergroup’s chemistry, while others felt the production leaned too heavily on the 1980s studio sound, which hadn’t aged well. Despite these criticisms, the album showcases the unique blend of each member’s distinct voice and musical style, especially on tracks like “Born and Raised in Black and White,” written by Don Cook and John Barlow Jarvis, and “Angels Love Bad Men,” co-written by Jennings.

Musically, Highwayman 2 featured Willie Nelson on guitar, Johnny Cash on vocals, Waylon Jennings on vocals, and Kris Kristofferson on vocals, with support from talented session players like Gene Chrisman on drums, Mike Leech on bass, and Reggie Young on guitar. Mickey Raphael contributed harmonica, and Bobby Emmons and Bobby Wood added layers of keyboards. The resulting sound, though slightly more polished than fans of the outlaw country movement might expect, still carried the weight of four country legends coming together to tell stories of America, its people, and its heartaches.

CD Track Listings:

“Silver Stallion” – 3:12
“Born and Raised in Black and White” – 4:01
“Two Stories Wide” – 2:35
“We’re All in Your Corner” – 3:04
“American Remains” – 4:07
“Anthem ’84” – 2:43
“Angels Love Bad Men” – 3:33
“Songs That Make a Difference” – 2:55
“Living Legend” – 3:59
“Texas” – 2:39

The Road Goes on Forever (1995)

Released 1995

The Road Goes on Forever is the third and final studio album by The Highwaymen, the legendary country supergroup consisting of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Released on April 4, 1995, by Liberty Records, the album followed the success of their previous two releases and showcased the enduring talents of these four iconic artists. Produced by Don Was, the album was recorded at various studios, including Ocean Way Recording in Los Angeles. This time, the group continued to explore the outlaw country genre that had brought them fame, with a combination of original songs and covers, offering a poignant reflection on life, love, and the passing of time.

The Road Goes on Forever includes notable tracks like “The Devil’s Right Hand,” a Steve Earle composition, and the title track, written by Robert Earl Keen. The album’s production is tight and polished, with contributions from a stellar group of musicians such as Kenny Aronoff on drums, Benmont Tench on Hammond organ, and Michael Rhodes on bass. The distinct voices and styles of Cash, Jennings, Nelson, and Kristofferson come together seamlessly, as evidenced on songs like Billy Joe Shaver’s “Live Forever” and Johnny Cash’s co-written track “Death and Hell.” Critically, the album received praise for its mix of reflective and rebellious themes, though commercially it didn’t achieve the same success as the group’s earlier albums, peaking at number 42 on the U.S. Billboard Top Country Albums chart. Nevertheless, The Road Goes on Forever stands as a fitting farewell from one of country music’s most legendary collaborations.

CD Track Listings:

“The Devil’s Right Hand” – 3:14
“Live Forever” – 2:49
“Everyone Gets Crazy” – 2:55
“It Is What It Is” – 3:40
“I Do Believe” – 3:25
“The End of Understanding” – 2:43
“True Love Travels a Gravel Road” – 3:22
“Death and Hell” – 2:51
“Waiting for a Long Time” – 4:20
“Here Comes That Rainbow Again” – 2:50
“The Road Goes on Forever” – 4:42

2005 Reissue Bonus Tracks:

“If He Came Back Again” – 3:34
“Live Forever” – Johnny Cash Acoustic Demo – 2:12
“I Ain’t Song” – Waylon Jennings Acoustic Demo – 1:56
“Pick Up the Tempo” – Willie Nelson Acoustic Demo – 2:18
“Closer to the Bone” – Kris Kristofferson Acoustic Demo – 2:14
“Back in the Saddle Again” – Acoustic Demo – 0:50

The Essential Highwaymen (2010)

Released 2010

The Essential Highwaymen is a two-CD compilation released on October 26, 2010. The collection combines recordings by The Highwaymen with selections from the individual catalogs of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Its 36-track program includes “Highwayman,” “Silver Stallion,” “The Road Goes On Forever,” and a live 1993 Farm Aid performance of “Desperados Waiting for a Train.”

Disc One

“Highwayman”
“Silver Stallion”
“The Greatest Cowboy of Them All”
“Take It to the Limit” (With Waylon Jennings)
“Help Me Make It Through the Night”
“The Taker”
“Just to Satisfy You”
“Moment of Forever”
“Eye of the Storm”
“The Pilgrim: Chapter 33”
“Sunday Mornin’ Comin’ Down”
“Casey’s Last Ride”
“Born and Raised In Black and White”
“Devil’s Right Hand”
“There Ain’t No Good Chain Gang” (feat. Waylon Jennings)
“The Road Goes On Forever”
“I Wish I Was Crazy Again”
“Desperados Waiting for a Train” (Live April 24, 1993; Farm Aid Concert for America, Ames, Iowa)

Disc Two

“Good Hearted Woman”
“A Backstage Pass”
“How Do You Feel About Foolin’ Around”
“Luckenbach, Texas (Back to the Basics of Love)”
“The Night Hank Williams Came to Town”
“If You Don’t Like Hank Williams”
“Are You Sure Hank Done It This Way”
“Big River”
“Deportee (Plane Wreck At Los Gatos)”
“Me and Bobby McGee”
“The Last Cowboy Song”
“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (Remastered for Buddha – October 30, 2000)
“Even Cowgirls Get the Blues”
“Nowhere Road”
“It Is What It Is”
“Living Legend”
“Love Is the Way”
“Live Forever”

The Highwaymen Live – American Outlaws (2016)

Released 2016

The Highwaymen Live – American Outlaws was released on May 20, 2016, by Legacy Recordings. The 46-song, three-disc live collection captures The Highwaymen in concert and brings together group standards with signature songs associated with Cash, Jennings, Nelson, and Kristofferson.