The Highwaymen
| Company type | Supergroup |
|---|---|
| Industry | Music |
| Founded | 1985 |
| Founder | Johnny Cash, Waylon Jennings, Willie Nelson, Kris Kristofferson |
| Defunct | 1995 (active period) |
Area served | United States |
Key people | Johnny Cash, Waylon Jennings, Willie Nelson, Kris Kristofferson |
| Products | Studio albums, singles, music videos |
The Highwaymen represented a prominent American country music supergroup composed of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Their active period spanned from 1985 through 1995, during which they produced three studio albums under major labels: two released via Columbia Records and one through Liberty Records. Among their Columbia releases, three singles charted successfully, highlighted by the chart-topping 1985 single "Highwayman."
On the Highwayman album, Johnny Rodriguez provided Spanish-language vocals for the track "Deportee." Additionally, all four members appeared together in the 1986 motion picture Stagecoach.
In 1990, the original ensemble known as the folk group from the 1950s and ’60s initiated legal action concerning the use of the name inspired by a song from Jimmy Webb. This dispute was resolved when a nonexclusive license was granted to the supergroup, after which both bands performed jointly at a Hollywood concert that same year.
Highwayman
The group’s inception in 1985 saw their first two albums released without an official band name, instead credited as "Nelson, Jennings, Cash, Kristofferson." Their debut record, Highwayman, produced by Chips Moman, included the #1 country single "Highwayman" as well as a Top 20 rendition of Guy Clark’s "Desperados Waiting for a Train."
Highwayman 2
Reuniting in 1990, they issued Highwayman 2, which peaked at #4 on the country albums chart. The lead track, "Silver Stallion", originally by Lee Clayton, reached the Top 40. Once again produced by Moman, this album garnered a Grammy nomination for Best Country Vocal Collaboration and featured six songs penned or co-written by members of the group.
The Road Goes on Forever
Their final studio effort before Jennings’s passing in 2002 was the 1995 album The Road Goes on Forever, produced by Don Was and named after a Robert Earl Keen cover. It contained the single "It Is What It Is." A tenth-anniversary edition was released in 2005, including bonus material and, in select editions, a DVD containing the "It Is What It Is" music video along with the documentary Live Forever – In the Studio with the Highwaymen.
Final years: Breakup, aftermath, and occasional partial reunions
Touring continued into the late 1990s until health issues affecting Jennings and Cash curtailed full-scale tours. Each member returned focus to their solo endeavors; Jennings briefly participated in another country supergroup called Old Dogs before his death in 2002, followed by Cash’s passing in 2003.
Following these losses, Nelson and Kristofferson occasionally collaborated but did not perform under The Highwaymen name. For instance, in November 2003, they joined George Jones to perform Cash’s "Big River" during a Grand Ole Opry tribute concert held at Nashville’s Ryman Auditorium.
Looking back in 2010, Kristofferson remarked, "Those tours and records were an incredible period... I shared the stage with all my idols. These were men whose ashtrays I once cleaned. It amazes me that I wasn’t more amazed."
In 2012, Kristofferson teamed with Jamey Johnson and Snoop Dogg to feature alongside Nelson on the track "Roll Me Up and Smoke Me When I Die."
In 2016, Nelson and Kristofferson issued a virtual collaboration of “One Too Many Mornings,” incorporating archived vocal recordings of Cash and Jennings from the 1980s. This track was included as a bonus on “Live: American Outlaws,” a live album recorded at Nassau Coliseum in 1990.
Kristofferson passed away on September 28, 2024, leaving Nelson as the sole surviving member of The Highwaymen.
Studio albums
| Album Title | Album Information | Highest Chart Rankings | Certifications (sales milestones) | |||||
|---|---|---|---|---|---|---|---|---|
| US Country | US | AUS | CAN Country | DEN | NOR | |||
| Highwayman |
|
1 | 92 | 23 | — | — | — |
|
| Highwayman 2 |
|
4 | 79 | 9 | — | — | — |
|
| The Road Goes On Forever |
|
42 | — | 46 | 10 | 8 | 11 | |
| "—" indicates albums that did not enter the charts | ||||||||
Compilation albums
| Compilation Title | Album Information | Highest Chart Positions | Sales Figures | |
|---|---|---|---|---|
| US Country | AUS | |||
| The Highwaymen Ride Again (Import Only – Greece & Netherlands) |
|
— | — | |
| Highwayman Super Hits |
|
— | — | |
| Country Legends |
|
— | — | |
| The Essential Highwaymen |
|
— | — | |
| Live: American Outlaws |
|
16 | 89 |
|
| The Very Best of the Highwaymen |
|
22 | — |
|
| "—" indicates releases that did not chart | ||||
Singles
| Year of Release | Single Title | Highest Chart Rankings | Associated Album | |||
|---|---|---|---|---|---|---|
| US Country | AUS | CAN Country | CAN AC | |||
| 1985 | "Highwayman" | 1 | 98 | 1 | 19 | Highwayman |
| "Desperados Waiting for a Train" | 15 | — | 20 | — | ||
| 1990 | "Silver Stallion" | 25 | 123 | 21 | — | Highwayman 2 |
| "Born and Raised in Black and White" | —A | — | — | — | ||
| "American Remains" | — | — | — | — | ||
| 1995 | "It Is What It Is" | — | — | — | — | The Road Goes on Forever |
| 2005 | "If He Came Back Again" | "—" | "—" | "—" | "—" | The Road Goes on Forever (re-release) |
Notes:
- A The track "Born and Raised in Black and White" did not appear on Hot Country Songs but reached number one on Hot Country Radio Breakouts.
Music videos
| Year | Title | Director |
|---|---|---|
| 1985 | "Highwayman" | Peter Israelson |
| 1990 | "Silver Stallion" | Jon Small |
| 1995 | "It Is What It Is" | Lowe/Don Was |
| 2016 | "Good Hearted Woman" | Jon Small |
Video albums
| Year | Title | Description | Certification |
|---|---|---|---|
| 1991 | Highwaymen Live! | recorded live in 1990 at the Nassau Coliseum |
|
| 1993 | On the Road Again | captured during a 1992 performance in Aberdeen, Scotland | |
| 2016 | The Highwaymen Live at The Nassau Coliseum | a comprehensive re-edited version of Highwaymen Live!, recorded in 1990 at the Nassau Coliseum |
|