The Highwaymen Vinyl Records Lps For Sale
Check out these new and used The Highwaymen vinyl records LPs for sale. We recommend starting your The Highwaymen vinyl collection with the essential albums The Last Cowboy Song, Jim, I Wore A Tie Today and Big River. Our inventory is always changing, so check back often, or browse our list of vinyl records for sale from country musicians.
Live At Nassau Coliseum
The Highwaymen Aberdeen FM 1992 Records & LPs
42% Off
Highwayman
14% Off
The Highwaymen Vinyl Collection: Highwayman / Highwayman 2 / + Including Bonus Art Card
$89.36 (as of July 29, 2025 00:14 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Highwaymen Artists: An Untold Truth
The Highwaymen
$4.83 (as of July 29, 2025 00:17 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
The Highwaymen (Music From the Film)
$45.51 (as of July 29, 2025 00:17 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
![Frankie & Johnny [Vinyl LP] #1](https://m.media-amazon.com/images/I/51k9sfWcb-L._SL100_.jpg)
Frankie & Johnny [Vinyl LP]
68% Off
HIGHWAYMEN - Hioghwayman 2 1990 import LP
$99.90 (as of July 29, 2025 18:18 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Live Highwaymen [VINYL]
$40.67 (as of July 29, 2025 18:19 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
The Highwaymen: Country’s Greatest Supergroup
A Country Music Dream Team
The Highwaymen were more than a band—they were a living, breathing embodiment of outlaw country music. Comprised of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson, The Highwaymen brought together four of the most legendary voices in country music history. Each artist had already built a towering solo career, but together they formed a supergroup that carried the rebellious spirit of outlaw country into a new era. Their collaboration wasn’t just a marketing gimmick; it was a powerful statement of unity, freedom, and authenticity.
Formation and Chemistry
The Highwaymen officially came together in the mid-1980s, though their friendships and collaborations stretched back decades. All four members had shared stages, studios, and stories long before the idea of a group was formalized. They were united by a mutual respect and a common philosophy: break the rules when necessary, sing from the heart, and never let the Nashville machine dictate your sound.
The name “Highwaymen” was inspired by the Jimmy Webb song “Highwayman,” which they recorded as the title track for their first album. The song, with its narrative about reincarnation and timeless spirit, perfectly captured their larger-than-life personas. Each member took a verse, telling the story of a soul that lives on through different lives—a fitting metaphor for their enduring legacies.
Notable Albums and Songs
- Highwayman (1985)
This debut album set the tone for everything that followed. The title track, “Highwayman,” became a number one country hit and remains one of the most iconic songs in the genre. The album also featured “Desperados Waiting for a Train,” a Guy Clark cover that highlighted the group’s love for strong storytelling. Highwayman was a mix of old-soul country ballads and rebellious anthems, drawing on each member’s unique strengths. The chemistry between the four legends was immediate and electric. - Highwayman 2 (1990)
Their sophomore effort was more polished but still retained the spirit of their debut. Songs like “Silver Stallion” and “Born and Raised in Black and White” dealt with themes of brotherhood, identity, and freedom. “Silver Stallion” in particular became a fan favorite, with its haunting imagery and harmonies. While not as commercially successful as their first album, Highwayman 2 deepened the group’s legacy and showcased their evolving dynamic. - The Road Goes on Forever (1995)
This final studio album brought the group back for one last ride. Produced by Don Was, it had a slightly modern edge but stayed true to their outlaw roots. The title track, written by Robert Earl Keen, told a vivid tale of lovers on the run, delivered with grit and soul. “It Is What It Is” and “If He Came Back Again” are other standout tracks, blending introspection with the swagger you’d expect from country music’s most legendary rebels. Though this album didn’t top the charts, it solidified The Highwaymen as more than a nostalgic act—they were still making meaningful music right up to the end.
Outlaw Country and The Highwaymen’s Mission
Each member of The Highwaymen had already rejected the slick, formulaic style of 1970s Nashville country music before the group even formed. Waylon Jennings and Willie Nelson led the charge of the outlaw country movement, demanding artistic freedom and creating albums on their own terms. Johnny Cash had always been a maverick, with songs that challenged authority and embraced the outsider. Kris Kristofferson brought poetic songwriting and a cinematic touch to country music, reshaping what a country lyric could be.
Together, The Highwaymen stood for everything that movement represented. They wore their independence like a badge of honor. The music wasn’t about fitting in—it was about standing tall, telling honest stories, and creating songs that mattered.
Stage Presence and Brotherhood
One of the most compelling aspects of The Highwaymen was their live performances. Whether they were trading verses on stage or stepping aside to let each other shine, the camaraderie between them was undeniable. They weren’t just sharing the spotlight—they were amplifying each other’s greatness.
They often introduced each other with warmth and humor, showing genuine affection that resonated with audiences. The concerts were as much about personality as they were about music. Fans came to see the legends, but they left feeling like they’d witnessed something deeper: a rare kind of brotherhood formed through decades of shared roads, fights, victories, and late-night studio sessions.
The Highwaymen - Live At Nassau Coliseum NEW Vinyl
 | $23.99 Buy It on eBay for only: $23.99 Buy It Now on eBay |
The Highwaymen – Live At Nassau Coliseum AMAZON VERSION Clear Vinyl 2016 RARE
 | $249.00 Buy It on eBay for only: $249.00 Buy It Now on eBay |
The Highwaymen - Live At Nassau Coliseum [Used Very Good Vinyl LP]
 | $23.23 Buy It on eBay for only: $23.23 Buy It Now on eBay |
The Highwaymen, Vinyl Records LP
 | $4.79 Buy It on eBay for only: $4.79 Buy It Now on eBay |
The Highwaymen S/T Self Titled Vinyl LP NM/ A 1960 1st U.S. Pressing Michael
 | $11.95 Buy It on eBay for only: $11.95 Buy It Now on eBay |
45 RECORD - THE HIGHWAYMEN - MICHAEL
 | $1.10 Buy It on eBay for only: $1.10 Buy It Now on eBay |
Picture Sleeve 45 Highwaymen - Highwayman / Human Condition (Cash Willie Waylon)
 | $19.99 Buy It on eBay for only: $19.99 Buy It Now on eBay |
THE HIGHWAYMEN LP 12" VINYL RECORD MONO (UAL 3125) *QUICK SHIP*
 | $5.00 Buy It on eBay for only: $5.00 Buy It Now on eBay |
The Highwaymen: Stop! Look! & Listen! Lp
 | $6.99 Buy It on eBay for only: $6.99 Buy It Now on eBay |
The Highwaymen – Standing Room Only! - LP 1961 United - Folk
 | $3.25 Buy It on eBay for only: $3.25 Buy It Now on eBay |
Influence on Future Artists
The Highwaymen influenced not just individual musicians, but the entire culture of country music. They proved that older artists could remain vital and relevant when they stayed true to themselves. They also set a template for future supergroups and collaborations—showing that combining star power could result in real artistry, not just spectacle.
Modern country and Americana artists like Sturgill Simpson, Jason Isbell, Chris Stapleton, and Brandi Carlile have drawn inspiration from the outlaw tradition The Highwaymen helped popularize. These younger musicians value the same things—honest lyrics, emotional depth, and creative freedom.
Even outside country, artists like Bruce Springsteen, Johnny Depp, and Eddie Vedder have expressed admiration for The Highwaymen’s ethos and storytelling power. Their reach went far beyond honky-tonks and Nashville studios—they became cultural icons of resistance, independence, and authenticity.
Legacy and Lasting Impact
Though all four members continued with solo careers after their final album, The Highwaymen remained a defining chapter in each of their stories. When Johnny Cash passed away in 2003, followed by Waylon Jennings in 2002, fans mourned not just the loss of individuals, but the end of a mythic era.
Their legacy lives on through their recordings, live footage, and the influence they’ve had on generations of musicians. The Highwayman song itself has become a symbol of immortality in music, reflecting the way these men passed through time, each in their own way, but always leaving something meaningful behind.
In a world where the music industry often feels manufactured and profit-driven, The Highwaymen remind us what happens when artists take control of their art. They weren’t built by label executives or marketing departments—they were forged in smoke-filled clubs, tour buses, jailhouses, and the open road.
Conclusion: More Than Music
The Highwaymen were more than the sum of their parts. They were a celebration of friendship, freedom, and real country music. Their songs carried weight, their presence carried history, and their bond carried through every performance. In a genre built on storytelling, few stories are more compelling than that of The Highwaymen—four rebels, riding together, leaving behind a legacy that still echoes on dusty roads and endless highways.
Minecraft - Volume Alpha
16% Off
Hybrid Theory
16% Off
AM
13% Off
Ctrl
22% Off
Greatest Hits
10% Off
Abbey Road (Anniversary Edition)[LP]
23% Off
![hickey [Platinum LP] [Alt Cover] [Amazon Exclusive] #1](https://m.media-amazon.com/images/I/51RICroSGhL._SL100_.jpg)
hickey [Platinum LP] [Alt Cover] [Amazon Exclusive]
$32.99 (as of July 29, 2025 13:55 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
![Legend [Vinyl] #1](https://m.media-amazon.com/images/I/611La+6Hi9L._SL100_.jpg)
![Legend [Vinyl] #2](https://m.media-amazon.com/images/I/31nfAYBov8L._SL100_.jpg)
![Legend [Vinyl] #3](https://m.media-amazon.com/images/I/21h7ykrSuuL._SL100_.jpg)
![Legend [Vinyl] #4](https://m.media-amazon.com/images/I/318kzRTVolL._SL100_.jpg)
![Legend [Vinyl] #5](https://m.media-amazon.com/images/I/31vjgY6+u5L._SL100_.jpg)
Legend [Vinyl]
7% Off
Parachutes
$24.98 (as of July 29, 2025 16:12 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
![HIT ME HARD AND SOFT[Recycled Black LP] #1](https://m.media-amazon.com/images/I/3189N1z40uL._SL100_.jpg)
HIT ME HARD AND SOFT[Recycled Black LP]
![[Exquisite Appearance] Built from wood and metal materials with a unique sense of layering; The streamlined corner design is truly atmospheric and stylish(Note: long hold the start button to turn the power on, and press again to start) [All in 1] Thi...](https://m.media-amazon.com/images/I/41vovGjFkeL._SL160_.jpg)
1 by ONE High Fidelity Belt Drive Turntable with Built-in Speakers, Vinyl Record Player with Magnetic Cartridge, Bluetooth Playback and Aux-in Functionality, Auto Off
$219.99 (as of July 29, 2025 16:06 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Audio-Technica AT-LP60X-BK Fully Automatic Belt-Drive Stereo Turntable, Black, Hi-Fidelity, Plays 33 -1/3 and 45 RPM Vinyl Records, Dust Cover, Anti-Resonance, Die-Cast Aluminum Platter
$199.00 (as of July 29, 2025 16:12 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Bluetooth Vinyl Record Player,3-Speed Turntable with Stereo Speakers Vintage Phonograph Record Player, with RCA Line Out AUX in Headphone Jack (Brown)
$39.99 (as of July 29, 2025 16:06 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Audio-Technica AT-LP60XBT-BK Fully Automatic Wireless Belt-Drive Turntable (Black) (ATLP60XBTBK)
$299.00 (as of July 29, 2025 16:12 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Sony PS-LX310BT Belt Drive Turntable: Fully Automatic Wireless Vinyl Record Player with Bluetooth and USB Output Black
$448.00 (as of July 29, 2025 13:55 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)
Vinyl Record Player 3-Speed Bluetooth Suitcase Portable Belt-Driven Record Player with Built-in Speakers RCA Line Out AUX in Headphone Jack Vintage Turntable
38% Off
Crosley Miles Vinyl Record Player with Speakers - 3-speed Bluetooth turntable, built-in stereo speakers, aux output - Elegant wood and gold design - Play 33/45/78 RPM or stream music
$207.81 (as of July 29, 2025 16:12 GMT +00:00 - More infoProduct prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on [relevant Amazon Site(s), as applicable] at the time of purchase will apply to the purchase of this product.)![[Moving Magnet Cartridge] The included high-quality AT Moving Magnet-type cartridge and stylus produces rich, warm audio and outstanding sound clarity. While an universal headshell allows users to change cartridges with ease [Bluetooth Connectivity] ...](https://m.media-amazon.com/images/I/317hRd0b1EL._SL160_.jpg)
