| # | Titolo | Artista | Valutazione | Durata |
|---|
| 1 | Me and Bobby McGee | Kris Kristofferson | 5 | 4:21 |
| 2 | Jody and the Kid | Kris Kristofferson | 4 | 3:07 |
| 3 | Sunday Mornin’ Comin’ Down | Kris Kristofferson | 3.5 | 4:32 |
| 4 | From the Bottle to the Bottom | Kris Kristofferson | 4 | 2:59 |
| 5 | Once More with Feeling | Kris Kristofferson | | 2:51 |
| 6 | For the Good Times | Kris Kristofferson | 4 | 3:25 |
| 7 | The Taker | Kris Kristofferson | 4 | 3:16 |
| 8 | Help Me Make It Through the Night | Kris Kristofferson | 4.5 | 2:23 |
| 9 | Come Sundown | Kris Kristofferson | | 2:38 |
| 10 | The Pilgrim – Chapter 33 | Kris Kristofferson | 3.5 | 3:11 |
| 11 | Loving Her Was Easier (Than Anything I’ll Ever Do Again) | Kris Kristofferson | 4.5 | 3:48 |
| 12 | I’d Rather Be Sorry | Kris Kristofferson feat. Rita Coolidge | 3.5 | 3:12 |
| 13 | Nobody Wins | Kris Kristofferson | 5 | 3:09 |
| 14 | Stranger | Kris Kristofferson | | 3:10 |
| 15 | Why Me | Kris Kristofferson | 4 | 3:29 |
| 16 | Highwayman- registrata a:
- Nashville, Tennessee, Stati Uniti (il 1984-10-03)
- assistente tecnico:
- Ken Criblez e Larry Greenhill
- tecnico:
- David Cherry e Chips Moman
- produttore:
- Chips Moman
- armonica (a bocca) :
- Mickey Raphael (il 1984-10-03)
- basso :
- Mike Leech (il 1984-10-03) e Jimmy Tittle (il 1984-10-03)
- batteria :
- Gene Chrisman (il 1984-10-03)
- chitarra :
- Paul Davis (il 1984-10-03), Waylon Jennings (il 1984-10-03), Kris Kristofferson (il 1984-10-03), Chips Moman (il 1984-10-03), Willie Nelson (il 1984-10-03) e Johnny Rodriguez (il 1984-10-03)
- mandolino :
- Marty Stuart (il 1984-10-03)
- tastiera :
- Paul Davis (il 1984-10-03), Bobby Emmons (il 1984-10-03) e Bobby Wood (il 1984-10-03)
- voce:
- Johnny Cash (il 1984-10-03), Waylon Jennings (il 1984-10-03), Kris Kristofferson (il 1984-10-03) e Willie Nelson (il 1984-10-03)
- voce di accompagnamento:
- Johnny Cash (il 1984-10-03), Paul Davis (il 1984-10-03), Waylon Jennings (il 1984-10-03), Kris Kristofferson (il 1984-10-03), Chips Moman (il 1984-10-03), Willie Nelson (il 1984-10-03) e Johnny Rodriguez (il 1984-10-03)
- esecutore:
- Johnny Cash , Waylon Jennings , Kris Kristofferson e Willie Nelson
- diritti fonografici (℗) detenuti da:
- CBS Records Inc. (nel 1985), CBS, Inc. (nel 1985), Sony BMG Music Entertainment (nel 1985), Sony Music Entertainment (nel 1985) e Sony Music Entertainment Inc. (nel 1985, nel 2003)
- registrata presso:
- Moman's Recording Studio in Nashville, Tennessee, Stati Uniti (il 1984-10-03) e Woodland Sound Studios in Nashville, Tennessee, Stati Uniti (il 1984-10-03)
- parte di:
- Grammy Award: Best Country Performance by a Duo or Group nominees (numero: 1986)
- registrazione cover di:
- The Highwayman (il 1984-10-03)
- paroliere e compositore:
- Jimmy Webb
- editore:
- White Oak Songs
- registrazione di:
- The Highwayman
- paroliere e compositore:
- Jimmy Webb
- editore:
- White Oak Songs
| The Highwaymen | 4.45 | 3:03 |