| # | Title | Artist | Rating | Length |
|---|
| 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- recorded in:
- Nashville, Tennessee, United States (on 1984-10-03)
- assistant engineer:
- Ken Criblez and Larry Greenhill
- engineer:
- David Cherry and Chips Moman
- producer:
- Chips Moman
- bass:
- Mike Leech (on 1984-10-03) and Jimmy Tittle (on 1984-10-03)
- drums (drum set):
- Gene Chrisman (on 1984-10-03)
- guitar:
- Paul Davis (on 1984-10-03), Waylon Jennings (on 1984-10-03), Kris Kristofferson (on 1984-10-03), Chips Moman (on 1984-10-03), Willie Nelson (on 1984-10-03) and Johnny Rodriguez (on 1984-10-03)
- harmonica:
- Mickey Raphael (on 1984-10-03)
- keyboard:
- Paul Davis (on 1984-10-03), Bobby Emmons (on 1984-10-03) and Bobby Wood (on 1984-10-03)
- mandolin:
- Marty Stuart (on 1984-10-03)
- background vocals:
- Johnny Cash (on 1984-10-03), Paul Davis (on 1984-10-03), Waylon Jennings (on 1984-10-03), Kris Kristofferson (on 1984-10-03), Chips Moman (on 1984-10-03), Willie Nelson (on 1984-10-03) and Johnny Rodriguez (on 1984-10-03)
- vocals:
- Johnny Cash (on 1984-10-03), Waylon Jennings (on 1984-10-03), Kris Kristofferson (on 1984-10-03) and Willie Nelson (on 1984-10-03)
- performer:
- Johnny Cash , Waylon Jennings , Kris Kristofferson and Willie Nelson
- phonographic copyright (℗) by:
- CBS Records Inc. (in 1985), CBS, Inc. (in 1985), Sony BMG Music Entertainment (in 1985), Sony Music Entertainment (in 1985) and Sony Music Entertainment Inc. (in 1985, in 2003)
- recorded at:
- Moman's Recording Studio in Nashville, Tennessee, United States (on 1984-10-03) and Woodland Sound Studios in Nashville, Tennessee, United States (on 1984-10-03)
- part of:
- Grammy Award: Best Country Performance by a Duo or Group nominees (number: 1986)
- cover recording of:
- The Highwayman (on 1984-10-03)
- lyricist and composer:
- Jimmy Webb
- publisher:
- White Oak Songs
- recording of:
- The Highwayman
- lyricist and composer:
- Jimmy Webb
- publisher:
- White Oak Songs
| The Highwaymen | 4.45 | 3:03 |