| # | Title | Artist | Rating | Length |
|---|
| 1 | Ruby. Don’t Take Your Love to Town | Kenny Rogers | 3.65 | 2:58 |
| 2 | It’s Five O’Clock Somewhere | Alan Jackson & Jimmy Buffett | 4 | 3:50 |
| 3 | He Stopped Loving Her Today | George Jones | 5 | 3:17 |
| 4 | I Recall a Gypsy Woman | Don Williams | 3 | 3:24 |
| 5 | She Used to Love Me a Lot | David Allan Coe | 4 | 3:04 |
| 6 | Don’t It Make My Brown Eyes Blue | Crystal Gayle | 4.4 | 2:32 |
| 7 | Blanket on the Ground | Billie Jo Spears | | 3:31 |
| 8 | Coal Miner’s Daughter | Loretta Lynn | 4 | 3:00 |
| 9 | Angel of the Morning | Juice Newton | 4.35 | 4:10 |
| 10 | Passionate Kisses | Mary Chapin Carpenter | 4 | 3:22 |
| 11 | 500 Miles Away From Home | Bobby Bare | 3.5 | 2:43 |
| 12 | Song of the South | Alabama | 3.85 | 3:11 |
| 13 | Are You Sure Hank Done It This Way | Waylon Jennings | | 2:55 |
| 14 | Leader of the Band | Dan Fogelberg | 2 | 4:17 |
| 15 | I Think I’ll Just Stay Here and Drink | Merle Haggard | | 3:39 |
| 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 |
| 17 | Walk a Mile in My Shoes | Joe South | | 4:07 |
| 18 | The Night They Drove Old Dixie Down | The Band | 4.4 | 3:31 |
| 19 | It’s Hard to Be Humble (live) | Mac Davis | | 4:21 |
| 20 | Convoy | C.W. McCall | 5 | 3:50 |