| 1 | ![Let the Rough Side Drag by Jesse Winchester]() | Let the Rough Side Drag | Jesse Winchester | C Major | 8B | 130 |
| 2 | ![Damned If You Do by Jesse Winchester]() | Damned If You Do | Jesse Winchester | C Major | 8B | 103 |
| 3 | ![Step by Step by Jesse Winchester]() | Step by Step | Jesse Winchester | A Minor | 8A | 172 |
| 4 | ![Lay Down Your Burden by Jesse Winchester]() | Lay Down Your Burden | Jesse Winchester | F Major | 7B | 70 |
| 5 | ![Everybody Knows but Me by Jesse Winchester]() | Everybody Knows but Me | Jesse Winchester | D Major | 10B | 128 |
| 6 | ![Blow On, Chilly Wind by Jesse Winchester]() | Blow On, Chilly Wind | Jesse Winchester | E Major | 12B | 119 |
| 7 | ![Working in the Vineyard by Jesse Winchester]() | Working in the Vineyard | Jesse Winchester | D Minor | 7A | 84 |
| 8 | ![How About You by Jesse Winchester]() | How About You | Jesse Winchester | F Major | 7B | 88 |
| 9 | ![It Takes More Than a Hammer and Nails to Make a House a Home by Jesse Winchester]() | It Takes More Than a Hammer and Nails to Make a House a Home | Jesse Winchester | B Minor | 10A | 117 |
| 10 | ![As Soon a I Get on My Feet by Jesse Winchester]() | As Soon a I Get on My Feet | Jesse Winchester | F♯ Major | 2B | 72 |
| 11 | ![The Only Show in Town by Jesse Winchester]() | The Only Show in Town | Jesse Winchester | E♭ Major | 5B | 96 |
| 12 | ![The Brand New Tennessee Waltz - 1976 Version by Jesse Winchester]() | The Brand New Tennessee Waltz - 1976 Version | Jesse Winchester | A Major | 11B | 148 |