| 1 | Helpless Crosby, Still, Nash & Young cover
Tour debut
Ryan Adams, Chip Robinson, Kenny Roby, Caitlin Cary | | |
| 2 | Born Yesterday |  |
| 3 | Funny How I'm Losing You |  |
| 4 | To Be The One |  |
| 5 | Hey There, Mrs. Lovely |  |
| 6 | Oh My Sweet Valentine |  |
| 7 | Folklore |  |
| 8 | Theme For A Trucker Tour debut
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| 9 | Nighttime Gals Tour debut
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| 10 | Desperate Ain't Lonely Tour debut
with Caitlin Cary (fiddle; vocals) |  |
| 11 | Crazy Lonesome Tour debut
with Caitlin Cary (fiddle; vocals) |  |
| 12 | My Heart Is Broken with Caitlin Cary (fiddle; vocals) |  |
| 13 | Dancing With The Women At The Bar with Caitlin Cary (fiddle; vocals) |  |
| 14 | The Battle with Caitlin Cary (fiddle; vocals) |  |
| 15 | Burning Bed The Backsliders cover
Live debut
Ryan Adams, Chip Robinson, Kenny Roby, Caitlin Cary | | |
| 16 | Cold Steel Brace 6 String Drag cover
Live debut
Ryan Adams, Chip Robinson, Kenny Roby, Caitlin Cary | | |
| 17 | 16 Days Tour debut
Ryan Adams, Chip Robinson, Kenny Roby, Caitlin Cary |  |