| # | Title | Artist | Length |
|---|
| 1 | Fireside Chat, Part 1 | Franklin D. Roosevelt | 0:45 |
| 2 | Breadline Blues 1932 | Bernard Smith | 1:35 |
| 3 | Moneyland | The Del McCoury Band | 3:56 |
| 4 | Farmer's Blues | Marty Stuart & Merle Haggard | 3:21 |
| 5 | What Happened? | Merle Haggard | 3:44 |
| 6 | Medley: I Wonder How the Old Folks Are at Home/I'd Rather Live by the Side of the Road | Mac Wiseman | 3:07 |
| 7 | When I'm 64 | The Del McCoury Band | 2:35 |
| 8 | 40 Acres and a Fool | The Del McCoury Band | 4:05 |
| 9 | A Train Not Running | Chris Knight | 3:55 |
| 10 | You'll Never Leave Harlan Alive | Patty Loveless | 6:07 |
| 11 | Mama's Hungry Eyes | Emmylou Harris with Rodney Crowell | 3:39 |
| 12 | Carry Me Across the Mountain | Dan Tyminski | 2:34 |
| 13 | If We Make It Through December | Merle Haggard | 2:43 |
| 14 | The Way It Is | Bruce Hornsby & the Fairfield Four | 5:23 |
| 15 | Breadline Blues 2008 | Del McCoury, Mac Wiseman, Tim O’Brien, Gillian Welch & David Rawlings | 3:08 |
| 16 | Fireside Chat, Part 2 | Franklin D. Roosevelt | 5:12 |
