| The Thirty-third of August | Mickey Newbury | 5:42 | |
| Hello Cruel World | Gretchen Peters | 4:24 | |
| Where I'm From | Shelby Lynne | 3:50 | |
| Saving the Good Stuff for You | Richard Thompson | 3:54 | |
| Nothing Good Can Come from This | Amy Speace | 3:11 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| True Love Travels on a Gravel Road | Nick Lowe | 3:36 | |
| Shiver Me Timbers | Tom Waits | 4:26 | |
| Me and Bobby McGee | Gordon Lightfoot | 3:46 | |
| I Saw A Stranger With Your Hair | John Gorka | 4:03 | |
| Oh Marianne | Peter Wolf | 4:19 | |
| Wildfire | Watchhouse | 5:29 | |
| Fool Who Knows | Little Village | 3:45 | |
| The Water is Wide | John Gorka | 4:28 | |
| Unequal Love | Crosby, Stills & Nash | 4:46 | |
| Leave The Light On | Chris Smither | 3:47 | |
| Hope I Don't Fall in Love with You | Tom Waits | 5:01 | |
| Homeward Bound | Simon & Garfunkel | 2:29 | |
| Where Has My Easy Gone | Ray Bonneville | 3:47 | |
| The Things That We Are Made Of | Mary Chapin Carpenter | 5:30 | |
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| I Ain't Got No Home | Bruce Springsteen | 3:40 | |
| Sandusky | Uncle Tupelo | 3:43 | |
| Hell Bent of a Heartache | Guy Clark | 3:34 | |
| When the Nights Are Cold | Joe Ely | 2:53 | |
| 2 Dollar Shoes | Rosie Thomas | 3:10 | |
| Who Holds Your Hand | Patty Larkin | 3:07 | |
| If We Don't (with Alison Krauss) - from the Dumplin' Original Motion Picture Soundtrack | Dolly Parton, Rhonda Vincent, Alison Krauss | 2:28 | |
| Private Thoughts | Chip Taylor, Carrie Rodriguez | 4:01 | |
| Old Soldier | David Crosby | 4:58 | |
| Slowpoke | Crosby, Stills, Nash & Young | 4:31 | |
| Forever Young - From NBC's Parenthood | Rhiannon Giddens, Iron & Wine | 4:21 | |
| Morning Is My Destination | Tift Merritt | 3:17 | |
| Baby, Now That I've Found You | Alison Krauss | 3:48 | |
| City Girls | J.J. Cale | 2:49 | |
| I Shall Be Released - Remastered 2000 | The Band | 3:12 | |
| Graduation Day | Chris Isaak | 3:10 | |
| Rich Woman | Robert Plant, Alison Krauss | 4:03 | |
| Tonight Will Be Fine | Teddy Thompson | 3:36 | |
| Far Away Eyes - Remastered | The Rolling Stones | 4:23 | |
| Congratulations | Traveling Wilburys | 3:29 | |
| Waiting For The Sun | The Jayhawks | 4:20 | |
| Oh, Atlanta | Alison Krauss | 4:43 | |
| I'm Still Loving You | Blackie & The Rodeo Kings | 4:27 | |
| Gone Gone Gone (Done Moved On) | Robert Plant, Alison Krauss | 3:32 | |
| I'd Run Away | The Jayhawks | 3:33 | |
| Make The World Go Away | Jamey Johnson, Alison Krauss | 3:03 | |
| Holding Up the Sky | Buddy & Julie Miller | 3:09 | |
| Waiting On A Friend - Remastered 2009 | The Rolling Stones | 4:34 | |