| The Only Living Boy in New York | Simon & Garfunkel | 3:58 | |
| Big Sky Country | Chris Whitley | 4:45 | |
| Gettin' By, High and Strange | Kris Kristofferson | 2:34 | |
| Don’t Lose Your Mind | Lukas Nelson and Promise of the Real | 4:58 | |
| To Love Somebody | Karl Blau | 3:20 | |
| Going To The Country | Bruce Cockburn | 3:16 | |
| Accidentally Like a Martyr | Warren Zevon | 3:06 | |
| After All These Years - 2006 Remaster | T Bone Burnett | 3:12 | |
| Way Out West | Marty Stuart And His Fabulous Superlatives | 5:41 | |
| To Beat the Devil | Kris Kristofferson | 4:41 | |
| Danko/Manuel | Drive-By Truckers | 5:47 | |
| Oh Soul | Mary Gauthier | 5:26 | |
| Day In The Sun | Neal Casal | 5:02 | |
| I Think Its Going to Work Out Fine | Ry Cooder | 4:44 | |
| Me and Bobby McGee | Kris Kristofferson | 4:20 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Grandma's Hands (feat. Mavis Staples) | Willie Nelson, Mavis Staples | 3:10 | |
| No Reason to Quit | Merle Haggard, Willie Nelson | 3:15 | |
| Ballad of Easy Rider | The Byrds | 2:04 | |
| Accidentally Like a Martyr | Warren Zevon | 3:42 | |
| Songbird | Eric Clapton, Willie Nelson | 2:55 | |
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| Standing In My Shoes | Leo Kottke | 3:59 | |
| Southbound Train - Remastered Version | Graham Nash, David Crosby | 3:55 | |
| Purple Heather | Van Morrison | 5:43 | |
| Me and Paul | Willie Nelson | 3:48 | |
| Dusty Old Man | Tift Merritt | 3:47 | |
| History of Lovers | Calexico, Iron & Wine | 3:09 | |
| A World of Hurt | Drive-By Truckers | 4:51 | |
| Take It to the Limit | Waylon Jennings, Willie Nelson | 3:46 | |
| Back In the High Life Again | Warren Zevon | 3:13 | |
| Sandusky | Uncle Tupelo | 3:43 | |
| Carl Perkins' Cadillac | Drive-By Truckers | 5:26 | |
| Farewell Angelina | Tim O'Brien | 4:23 | |
| Long Black Veil - Remastered 2000 | The Band | 3:01 | |
| Lebanon, Tennessee | Ron Sexsmith | 2:57 | |
| My Own Peculiar Way | Willie Nelson | 3:37 | |
| Tell Moses | Colvin & Earle | 3:41 | |
| Stick with Me Baby | Robert Plant, Alison Krauss | 2:49 | |
| Suit Of Lights | Alejandro Escovedo | 4:25 | |
| Love Has Come For You | Steve Martin, Edie Brickell | 3:08 | |
| This Morning I Am Born Again | Slaid Cleaves | 3:56 | |
| Oh, Sister [Feat. Courtney Marie Andrews] | Logan Ledger, Courtney Marie Andrews | 3:40 | |
| Sit & Listen To The Rain | Whiskeytown | 4:05 | |
| Hockey Skates | Kathleen Edwards | 4:28 | |
| We Don't Run | Willie Nelson | 3:01 | |
| Asking For Flowers | Kathleen Edwards | 5:02 | |
| Hallelujah | Willie Nelson | 4:52 | |
| Rings | Leo Kottke | 2:51 | |
| When I Cross Over | Tift Merritt | 6:32 | |
