| May We Love | Grayson Capps | 5:03 | |
| South Wind of Summer | The Flatlanders | 4:46 | |
| Harmony Two (feat. Shannon McNally) | Terry Allen, The Panhandle Mystery Band, Shannon McNally | 5:45 | |
| The Thirty-third of August | Mickey Newbury | 5:42 | |
| 'Til I Get It Right | John Doe, The Sadies | 3:19 | |
| Sundown Blues | Tony Joe White | 4:47 | |
| Bird On the Wire | Tim Hardin | 5:27 | |
| Hillbilly Blue (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:11 | |
| Sabine River | Ray Bonneville | 4:46 | |
| I'll Let You Pick a Window | Barna Howard | 3:34 | |
| The Beast in Me | Nick Lowe | 2:28 | |
| Don't Skip Out on Me | Richmond Fontaine | 4:07 | |
| Story of You | The Flatlanders | 2:00 | |
| Going Going Gone | Emma Swift | 3:30 | |
| Sleeping Woman | Delaney Davidson | 3:46 | |
| Bakersfield | Vic Chesnutt | 2:26 | |
| Makes Me Wonder If I Ever Said Goodbye | Mickey Newbury | 2:48 | |
| In My Hour of Darkness - 2002 Remaster | Gram Parsons | 3:49 | |
| Hasten Down the Wind | Warren Zevon | 2:32 | |
| River Song | Tom Rush | 3:33 | |
| A Whiter Shade of Pale | Dan Reeder | 3:36 | |
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| The Bottom of the World | Bottom of the World | 4:30 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| Unforgiven | Tim Hardin | 3:22 | |
| Almost Persuaded ft. John Paul White | Lera Lynn, John Paul White | 3:11 | |
| Stars | Fred Eaglesmith | 3:16 | |
| Mandolin Wind | Amy Helm | 5:52 | |
| Sunshine, Pt. 1 | Mickey Newbury | 4:26 | |
| I Should Have Said | Bap Kennedy | 3:17 | |
| Like A Songbird That Has Fallen | Luther Dickinson, Amy Helm | 2:54 | |
| Conjure Child | Tony Joe White | 5:32 | |
| Kansas | Fred Eaglesmith | 3:44 | |
| Bodysnatchers | Dave Rawlings Machine | 5:56 | |
| If I Cant Win | The Cactus Blossoms | 3:17 | |
| Write a Song a Song / Angeline | Mickey Newbury | 7:12 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| Ditch | Sam Baker | 1:56 | |
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | |
| You're Dreaming | The Cactus Blossoms | 3:25 | |
| Till I'm Too Old to Die Young (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:29 | |
| Memphis Rain | Aaron Lee Tasjan | 3:38 | |
| All The Money I Had Is Gone | The Deep Dark Woods | 4:08 | |
| Chasin' Wild Horses | Bruce Springsteen | 5:03 | |
| Method Acting / Cortez The Killer | Dave Rawlings Machine | 10:20 | |
| I Think I'll Take To Whiskey | Jesse Colin Young | 2:50 | |
| Go, Leave | Allison Moorer | 3:40 | |
| Close The Door Lightly | Eric Andersen | 3:50 | |
| Emotionally Yours | Bettye LaVette | 5:24 | |
| Rye Whiskey | Jesse Colin Young | 4:54 | |
