| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Lonesome Whistle | Billy Bragg, Joe Henry | 2:53 | |
| She Loves Me | James McMurtry | 3:01 | |
| Silver & Gold / Before I Grow Too Old | Joe Strummer, The Mescaleros | 2:35 | |
| Lead Me On | Joe Henry, Lisa Hannigan | 4:30 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| The Panama Limited | Tom Rush | 8:23 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| Fishin' Blues | Taj Mahal | 3:04 | |
| I'll Trade You Money for Wine | Robbie Fulks | 4:33 | |
| Hobo's Lullaby | Billy Bragg, Joe Henry | 3:57 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| See the Elephant | James McMurtry | 4:25 | |
| Santa Fe | Eilen Jewell | 4:32 | |
| Dangerous Fun | Jesse Winchester | 2:05 | |
| You Must Go | Lilly Hiatt | 5:02 | |
| Studebaker | Warren Zevon | 2:26 | |
| Melinda Down the Line | Ian Fitzgerald | 5:06 | |
| Sweet Tooth | Dave Rawlings Machine | 5:20 | |
| Take it Out Back | Chuck Brodsky | 3:10 | |
| Dear Doctor | Lee Harvey Osmond, Mary Guathier | 3:35 | |
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| Grave Angels | Joe Henry | 5:31 | |
| Thunderbird | John Hiatt | 4:04 | |
| Somewhere in the Middle (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 2:41 | |
| I'm Not Gonna Cry | Loudon Wainwright III | 2:06 | |
| No Later than Soon | Jim Lauderdale | 2:56 | |
| It's All Over Now, Baby Blue | The Seldom Scene | 3:20 | |
| Ghosts of Our Fathers | Otis Gibbs | 3:46 | |
| Wonderful Life | The Felice Brothers | 4:02 | |
| River Floor | Joe Henry | 4:34 | |
| Somebody Else's Troubles | Steve Goodman | 3:43 | |
| This Old Road | Kris Kristofferson | 3:59 | |
| 36 Cents | The Bacon Brothers | 4:24 | |
| You're Dreaming | The Cactus Blossoms | 3:25 | |
| Train to Jackson | Jeffrey Foucault | 4:17 | |
| King Tide and the Sunny Day Flood | Billy Bragg | 2:59 | |
| Wasteland of the Free | Iris DeMent | 5:15 | |
| Just Like That (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:30 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| Ruby and Carlos | James McMurtry | 6:35 | |
| Not Everything That Counts Can Be Counted | Billy Bragg | 4:13 | |
| Keep Your Distance | Buddy & Julie Miller | 3:49 | |
| Long Black Veil - Remastered 2000 | The Band | 3:01 | |
| Charlie James | Peter Case | 3:06 | |
| Don't You Marry | Billy Bragg, Wilco | 3:14 | |
| A Kiss Before I Go | Ryan Adams & The Cardinals | 2:04 | |
| Jacksonville Skyline | Whiskeytown | 3:00 | |
| You Can't Always Get What You Want | Bill Morrissey, Greg Brown | 4:46 | |
