| Good Guys and Bad Guys | Camper Van Beethoven | 3:56 | |
| Creosote | Son Volt | 4:12 | |
| Wanderin' | Justin Townes Earle | 2:38 | |
| Crazy Man | Freakwater | 2:39 | |
| Sun Comes Up, It's Tuesday Morning | Cowboy Junkies | 3:56 | |
| Rain Roll In | Eilen Jewell | 2:47 | |
| Skyway - 2008 Remaster | The Replacements | 2:06 | |
| Arms Like Boulders | The War On Drugs | 5:20 | |
| Hold On, Hold On | Neko Case | 2:46 | |
| Every Night Is Friday Night (Without You) | Old 97's | 2:45 | |
| Our Song | Joe Henry | 6:19 | |
| My Home Is The Sea | Bonnie Prince Billy, Matt Sweeney | 5:49 | |
| Unwed Fathers (feat. Liz Isenberg) | Deer Tick, Liz Isenberg | 3:39 | |
| All Men Are Liars | Nick Lowe | 3:22 | |
| Willie Mays Is Up at Bat | Chuck Prophet | 4:58 | |
| Ashamed | Deer Tick | 2:13 | |
| Forget the Flowers - 2017 Remaster | Wilco | 2:45 | |
| Still Feeling Blue - 2002 Remaster | Gram Parsons | 2:43 | |
| First Night | The Hold Steady | 4:54 | |
| New England | Jonathan Richman & The Modern Lovers | 2:23 | |
| Sweet Louise | Pete Molinari | 4:04 | |
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| Look the Other Way | Justin Townes Earle | 2:29 | |
| Love the Way You Walk Away | Blitzen Trapper | 3:40 | |
| I Burn Today | Frank Black | 4:05 | |
| Lost Coastlines | Okkervil River | 5:31 | |
| Draft Daughter's Blues aka Ootischenia | The Be Good Tanyas | 3:21 | |
| Back into Your World | Son Volt | 3:45 | |
| Movin' On | Justin Townes Earle | 4:41 | |
| O! Grace | Magnolia Electric Co., Jason Molina | 3:27 | |
| $87 and a guilty Conscience That Gets Worse the Longer I Go | Richmond Fontaine | 3:34 | |
| Mohammed's Radio | Warren Zevon | 3:43 | |
| Won't Be Home | Old 97's | 4:48 | |
| To Call My Own | Golden Smog | 3:31 | |
| If Only You Were Lonely - Twin Tone Single Version | The Replacements | 2:37 | |
| I’ll Be Here In the Morning | Jason Molina | 2:29 | |
| Airline To Heaven | Billy Bragg, Wilco | 4:50 | |
| My Flying Saucer | Billy Bragg, Wilco | 1:44 | |
| Sweet Illusions | Ryan Adams & The Cardinals | 5:01 | |
| Be Kind To The Boy On The Road | Billy Bragg, Wilco | 3:42 | |
| The Ballad Of Carol Lynn | Whiskeytown | 3:04 | |
| Magnolia Mountain | Ryan Adams & The Cardinals | 5:51 | |
| When The Roses Bloom Again | Billy Bragg, Wilco | 4:07 | |
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | |
| Strawberry Blonde | Ron Sexsmith | 3:41 | |
| Ought To Be Satisfied Now | Billy Bragg, Wilco | 3:30 | |
| When I Get To The Border | Richard & Linda Thompson | 3:27 | |
| Give Me A Nail | Billy Bragg, Wilco | 1:38 | |
| Let It Ride | Ryan Adams & The Cardinals | 3:23 | |
| Cold & Bitter Tears | Ted Hawkins | 2:14 | |