| Poor Side of Town | Doug Seegers | 5:03 | |
| Whiskey Angel | The Black Lillies | 4:52 | |
| It's Not Easy | Teddy Thompson | 2:35 | |
| Blue Is My Heart | Holly Williams | 2:42 | |
| She's Leaving in the Morning | Zephaniah OHora | 3:08 | |
| Time Stands Still | Chris Smither | 3:45 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| Sweet Spot | Tift Merritt | 2:50 | |
| The Way I Love Her | Bap Kennedy | 3:30 | |
| If I Can't Trust You with a Quarter (How Can I Trust You with My Heart?) | Zoe Muth and the Lost High Rollers | 5:07 | |
| Nothing's Gonna Change the Way You Feel About Me Now | Justin Townes Earle | 3:04 | |
| Your Lonely Heart | Carrie Rodriguez | 2:58 | |
| Shelly's Winter Love | Bill Kirchen, Nick Lowe, Paul Carrack | 4:31 | |
| Oh, What A Feeling | Teddy Thompson | 2:39 | |
| Emerald Street | Eliza Gilkyson | 3:45 | |
| In My Dreams | Sam Lewis | 3:20 | |
| Wake Me in Wyoming | Whitney Rose | 3:26 | |
| Kansas | Fred Eaglesmith | 3:44 | |
| Here I Am Broken Hearted (feat. Teddy Thompson) | Linda Thompson, Teddy Thompson | 4:19 | |
| Make a Wish on Me - Commentary | Kelly Jones, Teddy Thompson | 0:37 | |
| You're Still On My Mind | Carrie Rodriguez | 2:56 | |
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| Life is Fine | Tom Rush | 3:39 | |
| Hey Little Darlin' | Zoe Muth | 3:30 | |
| Hearts Overflowing | Jonathan Edwards | 3:55 | |
| Tear My Stillhouse Down | Gillian Welch | 4:32 | |
| Millionaire | Kevin Welch | 3:59 | |
| High Class City Girl from the Country | Zephaniah OHora | 3:42 | |
| You're Through Fooling Me | Patty Loveless | 2:05 | |
| Gospel Plow | Elizabeth Cook | 2:54 | |
| It Won't Be Long Now | Linda Thompson | 2:37 | |
| Fall into the Night | Tom Rush | 3:55 | |
| One More Dollar | Gillian Welch | 4:35 | |
| Winsome Smile | Chris Smither | 3:34 | |
| Every Pilgrim Needs a Highway | Craig Market, Thomm Jutz | 3:32 | |
| Only Fooling - Commentary | Kelly Jones, Teddy Thompson | 1:25 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Learning How to Love Him | Amanda Anne Platt & the Honeycutters | 4:16 | |
| Never Knew You Loved Me Too | Teddy Thompson, Kelly Jones | 2:32 | |
| Hiway 9 | Eliza Gilkyson | 4:17 | |
| Christchurch Woman | Justin Townes Earle | 4:11 | |
| Wildflowers | Chris Hillman | 2:51 | |
| Killing the Blues | Robert Plant, Alison Krauss | 4:15 | |
| Drinkin' Days | Slaid Cleaves | 4:25 | |
| Down Low | Teddy Thompson | 5:52 | |
| Racecar Joe | Slaid Cleaves | 2:40 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Touching Home | Teddy Thompson | 2:46 | |
| Two Angels | Peter Case | 4:32 | |
| Different Rivers | Chris Hillman | 3:10 | |
