| City of Immigrants (with Forro in the Dark) | Steve Earle | 4:18 | |
| Fugitive | Indigo Girls | 4:35 | |
| (Don't Go Back To) Rockville | 10,000 Maniacs | 4:39 | |
| Lillian, Egypt | Josh Ritter | 3:24 | |
| Down By The Henry Moore | Blackie & The Rodeo Kings | 4:02 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| The Asp and the Albatross | Freakwater | 3:10 | |
| The Poet Game | Greg Brown | 5:32 | |
| A Robin or A Wren | Jeff Tweedy | 2:48 | |
| Pushed Her Down | The Gourds | 3:11 | |
| What's One More Time | Lori McKenna | 4:03 | |
| Poor, Poor LA | Tim Easton | 3:49 | |
| It Wasn't Me | Jenny Lewis, The Watson Twins | 4:12 | |
| Oyster and Pearl | Amy Ray, Phil Cook, Brad Cook, Justin Vernon | 4:00 | |
| Pulling On A Line | Great Lake Swimmers | 3:19 | |
| When the Night Comes Falling from the Sky | Lucius | 6:20 | |
| Radio King | Golden Smog | 3:09 | |
| One Fast Move or I'm Gone | Jay Farrar, Benjamin Gibbard | 4:15 | |
| Southern Rain | Cowboy Junkies | 4:50 | |
| Cigarettes Coffee and Booze | The Minus 5 | 4:24 | |
| Rex's Blues | Son Volt - Jay Farrar & Kelly Willis | 4:40 | |
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| I Understand Now | Patterson Hood | 3:22 | |
| The Losing End Again | Neal Casal | 3:12 | |
| This Wheel’s on Fire | Guster | 3:24 | |
| The War After the War | Mary Gauthier | 3:44 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| If I've Only One Time Askin' | Daniel Romano | 2:54 | |
| Half A Million Miles | The Kennedys | 3:45 | |
| Losing Battles | Josh Ritter | 4:22 | |
| Get This Right | Lilly Hiatt | 3:29 | |
| Wichita Ain't so Far Away | The Delines | 2:31 | |
| Should've Been in Love - 2017 Remaster | Wilco | 3:35 | |
| Where I'm From | Shelby Lynne | 3:50 | |
| Everything Is Your Fault | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:14 | |
| Lost Without You | Rhett Miller | 4:54 | |
| Sure Feels Good Anyway | Amy Ray | 4:30 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| Sure As Shit | Kathleen Edwards | 4:09 | |
| Lebanon, Tennessee | Ron Sexsmith | 2:57 | |
| Avenues | Whiskeytown | 2:31 | |
| Pink Champagne | Kathleen Edwards | 5:09 | |
| Dancing With The Women At The Bar | Whiskeytown | 4:38 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Westby | Kathleen Edwards | 2:26 | |
| If It Were Up to Me | Cheryl Wheeler | 3:08 | |
| Strangers | Golden Smog | 3:19 | |
| Maria | Kathleen Edwards | 3:45 | |
| Old L.A. | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 3:03 | |
| Mint | Kathleen Edwards | 4:51 | |