| That's the Way That the World Goes 'Round | John Prine | 3:20 | |
| Wildflowers | Tom Petty | 3:10 | |
| Colorado | Stephen Stills | 2:52 | |
| Yes I Guess They Oughta Name a Drink After You | John Prine | 2:10 | |
| Bears | Lyle Lovett | 3:05 | |
| Glad and Sorry | Faces | 3:06 | |
| It Ain't Over Yet | Rodney Crowell, Rosanne Cash, John Paul White | 5:14 | |
| Romeo's Tune | Steve Forbert | 3:32 | |
| Caravan - 2013 Remaster | Van Morrison | 5:00 | |
| Dead Flowers | Townes Van Zandt | 4:47 | |
| Rapid Roy (The Stock Car Boy) | Jim Croce | 2:46 | |
| Poor Poor Pitiful Me | Warren Zevon | 3:05 | |
| Keep 'Em on They Toes | Brent Cobb | 2:43 | |
| Fraulein (feat. Tyler Childers) | Colter Wall, Tyler Childers | 2:23 | |
| Live Forever | Billy Joe Shaver | 2:49 | |
| Codeine | Trampled by Turtles | 3:09 | |
| Thirteen Silver Dollars | Colter Wall | 2:30 | |
| Casey Jones - 2013 Remaster | Grateful Dead | 4:25 | |
| Lake Marie | John Prine | 6:00 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| My Sweet Annette | Drive-By Truckers | 3:51 | |
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| Heard It in a Love Song | The Marshall Tucker Band | 4:57 | |
| Box #10 | Jim Croce | 2:27 | |
| I'll Be Here in the Morning | Townes Van Zandt | 3:00 | |
| The Great Joe Bob (a Regional Tragedy) | Terry Allen | 4:42 | |
| Quiet Man | John Prine | 2:52 | |
| Snakes and Waterfalls | Nick Shoulders | 4:02 | |
| I Hope That I Don't Fall In Love With You | Tom Waits | 3:53 | |
| Dust in a Baggie | Billy Strings | 2:54 | |
| Bob | Drive-By Truckers | 2:15 | |
| Desperado | The Cactus Blossoms | 2:46 | |
| Just Us Kids | James McMurtry | 5:08 | |
| Little Martha | Allman Brothers Band | 2:07 | |
| Shady Grove | Doc Watson | 2:59 | |
| Out In The Woods | Leon Russell | 3:37 | |
| Walk Between The Raindrops | James McMurtry | 3:24 | |
| Where Have All The Average People Gone - Single Version | Roger Miller | 3:01 | |
| Melissa | Allman Brothers Band | 3:55 | |
| Blue | The Jayhawks | 3:09 | |
| Way Over Yonder In The Minor Key | Billy Bragg, Wilco | 4:06 | |
| Sin City | The Flying Burrito Brothers | 4:09 | |
| Set Me Down On A Cloud | Lukas Nelson and Promise of the Real, Lucius | 7:16 | |
| Ramblin' Man | Allman Brothers Band | 4:48 | |
| Gone Gone Gone (Done Moved On) | Robert Plant, Alison Krauss | 3:32 | |
| The Weight - Remastered 2000 | The Band | 4:34 | |
| Drifters Wife | J.J. Cale | 1:40 | |
| The Weary Kind | Ryan Bingham | 4:18 | |
| Don't Make Me Explain It | Ted Hawkins | 2:37 | |
| Garden Party | Ricky Nelson, The Stone Canyon Band | 3:49 | |