| Winsome Smile | Chris Smither | 3:34 | |
| Tecumseh Valley | Jason Isbell, Elizabeth Cook | 4:40 | |
| Speed Of The Sound Of Loneliness | John Prine | 3:28 | |
| Windfall - 2015 Remaster | Son Volt | 2:59 | |
| Sugaree | Jerry Garcia | 5:52 | |
| Mexican Home (feat. John Prine) | Chris Knight, John Prine | 5:05 | |
| Before I Go | John Hiatt | 3:34 | |
| There She Goes | John Prine | 3:24 | |
| Memories | Swamp Dogg, John Prine | 4:47 | |
| Caroline (feat. Belle Plaine) | Colter Wall, Belle Plaine | 2:53 | |
| Life Ain't Fair and the World Is Mean | Sturgill Simpson | 2:06 | |
| Midnight Run | Charley Crockett | 3:51 | |
| The Swimming Song | Loudon Wainwright III | 2:27 | |
| Dreamsicle | Jason Isbell and the 400 Unit | 3:44 | |
| Grandpa Was a Carpenter | John Prine | 2:52 | |
| Big City | Merle Haggard | 2:59 | |
| Over the Red Cedar | Charlie Parr | 4:19 | |
| All Around You | Sturgill Simpson | 3:09 | |
| She's All I Got | Johnny Paycheck | 2:56 | |
| 24 Frames | Jason Isbell | 3:13 | |
| Keep It Clean | Willie Watson | 3:35 | |
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| Knockin' on Your Screen Door | John Prine | 2:19 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Cigarette Machine | Fred Eaglesmith | 4:31 | |
| Lonesome L.A. Cowboy | New Riders of the Purple Sage | 4:03 | |
| Lovin' in My Baby's Eyes | Taj Mahal | 2:40 | |
| East Indian Princess | Loudon Wainwright III | 2:56 | |
| Pretty Good | John Prine | 3:36 | |
| At Your Window | Trampled by Turtles | 3:24 | |
| Birmingham | Shovels & Rope | 4:00 | |
| No Depression | Uncle Tupelo | 2:20 | |
| I Gotta Get Drunk (with Willie Nelson) | George Jones, Willie Nelson | 2:10 | |
| One Red Rose | Iris DeMent | 3:07 | |
| I Don't Mind | Sturgill Simpson | 4:29 | |
| Codeine | Jason Isbell and the 400 Unit | 5:44 | |
| Blue | The Jayhawks | 3:09 | |
| Garden Party | Ricky Nelson, The Stone Canyon Band | 3:49 | |
| Jealous Man | Hoyt Axton | 1:20 | |
| Beaumont | Hayes Carll | 3:27 | |
| Postcards From Hell | The Wood Brothers | 4:44 | |
| Hang Me, Oh Hang Me | Dave Van Ronk | 3:10 | |
| Fox On The Run - Single Version | Tom T. Hall | 2:05 | |
| Northeast Texas Women | Willis Alan Ramsey | 5:51 | |
| Taking Water | Billy Strings | 4:08 | |
| Don't Come Home A-Drinkin' (With Lovin' On Your Mind) | Loretta Lynn | 2:06 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| Drifters Wife | J.J. Cale | 1:40 | |
| That's How I Got To Memphis | Tom T. Hall | 3:02 | |
| Lovin' In My Baby's Eyes | Leftover Salmon | 2:56 | |