| People My Age | John Gorka | 2:16 | |
| Watching the Wheels | Chatham County Line | 3:53 | |
| Laughing River | Greg Brown | 6:23 | |
| South | Blackie & The Rodeo Kings | 4:24 | |
| We Can't Make It Here | James McMurtry | 7:06 | |
| Johnny And June | Truckstop Honeymoon | 3:02 | |
| Man of God | Eliza Gilkyson | 4:27 | |
| Emmy-Lou | Dustin Bentall & The Smøkes | 3:02 | |
| I Don't Work in a Bank | Joe Pug | 1:35 | |
| If I Could Only See | Billy T Band, Fats Kaplin | 3:42 | |
| Worth Dyin' For | Gurf Morlix | 4:42 | |
| Rambling, Gambling Willie | The Lonely Heartstring Band | 3:27 | |
| My Shits Fucked Up | Kinky Friedman | 3:13 | |
| She Came on to Me | John R. Butler | 4:18 | |
| Dog - Audiotree Live Version | The Bottle Rockets, Audiotree | 2:21 | |
| I'd Be Missing You | Kevin Welch | 3:06 | |
| Come See About Me | Tom Rush | 2:50 | |
| Spittin’ On Fire | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:05 | |
| You Don't Know Me | Kieran Kane, Rayna Gellert | 2:16 | |
| Bosler | Jalan Crossland | 3:50 | |
| It Was a Train | Otis Gibbs | 3:10 | |
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| Compadres In The Old Sierra Madre | The Waybacks | 5:12 | |
| Blue Ridge Parkway | The Mallett Brothers Band | 2:23 | |
| Backwater | Big Smith | 4:34 | |
| I Can't Wait | Kieran Kane, Kevin Welch, Fats Kaplin | 3:31 | |
| I Don't Want To Have A Nice Day | Greg Brown | 3:28 | |
| Welding Burns | Rod Picott | 3:43 | |
| Streets of Love | Kevin Welch | 3:55 | |
| You're Still Around | Kristi Rose, Fats Kaplin | 3:16 | |
| Firestorm | Danny Schmidt | 3:46 | |
| Tennessee Tobacco | Danny Michel | 3:06 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Ditch | Sam Baker | 1:56 | |
| Jesus & Elvis | Greg Brown | 3:38 | |
| You Gotta Have a Dance / St. James Hospital | Tom Russell, Fats Kaplin, Moses Clear Rock Platt | 2:41 | |
| The Mother Road | Kevin Welch | 4:21 | |
| The Devil's Paintbrush Road | The Wailin' Jennys | 3:47 | |
| You Don't Know How It Feels | Chatham County Line | 4:14 | |
| Lost John Dean | Kieran Kane, Kevin Welch, Fats Kaplin | 3:26 | |
| Colorado Sky | Cristina Vane | 3:08 | |
| Thank God for the Road | The Flatlanders | 5:00 | |
| Loser | The Cleverlys | 4:19 | |
| Another Free Woman | Blackie & The Rodeo Kings, Sara Watkins | 3:30 | |
| Waterbound | Dirk Powell | 2:53 | |
| Nine Inch Nails | Ridley Bent | 3:56 | |
| Highland County Boy | Scott Miller | 2:44 | |
| Bottom Of The World | Alejandro Escovedo | 3:04 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| Black Sheep | Blackie & The Rodeo Kings, Serena Ryder | 5:28 | |