| Ruby | Dave Rawlings Machine | 4:54 | |
| Lo-Fi | The Bottle Rockets | 3:20 | |
| Hold On I | Chris Smither | 4:03 | |
| Take It from Me | Andrew Combs | 4:17 | |
| Country Love | The Gourds | 2:43 | |
| Hurricane Party | James McMurtry | 5:56 | |
| Before I Go | John Hiatt | 3:34 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Watch Me Fall | Uncle Tupelo | 2:12 | |
| Earthly Justice | Western Centuries | 4:03 | |
| Cemetary Road | Fred Eaglesmith | 2:17 | |
| Levelland | James McMurtry | 5:23 | |
| Big Cheeseburgers and Good French Fries | Gurf Morlix | 2:51 | |
| Ten Miles Down the Nine Mile Road | Scott Miller | 4:13 | |
| Smile | The Bottle Rockets | 2:25 | |
| Uncle Lloyd | Darrell Scott | 4:11 | |
| Train to Jackson | Jeffrey Foucault | 4:17 | |
| Ghosts of Our Fathers | Otis Gibbs | 3:46 | |
| The Prettiest Thing | The Modern Don Juans, David Childers | 4:14 | |
| We Can't Make It Here | James McMurtry | 7:06 | |
| Annie | Yarn | 4:05 | |
| Unlock more with Songs Like X Pro |
| Cigarette Machine | Fred Eaglesmith | 4:31 | |
| Waltz About Whiskey | Watchhouse | 3:46 | |
| Knee Deep in the Wakarusa River | Chuck Mead | 3:29 | |
| Big River | Darrell Scott | 3:26 | |
| Dallas | The Flatlanders | 3:01 | |
| When The Wheels Touch Down | Wrinkle Neck Mules | 4:11 | |
| Love Is Just A Wrecking Ball | Del Barber | 4:20 | |
| Levelland | James McMurtry | 5:39 | |
| The Last Pharaoh | Dave Rawlings Machine | 3:37 | |
| Sometimes Dogs Bark at Nothing | JP Harris | 2:27 | |
| Hard to Be an Outlaw (feat. Willie Nelson) | Billy Joe Shaver, Willie Nelson | 3:06 | |
| Wishing All These Things Were New | Merle Haggard | 3:20 | |
| Forgotten Coast | James McMurtry | 3:34 | |
| Indianapolis | The Bottle Rockets | 3:32 | |
| Holy Water | Jonny Fritz | 2:40 | |
| Monster Truck | Ramsay Midwood | 3:30 | |
| West Texas Waltz | Joe Ely | 4:55 | |
| Who Carried You | Malcolm Holcombe | 3:31 | |
| Too Drunk To Dream | Whiskeytown | 2:53 | |
| Runnin’ Shine | Lukas Nelson and Promise of the Real | 3:22 | |
| I Want It So Bad | The Gourds | 3:37 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| Water In The Fuel | Fred Eaglesmith | 5:21 | |
| The Pugilist At 59 | Tom Russell | 4:29 | |
| Sangria Wine | Jerry Jeff Walker | 4:27 | |
| Half Ton Van | John R. Miller | 3:26 | |
| Excuse Me While I Break My Own Heart Tonight - Strangers Almanac Album Version | Whiskeytown | 3:14 | |
| Gallo Del Cielo - Live At Antone's, Austin, TX / January 22 & 23, 1999 | Joe Ely | 7:04 | |
