| Jukebox | The Honeycutters | 4:36 | |
| First Air of Autumn | Drive-By Truckers | 3:30 | |
| New Damnation Alley | Malcolm Holcombe, Iris DeMent | 4:20 | |
| The Great Joe Bob (a Regional Tragedy) | Terry Allen | 4:42 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Hickory Wind | The Byrds | 3:31 | |
| Wonderful Life | The Felice Brothers | 4:02 | |
| Steel Rail Blues | Gordon Lightfoot | 2:49 | |
| You've Never Seen Me Cry | The Flatlanders | 2:17 | |
| The L&N Don't Stop Here Anymore | Billy Bragg, Joe Henry | 4:29 | |
| Old Shoes | Tom Waits | 4:25 | |
| Vinyl Records | Todd Snider | 2:29 | |
| L.A. County | Lyle Lovett | 3:19 | |
| The Rosarita Beach Cafe | Warren Zevon | 4:09 | |
| Irene Wilde | Alejandro Escovedo | 2:51 | |
| KC Moan | Billy Bragg, Joe Henry | 2:40 | |
| Our Town | Iris DeMent | 5:00 | |
| Taxes on the Farmer Feeds Us All | Ry Cooder | 3:56 | |
| Leaving El Paso | Tom Russell | 3:32 | |
| Same Old Stagolee | Justin Townes Earle | 3:41 | |
| She's Got a New Spell | Billy Bragg | 3:25 | |
| Unlock more with Songs Like X Pro |
| How Can I Miss You When You Won't Go Away | Dan Hicks & His Hot Licks | 2:39 | |
| Just Like That (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 3:30 | |
| Drunken Barber's Hand | Slaid Cleaves | 2:41 | |
| One Too Many Mornings | Joe Henry | 3:28 | |
| Stars in My Life | The Flatlanders | 3:20 | |
| Down to the Well | Kevin Gordon | 4:10 | |
| The Trip | Dave Rawlings Machine | 10:55 | |
| Walkin' to New Orleans | Gurf Morlix | 4:38 | |
| Land of the Bottom Line | John Gorka | 3:33 | |
| Talkin At The Texaco | James McMurtry | 4:10 | |
| Spanish Moss | Jackson C. Frank | 4:30 | |
| Tecumseh Valley | Jason Isbell, Elizabeth Cook | 4:40 | |
| Border Lord | Kris Kristofferson | 3:37 | |
| In the Pines | Billy Bragg, Joe Henry | 3:31 | |
| The Hula Hula Boys - 2007 Remaster | Warren Zevon | 3:02 | |
| Green, Green Rocky Road | Dave Van Ronk | 3:42 | |
| Just the Other Side of Nowhere | Kris Kristofferson | 3:36 | |
| Tell the Devil I'm Gettin' there as Fast as I Can | Ray Wylie Hubbard | 5:47 | |
| Don't Speak in English | Chip Taylor, Carrie Rodriguez | 4:01 | |
| Nobody Wants to Be You | Dan Reeder | 2:08 | |
| Raggy Levy | Jake Xerxes Fussell | 3:59 | |
| Please Be With Me | Cowboy | 3:42 | |
| Who's Gonna Build Your Wall? | Tom Russell | 3:46 | |
| False Hearted Lover Blues | Levon Helm | 3:29 | |
| Goin' Down To Memphis - Demo Version | John Martyn | 3:01 | |
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | |
| Esther | Ramsay Midwood | 4:37 | |
| Percy's Song | Fairport Convention | 6:52 | |
