| Winner's Casino | Richmond Fontaine | 4:06 | |
| Sandusky | Uncle Tupelo | 3:43 | |
| Dry Lightning | Bruce Springsteen | 3:30 | |
| Lost In The Backyard | James McMurtry | 4:11 | |
| Western Sky | Freedy Johnston | 4:29 | |
| Lost Love | Golden Smog | 3:00 | |
| Blue Canoe | Blue Mountain | 4:39 | |
| After the Rain | Chuck Prophet | 3:35 | |
| Rocky World | Daniel Lanois | 2:55 | |
| The Whole Night Sky | Bruce Cockburn | 3:54 | |
| Barstool Boys | Marah | 3:04 | |
| Designs on You | Old 97's | 3:48 | |
| The Late John Garfield Blues | Sara Watkins | 4:06 | |
| Unwed Fathers (feat. Liz Isenberg) | Deer Tick, Liz Isenberg | 3:39 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| The El | Rhett Miller | 3:09 | |
| Color of a Lonely Heart Is Blue | Old 97's | 5:51 | |
| Hard Bargain | Ron Sexsmith | 3:12 | |
| Mama You've Been On My Mind / A Fraction of Last Thoughts on Woody Guthrie | Jack Johnson | 4:21 | |
| Please Stay | Warren Zevon | 3:34 | |
| 14 Days | Nick Lowe | 2:57 | |
| Unlock more with Songs Like X Pro |
| Don't Say Goodbye | Buddy & Julie Miller, Buddy Miller, Julie Miller | 5:10 | |
| Next Best Western | Richard Shindell | 4:17 | |
| Wink | Blue Mountain | 3:17 | |
| We Used to Think the Freeway Sounded Like a River | Richmond Fontaine | 3:26 | |
| Everybody's Hurting | Jakob Dylan | 3:40 | |
| How Far We've Come | Dawes | 2:59 | |
| Last Night Of The World | Bruce Cockburn | 4:51 | |
| I Forgive It All | Mudcrutch | 4:13 | |
| Red Dress | Israel Nash | 4:07 | |
| No Matter What You Do (Jakob Dylan & Regina Spektor) | Echo In The Canyon | 2:47 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Question | Old 97's | 2:15 | |
| Different When It Comes To You | Bruce Cockburn | 2:57 | |
| Nothing's Gonna Change the Way You Feel About Me Now | Justin Townes Earle | 3:04 | |
| Screen Door | Uncle Tupelo | 2:42 | |
| Looking Forward to Seeing You | Golden Smog | 2:47 | |
| A Thing Called Rain | Jackie Greene | 4:35 | |
| Nevada, California | The Jayhawks | 4:05 | |
| Sunrise Always Listens | Paul Westerberg | 4:19 | |
| Whispering Pines | Jakob Dylan | 4:05 | |
| Either Side Of The Same Town | Elvis Costello & The Imposters | 3:59 | |
| Some Other Time, Some Other Place | Peter Wolf | 3:49 | |
| When I Cross Over | Tift Merritt | 6:32 | |
| Madman | The Jayhawks | 4:02 | |
| Hoping Machine | Jay Farrar, Will Johnson, Anders Parker, Yim Yames | 4:52 | |
| The Right Place | Monsters Of Folk | 3:48 | |
| Fireflies | Rhett Miller, Rachael Yamagata | 4:07 | |
| Farewell Angelina - 1997/Live In Bellmont Mall Studios | John Mellencamp | 4:35 | |
