| That Bird Has a Broken Wing | Sun Kil Moon | 2:30 | |
| Roger Ebert | Clem Snide | 2:53 | |
| Day After Tomorrow | Tom Waits | 5:58 | |
| Young at Heart | Dan Reeder | 1:48 | |
| What Does It Matter Now? | Micah P. Hinson | 4:35 | |
| Hometown Hero | The Felice Brothers | 3:38 | |
| Pushkin | Palace Brothers | 2:52 | |
| Oh, My Girl | Jesse Sykes & The Sweet Hereafter | 4:38 | |
| Passage's End | Jesca Hoop | 4:37 | |
| When I Ran off and Left Her | Vic Chesnutt | 2:54 | |
| Wonderous Love (Lissy’s Sessions) | Songs: Ohia, Jason Molina | 2:20 | |
| Blue and Wonder | Richard Buckner | 3:47 | |
| Slow Joke Grin | Laura Gibson | 3:25 | |
| That’s Just the Way That I Feel | Purple Mountains | 3:23 | |
| Beware of Darkness | Antietam, Will Oldham, Todd Brashear | 3:50 | |
| The Dark Don’t Hide It | Kevin Morby, Waxahatchee | 4:22 | |
| Ballad of Lonesome Hunter | Timber Timbre | 2:08 | |
| The Roving | Bonny Light Horseman, Eric D. Johnson, Josh Kaufman, Anaïs Mitchell | 4:20 | |
| Suffering Jukebox | Silver Jews | 4:21 | |
| Didn't It Rain | Songs: Ohia, Jason Molina | 7:52 | |
| You Will Miss Me When I Burn | Palace Brothers | 3:18 | |
| Unlock more with Songs Like X Pro |
| Tumble in the Wind (Version 2) | Jackson C. Frank | 3:07 | |
| The Sway | Joan Shelley | 3:22 | |
| Bonny Light Horseman | Bonny Light Horseman, Eric D. Johnson, Josh Kaufman, Anaïs Mitchell | 4:30 | |
| Darkness and Cold | Purple Mountains | 3:58 | |
| These Rocks | Phosphorescent | 4:26 | |
| That Girl From Brownsville Texas | Jim White | 6:22 | |
| Rooftops | Gambles | 3:01 | |
| Time Forgot (To Change My Heart) | Daniel Romano | 4:00 | |
| The Way You Smile | Blaze Foley | 3:14 | |
| Bug | Vic Chesnutt | 3:17 | |
| Maybe She | Arthur Russell | 2:51 | |
| Treasure | Aldous Harding | 4:11 | |
| Leave It Behind (feat. Will Oldham) | Homesick Hank, Will Oldham | 4:19 | |
| Jane Jane | Bonny Light Horseman, Eric D. Johnson, Josh Kaufman, Anaïs Mitchell | 3:06 | |
| A Certain Kind Of Memory | Kacy & Clayton | 4:44 | |
| Admiral Fell Promises | Sun Kil Moon | 3:51 | |
| The Night Shift Lullaby | Magnolia Electric Co., Jason Molina | 4:33 | |
| Southern United States | Leif Vollebekk | 4:07 | |
| The Gray Tower | Songs: Ohia, Jason Molina | 4:39 | |
| When the Sun Comes Up | Bert Jansch, Beth Orton | 3:54 | |
| Glenn Tipton | Sun Kil Moon | 4:16 | |
| You Are Never Alone | Vic Chesnutt | 5:45 | |
| Empty Hearted Town | Warren Zevon | 3:06 | |
| Sharp Cutting Wings (Song to a Poet) | Lucinda Williams | 3:35 | |
| The Mating of the Doves | The Felice Brothers | 3:48 | |
| All These Vicious Dogs | Will Oldham | 2:23 | |
| Call Me A Liar | Will Oldham | 4:20 | |
| Torn And Brayed | Matt Sweeney, Will Oldham | 3:18 | |
