| Highway in the Wind | Arlo Guthrie | 2:41 | |
| Pack up Your Sorrows | Loudon Wainwright III, Iris DeMent | 2:44 | |
| The Trip | Dave Rawlings Machine | 10:55 | |
| Evona Darling | Linda Thompson, Teddy Thompson | 3:19 | |
| Fading Fast | Iain Matthews, Elliott Murphy | 3:54 | |
| Do La Lay | Jesse Winchester | 1:53 | |
| Little Ann | The Felice Brothers | 3:23 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| I'm Not Gonna Cry | Loudon Wainwright III | 2:06 | |
| Stay Down, Man | Dan Reeder | 1:54 | |
| The Way I Love Her | Bap Kennedy | 3:30 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| Would You Like To Learn To Dance | Steve Goodman | 4:01 | |
| Dandelion Wine | Ron Sexsmith | 3:29 | |
| The Whole Night Sky | Bruce Cockburn | 3:54 | |
| Last Train | Arlo Guthrie | 3:06 | |
| Katie Dear | The Felice Brothers | 3:58 | |
| Almost Always Wrong | Bap Kennedy | 2:19 | |
| Red Guitar | Loudon Wainwright III | 1:48 | |
| I'm a Mess | Nick Lowe | 3:10 | |
| Don't Say Goodbye | Buddy & Julie Miller, Buddy Miller, Julie Miller | 5:10 | |
| Unlock more with Songs Like X Pro |
| When The Night Was Young | Robbie Robertson | 5:04 | |
| All The Lilacs In Ohio | John Hiatt, Jerry Douglas | 3:29 | |
| Mama You've Been On My Mind / A Fraction of Last Thoughts on Woody Guthrie | Jack Johnson | 4:21 | |
| New York City's Killing Me (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 4:13 | |
| Across The River | Alejandro Escovedo | 5:20 | |
| New York | The Milk Carton Kids | 3:32 | |
| Talk to Me of Mendocino | Kate & Anna McGarrigle | 3:10 | |
| Take The Long Way | Po' Girl, C.R. Avery | 5:32 | |
| Railroad Man | Eels | 4:16 | |
| Our Town | Iris DeMent | 5:00 | |
| Old Before Your Time (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 4:03 | |
| Human Thing | The Be Good Tanyas | 4:08 | |
| Matapedia | Kate & Anna McGarrigle | 4:53 | |
| Tired of This Life | Dawn Landes | 3:04 | |
| The Beast in Me | Nick Lowe | 2:28 | |
| Promises to Keep | Eliza Gilkyson | 4:23 | |
| Both Sides Now | Dave Van Ronk | 5:14 | |
| Saw Your Name in the Paper | Loudon Wainwright III | 2:12 | |
| I've Fallen In Love | Bap Kennedy | 3:21 | |
| Pale Moon | Shannon McNally, Neal Casal | 4:39 | |
| Old Friends | Chuck Prophet | 3:56 | |
| Steal Your Heart Away | Watkins Family Hour, Sara Watkins, Sean Watkins | 2:45 | |
| Bird On the Wire | Tim Hardin | 5:27 | |
| A Thing Called Rain | Jackie Greene | 4:35 | |
| Your Love Is My Rest | John Hiatt | 4:34 | |
| Longest Days | John Mellencamp | 3:10 | |
| There's A Rhythm | Ron Sexsmith | 3:25 | |
| Inn Town | Whiskeytown | 5:51 | |
