| Isadora Duncan | Vic Chesnutt | 4:35 | ||
| Baltimore Oriole | Judy Henske | 2:24 | ||
| If Only You Were Lonely - Twin Tone Single Version | The Replacements | 2:37 | ||
| You Never Wanted Me | Jackson C. Frank | 3:07 | ||
| The Man Who Couldn't Cry | Loudon Wainwright III | 6:15 | ||
| Reasons To Quit | Phosphorescent | 3:13 | ||
| Little Ann | The Felice Brothers | 3:23 | ||
| Suffering Jukebox | Silver Jews | 4:21 | ||
| Acuff-Rose | Uncle Tupelo | 2:35 | ||
| Like a Monkey in a Zoo | Daniel Johnston | 3:26 | ||
| Make Me a Pallet on Your Floor | Gillian Welch | 2:46 | ||
| The Beehive State | Harry Nilsson | 2:07 | ||
| Canadee-I-O | Nic Jones | 5:55 | ||
| Polly Vaughn | Tia Blake | 4:22 | ||
| Can't Get Away from My Love | Jackson C. Frank | 2:50 | ||
| The Tea Song | Michael Hurley | 7:28 | ||
| New Paint | Loudon Wainwright III | 3:00 | ||
| Banjo Moon | Greg Brown | 7:10 | ||
| Illegal Smile | John Prine | 3:13 | ||
| I Think Too Much of You | The Flatlanders | 2:12 | ||
| I Don't Like The Man I Am | Pete Molinari | 3:34 | ||
| Unlock more with Songs Like X Pro | ||||
| Life’s Greatest Fool | Gene Clark | 4:42 | ||
| Go 'Way from My Window | John Jacob Niles | 2:09 | ||
| I'm a Man of Constant Sorrow | Tia Blake | 2:50 | ||
| I Am a Pilgrim | The Byrds | 3:39 | ||
| The Mountain Low | Palace Music | 2:44 | ||
| One Season | The Roches | 4:42 | ||
| Luxury Liner | The International Submarine Band | 2:48 | ||
| Motel Blues | Loudon Wainwright III | 2:47 | ||
| In the Pines | Billy Bragg, Joe Henry | 3:31 | ||
| When I Leave Berlin | Wizz Jones, Lazy Farmer | 3:18 | ||
| The Dark-Eyed Sailor | Steeleye Span | 5:58 | ||
| The Way It Goes | Gillian Welch | 4:01 | ||
| Going To San Diego | Allen Ginsberg | 4:16 | ||
| (I Was Drunk At The) Pulpit | Palace Brothers | 3:51 | ||
| The French Inhaler | Warren Zevon | 3:32 | ||
| Drive Like I Never Been Hurt | Ry Cooder | 4:07 | ||
| Elvis Presley Blues | Gillian Welch | 4:56 | ||
| Fallin' Rain | Link Wray | 3:45 | ||
| The American Dreamer | Gene Clark | 1:54 | ||
| Wheels | The Flying Burrito Brothers | 3:02 | ||
| Dallas | Jimmie Dale Gilmore, The Flatlanders | 2:48 | ||
| Be Not So Fearful | Bill Fay | 2:44 | ||
| I'll Keep It With Mine | Nico | 3:17 | ||
| A Heart Needs A Home | Shawn Colvin, Loudon Wainwright III | 3:35 | ||
| Reno Nevada | Mimi And Richard Farina | 3:12 | ||
| Ingrid Bergman | Billy Bragg, Wilco | 1:50 | ||
| We Sing Hallelujah | Richard & Linda Thompson | 2:52 | ||
| Pay Day | Mississippi John Hurt | 4:21 | ||
