| Red Dress | Israel Nash | 4:07 | |
| Just Like You | Gill Landry | 4:45 | |
| Wildwood | Chatham County Line | 3:06 | |
| Come On Over My House | David Rawlings | 3:42 | |
| Where Is Maria | Greg Brown | 5:21 | |
| Merrimac County | Tom Rush | 2:51 | |
| Tell Me A Story | Po' Girl | 3:13 | |
| Shy Star | Ray Bonneville | 4:04 | |
| Give Me a Sad Song | Linda Thompson | 3:56 | |
| Dream Café | Greg Brown | 5:57 | |
| King Cotton | The Secret Sisters | 3:12 | |
| Only Fooling | Teddy Thompson, Kelly Jones | 2:45 | |
| The Prettiest Thing | The Modern Don Juans, David Childers | 4:14 | |
| Joe Hill's Ashes | Otis Gibbs | 3:26 | |
| Chip of a Star | Chatham County Line | 4:30 | |
| Who Do You Think You're Fooling | Greg Brown | 5:53 | |
| Series of Closin' Doors | Gurf Morlix | 4:33 | |
| New York City's Killing Me (with The Pariah Dogs) | Ray LaMontagne, The Pariah Dogs | 4:13 | |
| East of Eden | Tom Rush | 3:29 | |
| Holy Rollers For Love | Jakob Dylan | 3:55 | |
| Where Are You Going When You're Gone | Greg Brown | 3:44 | |
| Unlock more with Songs Like X Pro |
| Never Cry Again | John Fullbright | 4:14 | |
| I'll Trade You Money for Wine | Robbie Fulks | 4:33 | |
| Jerusalem Tomorrow | David Olney | 5:09 | |
| The Way I Love Her | Bap Kennedy | 3:30 | |
| I've Been Gone | Zoe Muth and the Lost High Rollers | 4:28 | |
| Whistle on Occasion (feat. Chuck Prophet) | Kim Richey, Chuck Prophet | 2:36 | |
| Restless Farewell | Mark Knopfler | 5:51 | |
| Katie Dear | The Felice Brothers | 3:58 | |
| What Do We Do Now | John Hiatt | 2:58 | |
| They Call Me Hank | Greg Trooper | 4:48 | |
| Driftless | Greg Brown | 3:01 | |
| Mr. Bojangles | David Bromberg | 7:28 | |
| If You Knew My Mind | Grayson Capps | 3:03 | |
| Paper Gown | Caroline Herring | 4:31 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Too Long (I've Been Gone) | Dom Flemons | 2:53 | |
| Moonshine | Luther Dickinson | 4:40 | |
| Across the Great Divide | Kate Wolf | 4:14 | |
| Rings | Leo Kottke, Mike Gordon | 4:30 | |
| Who Carried You | Malcolm Holcombe | 3:27 | |
| Alright Alright | Birds of Chicago | 4:02 | |
| Oh, Sister [Feat. Courtney Marie Andrews] | Logan Ledger, Courtney Marie Andrews | 3:40 | |
| Heart A Mine | Blackie & The Rodeo Kings, Mary Margaret O'Hara | 3:56 | |
| Sugar Mama | The Deep Dark Woods | 2:39 | |
| My Heart Is Broken | Ryan Adams & The Cardinals | 2:11 | |
| You Can't Fail Me Now | Loudon Wainwright III | 3:45 | |
| Afraid | Ted Hawkins | 4:36 | |
| Black Sheep | Blackie & The Rodeo Kings, Serena Ryder | 5:28 | |
