| Jealous Guy | Hurray For The Riff Raff | 3:27 | |
| Calm Before the Storm | Eliza Gilkyson | 3:50 | |
| White Girl | The Milk Carton Kids | 3:44 | |
| History of Lovers | Calexico, Iron & Wine | 3:09 | |
| Only One and Only | Gillian Welch | 5:33 | |
| Harvest Moon Blues | Zoe Muth and the Lost High Rollers | 4:46 | |
| Brokedown Palace | Watkins Family Hour, Sara Watkins, Sean Watkins | 4:09 | |
| Acid Tongue | Jenny Lewis | 3:50 | |
| Loretta | Aoife O'Donovan, Taylor Ashton | 2:28 | |
| Over the Red Cedar | Charlie Parr | 4:19 | |
| Hymn #35 | Joe Pug | 3:11 | |
| Whiskey Poet | Corinne West, Kelly Joe Phelps | 4:41 | |
| Crop Comes In | Chatham County Line | 4:23 | |
| What It Means | Drive-By Truckers | 6:25 | |
| Swimming Song | Kate & Anna McGarrigle | 2:29 | |
| Green, Green Rocky Road | Dave Van Ronk | 3:42 | |
| I Got a Pig in a Pen | Ralph Stanley, Gillian Welch, Dave Rawlings | 1:58 | |
| Rock of Ages | Gillian Welch | 3:08 | |
| Deer Creek Canyon | Sera Cahoone | 3:18 | |
| King Cotton | The Secret Sisters | 3:12 | |
| Morning Trian | David Francey | 2:28 | |
| Unlock more with Songs Like X Pro |
| Hey Stranger | Watchhouse | 3:27 | |
| Señor (Tales of Yankee Power) | Willie Nelson, Calexico | 5:17 | |
| Strange Isabella | Gillian Welch | 3:50 | |
| Better Times Will Come | Diana Jones | 2:53 | |
| Keep It Clean | Willie Watson | 3:35 | |
| Let the Mystery Be | Iris DeMent | 2:46 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| The Battle (feat. Ryan Adams) | Caitlin Cary, Ryan Adams | 3:00 | |
| Mississippi | The Secret Sisters | 4:22 | |
| Table For One | Courtney Marie Andrews | 3:59 | |
| Must Be the Whiskey | Chip Taylor, Carrie Rodriguez | 3:59 | |
| Where I'm From | Shelby Lynne | 3:50 | |
| Ain't No Grave | Crooked Still | 3:21 | |
| Travelers Paradise | The Cactus Blossoms | 2:58 | |
| Soul Of A Man | Ollabelle | 3:59 | |
| Conversation with Death | Brooke Buckner, George Buckner, David Rawlings, Gillian Welch | 6:16 | |
| Katie Cruel | Karen Dalton | 2:22 | |
| It Hurts Me Too | Karen Dalton | 3:07 | |
| Please, Please Baby | Reckless Kelly, Rhonda Vincent, Gillian Welch, Sara Evans, Bonnie Bramlett, The Blazers, Pete Drodge | 2:43 | |
| Magnolia Mountain | Ryan Adams & The Cardinals | 5:51 | |
| The Banks of the Leopold Canal | The Deep Dark Woods | 6:08 | |
| May You Never | John Martyn | 3:40 | |
| The Maker | Willie Nelson | 5:08 | |
| It'll Take A Long Time | Sandy Denny | 5:14 | |
| Rich Woman | Robert Plant, Alison Krauss | 4:03 | |
| All The Right Reasons | The Jayhawks | 3:24 | |
| Mixtape | Tift Merritt | 3:18 | |
| Biloxi | Ted Hawkins | 4:41 | |
