| Chalk | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:40 | |
| Strange Faces | Daniel Romano | 3:00 | |
| Wondering How | Pieta Brown | 3:06 | |
| Magnolia Tree | Truckstop Honeymoon | 3:47 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| Tear Stained Eye - 2015 Remaster | Son Volt | 4:20 | |
| Wrecking Ball - Live | Old Crow Medicine Show, Gillian Welch, David Rawlings | 5:32 | |
| Radio King | Golden Smog | 3:09 | |
| When My Time Comes | Dawes | 5:08 | |
| The Ballad of Bitter Honey | Eef Barzelay | 3:34 | |
| California | Joni Mitchell | 3:50 | |
| To Be Young (Is To Be Sad, Is To Be High) | Dave Rawlings Machine | 3:48 | |
| Conversation with Death | Brooke Buckner, George Buckner, David Rawlings, Gillian Welch | 6:16 | |
| People Get Old | Lori McKenna | 3:42 | |
| Relatively Easy | Jason Isbell | 4:45 | |
| Kathy's Song | The Secret Sisters | 3:43 | |
| Something Less Than Something More | Caitlin Cary, Thad Cockrell | 5:08 | |
| Take 'Em Away | Old Crow Medicine Show | 3:34 | |
| Shake Sugaree | Elizabeth Cotten and Brenda Evans | 5:02 | |
| Hard On You | Daniel Romano | 3:27 | |
| I Don't Always Miss You | Dan Reeder | 2:31 | |
| Unlock more with Songs Like X Pro |
| If I Could Only Fly | Blaze Foley | 4:04 | |
| Short Haired Woman Blues | Dave Rawlings Machine | 6:43 | |
| If I Ever Was a Child | Wilco | 2:55 | |
| Two Time Loser | The Deep Dark Woods | 4:27 | |
| In Spite of Ourselves (feat. Iris DeMent) | John Prine, Iris DeMent | 3:33 | |
| Shady Grove | Jerry Garcia, David Grisman | 4:19 | |
| Walkin’ Back to Georgia | Jim Croce | 2:51 | |
| I'm On Fire | Town Mountain | 3:33 | |
| He's Fine | The Secret Sisters | 3:43 | |
| Green, Green Rocky Road | Dave Van Ronk | 3:42 | |
| Unknown Legend | Shovels & Rope, Shakey Graves | 4:28 | |
| Lovin' in My Baby's Eyes | Taj Mahal | 2:40 | |
| Look at Miss Ohio | Gillian Welch | 4:14 | |
| Down by the Water | Abigail Lapell | 2:55 | |
| How Quickly Your Heart Mends | Courtney Marie Andrews | 3:45 | |
| I Pity the Country | Willie Dunn | 2:55 | |
| Dreamsicle | Jason Isbell and the 400 Unit | 3:44 | |
| Tehachapi | Margo Cilker | 3:07 | |
| My Sweet Annette | Drive-By Truckers | 3:51 | |
| A Song for You - 2002 Remaster | Gram Parsons | 5:00 | |
| Sweet Dark-Haired Man | Joan Shelley | 3:08 | |
| Mystifies Me - 2015 Remaster | Son Volt | 4:12 | |
| Hockey Skates | Kathleen Edwards | 4:28 | |
| King Of California | Dave Alvin | 4:50 | |
| One Thousand Miles | Pete Droge, Rhonda Vincent, Gillian Welch, Sara Evans, Bonnie Bramlett, The Blazers, Pete Drodge | 4:54 | |
| Mixtape | Tift Merritt | 3:18 | |
| Loretta - Live From The Ryman Auditorium, Nashville/2004 | Norah Jones, Gillian Welch, David Rawlings | 3:22 | |
| The West Was Burning | Martha Scanlan | 4:59 | |
